UNCLE BOONMEE WHO CAN RECALL HIS PAST LIVES (2010)

 




















Directed by: Apichatpong Weerasethakul
Starring: Thanapat Saisaymar, Jenjira Pongpas, Sakda Kaewbuadee, Natthakam Aphaiwong, Jeerasak Kulhong, Kanokporn Thongaram, Samud Kugasang, Wallapa Mongkolprasert, Sumit Suebsee, Vien Pimdee

114 minutes
(NR - strong language, adult themes, adult situations)
Country of origin: Thailand

PLOT:
Dying of kidney disease, a man spends his last, somber days with family, including the ghost of his wife and a forest spirit who used to be his son, on a rural northern Thailand farm.

TRAILER:

A PERSONAL JOURNEY WITH MARTIN SCORSESE THROUGH AMERICAN MOVIES (1995)

 

Directed by: Martin Scorsese, Michael Henry Wilson
Starring: Martin Scorsese, Allison Anders, Kathryn Bigelow, Francis Ford Coppola, Brian De Palma, Andre De Toth, Clint Eastwood, Jodie Foster, Carl Franklin, George Lucas, Gregory Peck, Arthur Penn

225 minutes
(NR - adult themes, adult situations)

PLOT:
Legendary filmmaker Martin Scorsese describes his initial and growing obsession with films from the 1940s and 50s as the art form developed and grew with clips from classics and cult classics.

KEVIN HART - WHAT NOW? (2016)

Directed by: Leslie Small, Tim Story
Starring: Kevin Hart, Halle Berry, Don Cheadle, Ed Helms, David Meunier, Joey Wells, Richardson Cisneros-Jones, Peter Mensah

96 minutes
(R - strong language, adult themes, adult situations, violence)

PLOT:
Comedian Kevin Hart performs in front of a crowd of 53,000 people at Philadelphia's outdoor venue, Lincoln Financial Field.

TRAILER:

 

GONE GIRL (2014)

 

Directed by: David Fincher
Based on the novel by: Gillian Flynn
Produced by: Arnon Milchan, Joshua Donen, Reese Witherspoon, Cean Chaffin
Starring: Ben Affleck, Rosamund Pike, Neil Patrick Harris, Tyler Perry, Carrie Coon, Kim Dickens, Patrick Fugit, Missi Pyle, Emily Ratajkowski, Casey Wilson, Lola Kirke, Boyd Holbrook, Lisa Banes, Sela Ward, Scoot McNairy, Scott Takeda, David Clennon, Kathleen Rose Perkins

149 minutes
(R - strong language, adult themes, adult situations, violence, graphic nudity)

PLOT:
Nick Dunne, a small-town guy who made good in the big city as a magazine writer blames the recession and the loss of his job for the decline of his marriage to his intellectually superior wife with a substantial trust fund. Questions of his motives and character begin to arise after his wife's disappearance on the morning of their fifth anniversary. As the search for his missing wife plays out over the ensuing days, guilty suspicions are fueled into a national frenzy by the media circus camped outside his house. Is this idyllic, everyman truly capable of murdering his wife?

TRAILER:

RHUBARB (1951)

 

Directed by: Arthur Lubin

Based on the novel by: H. Allen Smith

Starring: Ray Milland, Jan Sterling, Orangey the cat, William Frawley, Gene Lockhart, Elsie Holmes, Taylor Holmes, Willard Waterman, Henry Slate, James Griffith, Jim Hayward, Donald MacBride, Hal K. Dawson, Billie Bird, Paul Douglas

94 minutes

(NR - adult themes)

PLOT:

Rich, eccentric T.J. Banner adopts a feral cat who becomes an affectionate pet. Then T.J. dies, leaving to Rhubarb most of his money and a pro baseball team, the Brooklyn Loons. When the team protests, publicist Eric Yeager convinces them that Rhubarb is good luck. But Eric's fiancée Polly seems to be allergic to cats, and the team's success may mean new hazards for Rhubarb.

RUMBLE - THE INDIANS WHO ROCKED THE WORLD (2017)

 




















Directed by: Catherine Bainbridge, Alfonso Maiorana
Starring: George Clinton, Robbie Robertson, Gary Giddins, Martin Scorsese, Steven Van Zandt, Joy Harjo, Stevie Salas, David Fricke, Wayne Kramer, Taylor Hawkins, Beth Wray Webb, Sherry Wray, Ron Welburn, Billy Hancock, Taj Mahal, Slash, Iggy Pop, Antonio D'Ambrosio, Greg Laxton, Marky Ramone, Dan Auerbach, Jennifer Elizabeth Kreisberg, Pura Fe, Ulali, John Troutman, John Trudell, Guy Davis, John Sinclair, Big Chief Monk Boudreaux, Cyril Neville, Erich Jarvis, Ivan Neville, Joseph Hills, Rhiannon Giddens, Derek Trucks, Alvin Youngblood Hart, Malinda Maynor Lowery, Corey Harris, Scott Barretta, Quincy Jones, Bill Lester, Charlie Sexton, Buddy Guy, Julia Rinker-Miller, Chad S. Hamill, Tony Bennett, Garrin Hertel, Buffy Sainte-Marie, Gary Farmer, Bill Miller, Adam Beach, Janie Hendrix, Robert Trujillo, Billy Cox, John Selk, Bits of Bluegrass, Steven Tyler, Elliot Easton, Rickey Medlocke, Jim Keltner, Jackson Browne, Bob Glaub, Kelly Davis, Pat Vegas, Taboo, Apl.de,Ap, Mike Inez, Matt Sorum, Phil Soussan

103 minutes
(NR - strong language, adult themes, adult situations)

PLOT:
This powerful documentary about the role of Native Americans in contemporary music history, featuring some of the greatest music stars of our time, exposes a critical missing chapter, revealing how indigenous musicians helped shape the soundtracks of our lives and, through their contributions, influenced popular culture.

TRAILER:

THE CONQUERING POWER (1921)

 




















Directed by: Rex Ingram
Based on the novel "Eugenie Grandet" by: Honore de Balzac
Starring: Rudolph Valentino, Alice Terry, Ralph Lewis, Carrie Daumery, Bridgetta Clark, Mark Fenton, Ward Wing, Eric Mayne, Edward Connelly, George Atkinson, Willard Lee Hall

89 minutes
(NR - adult themes)

PLOT:
After losing his father, a playboy moves in with his miserly uncle, who seeks to cheat him out of his inheritance.

ACTUAL MOVIE:

DOUBLE DARE (2004)

 




















Directed by: Amanda Micheli
Starring: Jeannie Epper, Zoe Bell, Lynda Carter, Lucy Lawless, Eurlyne Epper, Ken Howard, Terry Leonard, Quentin Tarantino, Steven Spielberg, May Boss, Terry Frick, Conrad E. Palmisano

81 minutes
(NR - adult language, adult themes, adult situations)

PLOT:
Documentary about the struggles of two stuntwomen in male-dominated Tinseltown to stay working, stay thin and stay sane.

TRAILER: 

I'M KING KONG! THE EXPLOITS OF MERIAN C. COOPER (2005)

 




















Directed by: Christopher Bird, Kevin Brownlow
Narrated by: Alec Baldwin
Starring: Merian C. Cooper, David Strohmaier, James D'Arc, Paul M. Jensen, Ted Curtis Jr, Terry Moore, Rudy Behlmer, Ray Harryhausen, Harry Carey Jr, Ray Bradbury, Bob Burns, Craig Barron, James DeValera Mansfield, Daniel Selznick, David "Tex" Hill, Mark Cotta Vaz, James Karen

57 minutes
(NR - adult themes)

PLOT:
This documentary explores the incredible life of Merian C. Cooper, from his time as a soldier and pilot in three different wars, to his exploits in Hollywood, as a director, producer and cinematic innovator.

DARK MONEY (2018)

 

Directed by: Kimberly Reed

Starring: Jon Tester, Debra Bonogofsky, Jim Peterson, Ellie Hill, Amanda Curtis, Llew Jones, John Adams, John Ward, Ed Bender, Ann Ravel, Chuck Johnson, Jonathan Motl, Steve Bullock, Mike Wheat, Rick Vadi, Gabi Cote, Cheri Maclean, Verner Bertelsen, Jim Brown, Jim Nelson, Margot Barg, Tom Goldstein, Jeffrey Toobin, Trevor Potter, Art Wittich, Rob Cook, Sheila Krumholz, Mary Bottari, Paul S. Ryan, David Parker, Jaime MacNaughton, Gene Jarussi, John Heenan, Jeff Welborn, Ellen Weintraub, Lucinda Luetkemeyer, Sarah Arnold

97 minutes

(TV-14 - adult language, adult themes, adult situations)

PLOT:

This acclaimed documentary examines one of the greatest present threats to American democracy: the influence of untraceable corporate money on our elections and elected officials. The film takes viewers to Montana, a frontline in the fight to preserve fair elections nationwide, to follow a local journalist working to expose the real-life impacts of the U.S. Supreme Court's Citizens United decision.

TRAILER:

WILL & GRACE (1998 - 2020)

 




















Directed by: James Burrows
Created by: David Kohan, Max Mutchnick
Starring: Jim Abbott, Andrew Ableson, Ben Acker, Walter Addison, Shohreh Aghdashloo, Robert Aguilar Jr, Lori Alan, Ellen Albertini Dow, Kate Albrecht, Reed Alexander, Adrienne Alitowski, Keith Allan, Landry Allbright, Jerome Allen, Hira Ambrosino, Christian S. Anderson, Dion Anderson, Nathan Anderson, Todd Robert Anderson, Michael Angarano, Mark Ankeny, Fred Applegate, Kathleen Marie Archer, Alan Arkin, Ryan Armstrong, Will Arnett, Rosanna Arquette, Jorden Ashley, Jennifer Aspen, Richard Assad, Kevyn Aucoin, Debra Azar, Christopher Backus, Kevin Bacon, Penn Badgley, Tim Bagley, Steven W. Bailey, Leigh-Allyn Baker, Sunkrish Bala, Alec Baldwin, Doug Ballard, John Balma, Kirk Baltz, Karen Bankhead, Shawn Barber, Paris Barclay, Adam Barr, Sara Barrett, Cal Bartlett, Derek Basco, Dion Basco, Brooke Baumer, Orson Bean, Debra K. Beatty, Jacqueline Beatty, Emil Beheshti, Lisa Nicole Bell, Matt Bellner, Melinda Bennett, Chris Berg, Candice Bergen, Sandra Bernhard, Sydney Berry, Keith Biele, Jason Biggs, Jaimarie Bjorge, Jack Black, James Black, Bill Blair, Rita Bland, Jeff Blumenkrantz, Charlie Bodin, Corinne Bohrer, Alex Boling, Gabriel Bologna, Ashley Borden, Kyle Bornheimer, Zachary Bostrom, Mathew Botuchis, Dmitri S. Boudrine, Wil Bowers, Matt Bradshaw, Patrick Breen, Eileen Brennan, Eric Brenner, Cheryl Bricker, Beau Bridges, Kevin Brief, Rod Britt, Ivar Brogger, Elaine Bromka, Conroe Brooks, Trev Broudy, Robert Curtis Brown, Roscoe Lee Browne, Molly Bryant, Dan Bucatinsky, Patricia Bunch, Edward Burns, Jere Burns, Marcia Ann Burrs, Skyler Caleb, Dean Cameron, Bruno Campos, John Cantwell, John Capodice, Amanda Carlin, Ever Carradine, Deborah Carson, Pablo Cartaya, Veronica Cartwright, Heath Castor, Ben Caswell, Megan Cavanagh, Eric Cazenave, Richard Chamberlain, Matt Champagne, Kaine Bennett Charleston, Ali Chen, Cher, Shawn Christian, Mark Cirillo, Steven Christopher Clark, John Cleese, Bob Clendenin, Glenn Close, Karen Co, Annie Coffey, John Colella, Ryan Tyler Collier, Joan Collins, Andy Comeau, Noel Conlon, Harry Connick Jr, John P. Connolly, John David Conti, Kevin Cooney, Demitri Corben, Mark Correy, David Costabile, Robert Costanzo, Katie Couric, Franklin Cover, Jennifer Elise Cox, Mimi Cozzens, Matt Crabtree, Amy Crofoot, Macaulay Culkin, Sabrina Culver, Tim Curry, Lou Cutell, Jensen Daggett, Matt Damon, Kyla Dang, Blythe Danner, Christopher Darga, Clifford David, Gordon Davidson, Hugh Davidson, Geena Davis, Kristin Davis, Troy Davis, Timothy Davis-Reed, Ellen DeGeneres, Lea DeLaria, Christopher DeLisle, Jennifer DeMille, Anthony DeSantis, Jeffrey Patrick Dean, Jessica Dean, Patrick Dempsey, Doug Devine, Murphy Dylan Devine, Taye Diggs, Richard Dorton, David Doty, Michael Douglas, Gerald Downey, Jane Downs, Ralph Drischell, Minnie Driver, John Ducey, Bruce Dworkin, Christine Ebersole, Todd Eckert, Ashley Edner, John Edward, Hanni Eid, Helen Eigenberg, Kip Ellwood, Eugene Elman, Stephanie Erb, Wanda-Lee Evans, Kevin Fabian, Patrick Fabian, Jennie Fahn, Edie Falco, Stephanie Faracy, Amy Farrington, Roy Fegan, Jordan Feldman, Miguel Ferrer, Rick Ferro, Ayda Field, Lindsey Fields, Paul Fitzgerald, Markus Flanagan, Bridget Flanery, Julie Fleischer, Jodi Fleisher, Jon Fleming, Eileen Fogarty, Dave Foley, Raymond Forchion, Candy Ford, Nicole Forester, Jeremy Forte, Tiffany Fraser, Loren Freeman, Jesse Fremont Allis, Erin Fritch, Dan Futterman, Scott Kelly Galbreath, Stacy Galina, Rudy Galindo, Tom Gallop, Victor Garber, Andy Garcia, Lee Garlington, Chris Gartin, Brian Gattas, Dan Gauthier, Lynnette Gaza, Jackie Geary, Christopher Gehrman, Susie Geiser, Helen Geller, Tony Genaro, Gretchen German, Murray Gershenz, Luciano Giancarlo, Sara Gilbert, Keeshan Giles, Vanessa Ann Giorgio, Louis Giovannetti, Matthew Glave, Mary Pat Gleason, Jerry Goebel, Gigi Goff, Adam Goldberg, Jeff Goldblum, Lorry Goldman, Marcy Goldman, Burt Goodman, Steve Goodwillie, Nealla Gordon, John T. Grantham, Michael Taylor Gray, Seth Green, Clark Gregg, Michele Gregory, Richard Gross, Gary Grubbs, Eric Gustavson, Paul Gutrecht, Joyce Guy, Fiona Hale, Daryl Hall, Will Hall, Markus Hamilton, Thomas J. Hamilton, Rochelle Hannah, Mark Harelik, Woody Harrelson, Dustin Harris, Neil Patrick Harris, Megan Taylor Harvey, Steve Hasley, Scott Haven, Erinn Hayes, Reginald C. Hayes, Sean Hayes, Tim Hayward, James Healy Jr, Barry Heins, Lonnie Henderson, Lyn Alicia Henderson, Buck Henry, Erin Hershey, Chris Herzberger, Tim Herzog, Abraham Higginbotham, Gregory Hines, Hallee Hirsh, Victoria Hoffman, Bertha Holguin, Brian Howe, James Huang, Matt Huhn, Darlene Hunt, Bill Idelson, Ellen Idelson, Bryan Irzyk, Victor Z. Isaac, Judith Ivey, Janet Jackson, Brian Jacobs, Peter Jacobson, Hunter James, Hep Jamieson, Gary Janetti, Julie Janney, Brandon Jarrett, Aytl Jensen, Elton John, Christopher Jones, James Earl Jones, Jamison Jones, Kathryn Joosten, Anthony Jordan, Leslie Jordan, Yvans Jourdain, Mark Juliano, Sachiyo K, Jamie Kaler, Jay Kanzler, Mitch Kaplan, Alex Kapp, Barry Karas, Philipp Karner, Lyndon Karp, Lainie Kazan, Josh Keaton, Paul Keith, Jovial Kemp, Patrick Kerr, Laura Kightlinger, Athena Kihara, Jesse King, Perry King, Jon Kinnally, Kelli Kirkland, Terry Kiser, Butch Klein, Jono Kohan, Steven Koller, Eric Allan Kramer, Kristina Krofft, Jason Landau, Michael Atlas Lane, Peggy Lane, Beth Lapides, J.T. Larsen, Matt Lauer, Piper Laurie, Adam Lazarre-White, Lela Lee, Michele Lee, Carol Leifer, Hannah Leigh, Katrina Lenk, Ken Lerner, Roz Lerner, Susan Leslie, Clinton Leupp, Phil Levesque, Jerry Levine, Hal Linden, Jessica Lindsey, Ralph Litt, Barry Livingston, Richard Livingston, Kari Lizer, Jennifer Lopez, Traci Lords, Jason Ryan Lovett, Marjorie Lovett, Rebecca Lowman, Patti LuPone, J. Lucas, Josh Lucas, Michael Lucas, Tim Lucason, Aaron Lustig, Natasha Lyonne, Raymond Ma, Seth MacFarlane, Melonie Mack, Peter Mackenzie, Madonna, Lee Majors, Claire Malis, Marshall Manesh, Camryn Manheim, Barry Manilow, Jennifer Manley, Cynthia Mann, J.P. Manoux, Henriette Mantel, Alan March, Manny Marianakis, Ken Marino, Kenneth Mars, Jason Marsden, Alison Martin, Millicent Martin, Cyndi Martino, Marissa Matrone, Blythe Matsui, Jamisin Matthews, Mickey Maxwell, Reiley McClendon, Eric McCormack, Matthew McCray, Jennette McCurdy, Dylan McDermott, Mary Beth McDonough, Joel McHale, Julian McMahon, Heather McPhaul, Anne Meara, Michael Medico, Anthony Paul Meindl, Michael Merton, Debra Messing, Bess Meyer, Craig A. Meyer, Terrence Michael, Larry Michelson, Christian Middelthon, Thomas A. Miller, Adrian Mojica, Abe Molinares, Debra Mooney, Christina Moore, Demi Moore, Martin Morales, David Moreland, Gina Morelli, Michael Morris, Phil Morris, Robert Michael Morris, Bob Morrisey, Shelley Morrison, Marianne Muellerleile, Oliver Muirhead, Megan Mullally, Morgan Nagler, Titus Napoleon, Martina Navratilova, Judy Nazemetz, Tracy Nelson, Nick Nervies, Bebe Neuwirth, Ben Newmark, David Newsom, Thi Nguyen, Troy Norton, John O'Brien, Tara O'Connor, Rosie O'Donnell, Katie O'Rourke, John Oates, Joe Ochman, Nick Offerman, Shandra Olds-Whitlow, Jim Ortlieb, Sharon Osbourne, Mary Ostrow, Gordy Owens, Peter Paige, Brian Palermo, Sam Pancake, Paul Parducci, Corey Parker, Shane Partlow, Tony Pasqualini, Scott Patterson, Kevin Paul, Sara Paxton, Steve Paymer, Jo Marie Payton, Chris Penn, Kerry Perdue, Don Perry, Luke Perry, Bernadette Peters, LaMonica Peters, Steven Petrarca, Rachelle Pettinato, Michael Philip, Jason Pierce, Maria Pitillo, Jeremy Piven, Patricia Place, Suzanne Pleshette, Larry Poindexter, Sydney Pollack, Donna Ponterotto, Julie Pop, Ray Porter, Parker Posey, Tom Poston, Chris Potter, Joan Jaffry Pousi, Joan Poust, Paolo Presta, Shirley Prestia, Megyn Price, Liz Prives, Rachel Quaintance, Will Radford, Christopher Randolph, Betty Rae, Jim Rash, Ben Reed, Carla Renata, Debbie Reynolds, Gigi Rice, Andy Richter, Tia Riebling, John Riggi, Gary Riotto, Julius Ritter, Chita Rivera, Lance Roberts, Kim Robillard, Kali Rocha, Michael E. Rodgers, Al Roker, Robert Romanus, Wells Rosales, Andrew Rosenbach, Eric Roth, Brandon Routh, Hansford Rowe, Chuck Roy, Sara Rue, Bob Rumnock, Bob Rusch, Melissa Russell, Emily Rutherfurd, Steve Ryan, Daryl Sabara, Dan Sachoff, Tony Sagastizado I, Miguel Sagaz, David St. James, Fred Sanders, Ethan Sandler, Steve Sandoval, Kevin Sateri, Dennis Satterfield, Paul Satterfield, Mimi Savage, Frank Saverino, Connie Sawyer, Raphael Sbarge, Margaret Scarborough, Lauren Schaffel, Will Schaub, Wendy Schenker, Steve Schroeder, Mario Schugel, Earl Schuman, Heidi Schultz, Uwe Schwarzwalder, Kimberly Scott, Tom Everett Scott, Michael Scovotti, Brian A. Setzer, Chloe Sevigny, Brent Sexton, Dirk Shafer, Molly Shannon, Hope Shapiro, Jimmy Shaw, Steven Shaw, Christopher Shea, Jan Sheldrick, Steven Shenbaum, Danica Sheridan, Nicollette Sheridan, Todd Sherry, Helen Siff, Jamie-Lynn Sigler, Douglas Sills, Andrea Silvers, Trisha Simmons, Kevin Sizemore, Helen Slater, John Slattery, Jeri Slaughter, Gil Smith, Mira Sorvino, Britney Spears, Wendie Jo Sperber, Stephen Spinella, Monika Spruch, Benjamin Sprunger, Michael Stadvec, Todd Stashwick, Benjamin Steeples, Charles C. Stevenson Jr, Eric Stoltz, Sharon Stone, Claude Stuart, Jason Stuart, George Stults, Greg Suddeth, Larry Sullivan, T.F. Sullivan, Cory Surovy, David Sutcliffe, Wanda Sykes, Symba, George Takei, Rip Taylor, Josh Temple, Jon Tenney, Maria Thayer, Sonya Theriault, Michael Edward Thomas, Mic Thompson, Preston Thompson, Justin Thorne, Kenneth Tigar, John H. Tobin, Stephen Tobolowsky, Tamlyn Tomita, Lily Tomlin, Rip Torn, Stuart Townsend, Michael D. Trail, Robbie Troy, Lauren Tuerk, Dale E. Turner, Pamala Tyson, Adam Ullberg, Tracey Ullman, Andy Umberger, David Vaillancourt, Steve Valentine, Harry Van Gorkum, Sara Van Horn, Lucky Vanous, Mariam Vardanyan, Greg Vaughan, Reginald VelJohnson, Julia Vera, Tom Verica, Neil Vipond, Jared Farid Ward, Leslie Ann Warren, Steven Weber, Cody Weiant, Brett Weir, Dan Wells, Richard Wharton, Maggie Wheeler, Cheryl White, Irene White, Kara Naomi White, Gene Wilder, Seemah Wilder, Kathleen Wilhoite, Joseph Will, Branden Williams, Casey Williams, Kenneth Alan Williams, Matthew J. Williamson, Geoff Wingham, Jase Wirey, Paul Witten, Jeff Witzke, Tommy Woelfel, Karl T. Wright, Keone Young, Christian Zimmerman, Rose Abdoo, Brian Jordan Alvarez, Jill Basey, Vanessa Bayer, Emilio Borelli, Barry Bostwick, Preston Bradley, Andy Buckley, E.J. Callahan, Emily Churchill, Fred Cross, Dana DeLorenzo, Katarina Demetriades, Natalie Dreyfuss, Carly Dutcher, Doc Farrow, Andy Favreau, Beanie Feldstein, Derek Gaines, Michael Galante, Geovanni Gopradi, Max Greenfield, Paul Gregory, Gerren Hall, Ramone Hamilton, Ian Harvie, Cheyenne Jackson, Jordan Julian, Jet Jurgensmeyer, Robert Klein, Buz Kohan, Matt Letscher, Ken Luckey, Jane Lynch, Gregor Manns, Mackenzie Marsh, Rasika Mathur, Eddie Matos, Mary McCormack, Jack McGee, Joshua Meltzer, Kate Micucci, Jaseida Mojica, Cody Rain Murray, Alexa Nisenson, Evan O'Toole, Dyana Ortelli, Sean Owens, Edward Padilla, Ryan Pinkston, Ben Platt, Lidia Porto, Brian Posehn, Anthony Ramos, Andrew Rannells, Chris Redd, Sharon Sachs, Davi Santos, Justin Shaw, Lisa Y. Sheeler, Mitch Silpa, Jason Sims-Prewitt, Sterling Sulieman, Robert Towers, Victor Turpin, Lauren Weedman, Danielle Weeks, Zack Weinstein, Colette Whitaker, Jett Wilder, Jay Brian Winnick, Chaz Ahern, Carrie Aizley, Bruno Amato, Pyar Anderson, Michael Andricopoulos, Carlos Antonio, Elando Baltimore, Scott Beehner, Matt Bomer, Adwin Brown, Jeffrey Cade Ross Brown, Maria Carmen, Aya Cash, A.J, Castro, Juliet Cesario, Carlie Craig, Jon Cryer, Yelyna De Leon, Christian Di Salvo, David Douglas, Charles Emmett, Samuel Faraci, Barrett Foa, Cleo Fraser, Ben Giroux, Jake Green, Brad Grunberg, Iyad Hajjaj, Seth Hampton, Chelsea Handler, Alice Hirson, Martha Kelly, Jennifer Kenyon, Nicola Lambo, Deborah Levin, Andrea Martin, Aly Mawji, Karen Y. McClain, Amari O'Neil, Joy Osmanski, Mike Nojun Park, Adrieanne Perez, Selah Phillips, Shiloh Phillips, Ruben Pla, Adam Rippon, Devere Rogers, Irene Roseen, Gabrielle Sanalitro, Julie Schmid, David Schwimmer, Reid Scott, Connie Shin, Tucker Smallwood, Winston Story, Alfredo Tavares, Livia Trevino, Victoria Van Fleet, Dan Warner, Samira Wiley, Tony Amendola, Aleksei Archer, Lucie Arnaz, Jocelyn Ayanna, Sarah Baker, Patricia Belcher, Paul Ben-Victor, Charles Berthoud, Erik Betts, Karina Bonnefil, Tabitha Brown, Yvette Nicole Brown, Kevin Scott Cannon, Tim Cannon, Hollis W. Chambers, Antonio D. Charity, Matt Cook, Rebecca Corry, Katherine Cozumel, Navaris Darson, Sophie Fatu, Caroline Fife, Peter Graham, Scott Icenogle, Theresa Ireland, Jeff Jocoy, Brian Michael Jones, Gus Kenworthy, Earl T. Kim, T.R. Knight, Eva La Dare, Drew Lipson, Billie Lourd, Demi Lovato, Alessandro Marino, Jaime Moyer, Gracen Newton, Christian Ochoa Lavernia, Patton Oswalt, Chris Parnell, Eddie Pepitone, Ryan Phillippe, Aileen Quinn, Frankie A. Rodriguez, Seth Rudetsky, Major Mike Russell, Meredith Salenger, Tim Scarry, Aryan Simhadri, Allison Smith, Dylan Riley Snyder, Nicole Sullivan, Anna Suzuki, Christopher Thornton, Pej Vahdat, Randy Vasquez, Alex Wells, Alexandra Wentworth, Persia White, Wayne Wilderson

228 episodes
(TV-14 - adult language, adult themes, adult situations)

PLOT:
Gay lawyer Will and straight interior designer Grace share a New York City apartment. Their best friends are gleeful and proud gay Jack and charismatic, filthy-rich, amoral socialite Karen.

season 1 -
Grace gets an unexpected marriage proposal and her best friend Will deals with his own feelings about her proposal. Will advises Grace against marrying Danny and she freaks out. With nowhere to stay, Grace turns to Will for shelter. First he dismisses her idea of living together, but later agrees. Will's friend Jack meets Grace's assistant Karen. Grace makes plans to create one large bathroom out of her and Will's individual spaces in the apartment. Will dislikes the idea, but forces himself to agree to prove that he knows how to compromise. The change leads to Will revealing his fears about why his relationships end in failure. Meanwhile, Jack needs help working on his resume, and Karen reluctantly takes on more responsibility in Grace's office. Grace designs a room for Will's boss, Harlin, which Will dislikes. Jack begins his singing career with his first show of Just Jack. On Halloween, Will and Grace plan to ignore the holiday--but they are forced to baby-sit Harlin's two children, and eventually get into the spirit of the evening. Jack and Karen dress up and spend a night on the town, and Karen becomes very popular with some drag queens. Grace brags that she and Will are the best of friends, with no secrets from each other--but when Jack reveals that Will briefly had an affair that Grace didn't know about, she becomes fearful that he might be hiding things from her. Karen privately hires Will when she begins to consider divorcing her husband Stanley, and her insistence on secrecy only makes Grace more paranoid. Grace fears that Will is the reason that she has no interest in dating men. Jack faces trouble when the IRS catches up to him regarding his tax evasion. Grace asks for Will's help in buying the studio that serves as her office space. They end up competing to see who can get the lowest price from the owner. Jack begins a career in massage therapy, taking on Karen as his first client. Grace feels left out when all of her friends talk about their dogs, so she adopts an adorable Yellow Lab puppy. Though Will initially hates the idea, he soon becomes obsessed with the puppy, and Grace realizes that he is lonely for companionship. Meanwhile, Karen and Jack become the puppy's dogsitters, and Karen has some fun by thinning Grace's closet of outfits she deems ugly. Will and Grace find entertainment in listening to the conversations through their heating vent. Jack writes and performs a play that expresses his dismay over the fact that Will and Grace are ignoring him. It's Will's birthday, and everyone goes to see Champions on Ice--even though Will doesn't want to (but pretends that he is okay). Grace and Jack find a mutual interest in figure skating. When Grace nears a nervous breakdown during a design competition, Will hires a cleaning lady named April to organize the apartment. Grace soon becomes dependent on April's odd brand of moral support, frustrating Will. Jack lands a date with a cute graduate student in a bookstore, but inadvertently ruins a potential relationship when he pretends to be a lawyer. Grace's mother Bobbi, an actress with a big ego, comes to town for a visit and drives Grace crazy with passive-aggressive criticisms and suggestions, such as her marrying Will. But it's Will who hurts Grace most of all when he remarks that even if he was straight, he wouldn't want to be her husband. Karen finds out that her period is late, and faces conflicting emotions about her possible pregnancy. Will refuses to reconnect with his estranged brother, Sam. Grace and Sam have a fling. Will finds out about Grace sleeping with his brother, and although he's initially upset, he comes to terms with the fact that he really has not right to tell her who she can and can't sleep with. Will and Grace invite the same man over for a dinner date, and struggle while determining if he is straight or gay. Karen has to fire her driver. Grace organizes an apparently spontaneous weekend getaway for her, Will, Jack, and Karen to the mountains at Karen's cabin, but the real reason is more emotional: the trip coincides with what would have been Will and Michael's anniversary. Problems arise when Grace runs into an old friend named Campbell, and she finds herself torn between pursuing him and supporting Will, who eventually admits that he does still miss his ex-boyfriend. While Grace is consumed by work, Will befriends another woman in the building, Val Bassett. Jack is sentenced to community service for slapping a meter maid. When Jack joins Will and Grace's gym, Will becomes upset by his flamboyant behavior and transparent homosexuality, and even calls Jack a fag, a statement which Jack inadvertently overhears. Jack accuses Will of being reluctant to accept his own gayness, and Will is forced to consider that he may be right. Karen and Stan face marital troubles, so Grace suggests she spend some time with a girlfriend to feel better--and ends up inviting Karen over for a night of drinking and bonding. Grace is hired by an arrogant publicist under the condition that he gets a date with Will. Will accuses Grace of having too much competitiveness at their game night. Grace tries losing, but proves that Will is just as competitive. Jack teaches Karen CPR, which she reluctantly uses to save a man's life. After Grace temporarily gets back together with her ex-fiance, Grace and Will realize that their living together may be preventing them from finding mates. Jack marries Karen's maid Rosario so that she can stay in the country.

season 2 -
Grace moves into an apartment across the hall and decides to throw a party without Will's help to show her new-found independence. Will stresses about a date with a man from a bookstore. Jack has to move in with Rosario in Karen's apartment to make things look good for the INS. When Grace finds out that Will, acting as tenant board president, is the only tenant with a working fireplace, she decides to run against him in the upcoming election and take him down a notch or two in arrogance. They run an ugly race, slandering each other and buying vote, and in the end Grace wins when the two of them pester the last tenant for his vote while he's in his hospital room. But Grace isn't sure she wants the position when Will actually seems psyched to not have the job anymore, and she starts being pestered by all the tenants. Karen lets Guapo, the parrot out the window by mistake, and goes on a buying spree for Jack to make it up to him. When Guapo comes back, Jack hides the bird in the closet so that he can keep getting expensive gifts from Karen. Karen finally gives him the keys to an expensive boat, and he finally feels so guilty that he tells her what he did, and then she tells him that she actually knew all the time because she had video cameras everywhere. And the keys are only to Grace's office anyway. Grace is written up in the newspaper with an accompanying picture that makes her look much bustier than she actually is. When an old high school crush calls her and asks her out, she is incredibly excited until Karen points out that she'll now have to live up her published dimensions. With Karen's help she buys a water-filled bra that makes her look much larger up front than she is, but she springs some leaks while on her date at the art gallery and has to admit to her crush that she's wearing a water-bra. He calls her too shallow for his taste and quickly ditches her. Jack finds out that Will hooked up with his ex-boyfriend Walter and dumps Will as a friend because Walter was the love of his life. Will feels terrible, and tries to arrange a reconciliation between Jack and Walter, but when he does so it turns out that Jack was thinking about someone else and he isn't interested in Walter at all. Grace's mom comes to town and Grace is scared that her mom will try to set her up again. It turns out, however, that her mom is more interested in setting up Will with someone. Grace looks at this as an opportunity to show her mother how bad she is at setting people up, but is horrified when Will actually gets along with the guy. Grace finally admits that even though she's been telling her mom to stop setting her up for years now, she feels bad that her mother has actually stopped. Jack and Rosario are being interviewed by the INS to make sure their greencard marriage is for real, but it turns out their interviewer is somebody that Jack has met and hooked up with before. Luckily, Jack makes a big show of his love for Rosario, and the INS officers passes them just for trying so hard. Will's ego inflates after closing a major deal for Harlin, and he decides to focus solely on the millionaire's business by dumping all of the smaller clients who supported him when he first became a lawyer. But Will gets a harsh lesson when Harlin decides to fire him, leaving the lawyer without any prospects. Stan puts Karen on a budget to stop her wild spending, and she becomes terrified when Grace takes her to an outlet mall to teach her how to shop smarter. Jack challenges Will to become a cater-waiter on his staff, but when Will finds out that the catered event is for the American Bar Association, he backs out and joins the dinner guests. However, when one of Will's acquaintances starts treating Jack horribly, Will stands up for his friend and rejoins the wait staff. Grace finds out that Karen once starred in a fetish video, causing Karen to be so embarrassed that she quits her job as Grace's assistant. Grace placates Karen by finding and buying all the copies of the video and giving them to Karen... but of course she keeps one for herself. Will invites Jack's mother to Thanksgiving dinner as a surprise, only to discover that Mrs. McFarland doesn't know her son is gay; instead, Jack has claimed that he and Grace used to date. Will and Grace encourage Jack to tell the truth, while Karen is more upset by the fact that he chose Grace to be his imaginary girlfriend instead of her. When Jack finally works up the courage to confess, his mother reveals a secret of her own. Grace looks to Will for representation when a famous lawyer, Ben Doucette, doesn't pay her for a consulting assignment. Will ends up getting a job offer, and when he accepts it, his first job is to make Grace's claim go away. Under protest, he takes on the assignment, but when Grace is about to get screwed, he backs down and can't go through with it. Ben tells Will that it was actually all a test of Will's character, and ends up giving Grace the money she's owed and letting Will keep his new job. Jack gets a part in a sexual harassment education video, but when his co-star falls ill, Karen takes her place. Karen discovers during filming that Jack's tongue can do miraculous things in her ear, and it takes them 147 takes to get the video right. After they're done filming, Karen shows Jack what she can do with HER tongue in HIS ear, and they trade ear favors back and forth. Will and Grace tire of their boring friends Rob and Ellen, and instead bond with Kai and Naomi, a hip young couple who introduce the pair to New York's nightlife. When Rob and Ellen find out that Will and Grace have been lying to them, they leave in a huff--and leave the latter two in an uncomfortable position when Kai and Naomi's wild partying proves too much for them. Karen drags Jack along when she attends a parent-teacher conference at her children's school, and a chance encounter with a sensitive young boy named John helps Jack face his traumatic experiences as a victim of bullying. Will has until Friday to find a new client or lose his job, so he finds himself kissing Karen's ass to get her husband's business. Jack and Grace use a crappy teapot to get on their favorite TV show, Antiques on the Road (Antiques Roadshow). When they find out, to their surprise, that the teapot is worth $30,000, they fight over it, breaking someone else's valuable antique and having to give up the teapot in payment. Grace is upset when Will's best friend from high school comes to visit from Paris and asks Will to be the father of her baby. Grace realizes that it's partly because she's worried about Will having a child growing up so far away, but even more than that, she sort of always thought of Will as her backup sperm in case she never met a man she wanted to marry and have kids with. Will calls her selfish when she tells him this, but then he realizes that he always thought of Grace as his backup eggs, and if he ever has a kid he wants it to be with her. Will is terrified when he starts having erotic dreams about Grace, and starts seeing a therapist to solve the problem. The doctor's apparently innocent suggestion to bring Grace in for a session becomes tense when he starts dating her, which leads to frustration for Will--and a solution to the causes of his nightmares. Jack wants Karen to treat Rosario better, but is surprised to discover that both are happier when they're arguing and fighting with one another. Will's father comes to town to accept a lifetime achievement award from his company. Will, who has always gotten along well with his father, takes Grace to the ceremony to surprise his dad. He finds out that his dad has been telling all his colleagues that Will is straight and married to Grace. Although Grace attacks the role of Will's wife with relish, Will confronts his father about the lie. Will tells his father that he understands that he had to do what he had to do, and guilts his father into basically turning his entire award-acceptance speech into a diatribe on how much he loves his gay son. Will's father's appearance reminds Jack of the fact that he has no idea who his biological father is. Karen takes it upon herself to hire a private investigator and finds Jack's dad. She sets up a mysterious meeting for them, and they start hitting on each other before Karen shows up and tells them why they're actually meeting. The mysterious man claims that he's gay and always has been, and so couldn't possibly be Jack's dad, so they plan a date instead of a family reunion. When a scheduled kiss between two gay TV characters doesn't happen, Jack gets very upset and convinces Will to protest at NBC with him. When they are rebuffed by the president's office, they see Al Roker doing "The Today Show" on the streets of New York, and go to talk to him. When Al ignores Jack asking how long he will have to wait to see a gay kiss on TV, Will grabs Jack and kisses him. Grace can't find a way to break up with her very sweet but very annoying boyfriend, Josh. She finally takes Karen's advice and tells Josh that she's in love with Will... right before they see Will kissing Jack on national television. Ben sets up Will on a blind date, and Will reluctantly goes. Will and his date Charlie actually get along, but when Charlie doesn't call after three days, Will fears he's a bad date. After Jack gives Will some terrible counseling on how to be a better date, Jack finally tells Will that he should call Charlie and not be a wuss and wait for him to call. Just as Will finally gets the guts up to call, he sees Charlie in the very restaurant where he's eating with Jack. Grace is happily dating Josh, but would like to change some things about him like his cheap "nature" gifts and his indecisiveness. Karen recommends Grace try withholding sex to implement her changes, and against her better judgement, Grace does so and Josh breaks up with her. When Josh comes storming into her office ranting about how he won't change for anyone and she has to take him as he is, his decisiveness and forcefulness turn her on and she jumps him. Will's former boyfriend Michael is back in town and they run into each other since Grace is decorating Michael's new apartment. Will feels like he gets a vibe from Michael that he might be interested in getting back together, so he goes over to Michael's place and makes a fool of himself when he meets Michael's new boyfriend. Will blows up at Grace for not telling him about it, when he's actually upset with himself over the fact that Michael has moved on and Will doesn't seem to be able to. Karen has aspirations of being an interior decorator, and wants to be the one to decorate Michael's apartment, but Grace is only willing to let her do one chair, which is enough to make Karen's head spin. Will is on a date with a friend of the family who is incredibly annoying, and has Grace call him with a fake emergency to get him out of it. It turns out Grace's emergency is real when Karen's husband Stan is admitted to the hospital with a supposed heart attack. Will, Grace, Jack, and Rosario are in the waiting room arguing over who Karen will turn to for support, and they end up making a bet on it. Meanwhile, the doctor not only informs Karen that her husband is fine and didn't have a heart attack, but tells her about her friends making the bet. In order to torture them, Karen gets them all to do things they hate: Grace gives blood, Rosario cleans the hospital, Jack cuts up his credit cards, and Will makes nice to his annoying date of earlier. Then she lets them know that they tried to play with her, and she won, and reminds them that she doesn't do emotion. She does, however, end up breaking down to Grace at the end. Grace begs God to help her and Will win Joni Mitchell concert tickets, and so when they actually win, Grace convinces Will to help direct a kids' play at a local church. When the play performance time is moved to coincide with that of Joni Mitchell concert, Grace bags the play for the concert. Grace ends up showing up in time for the play because she got kicked out of the concert for singing too loud. Pushed by Grace, Jack helps Karen donate some clothing to charity. Jack accidentally donates Karen's favorite Chanel sling-back heels, and Karen goes to retrieve them. She and a homeless woman each find one of the shoes at the same time, and Karen bargains the woman down to five to get her other shoe back. As Karen is counting out hundreds, she hears the woman murmur how five dollars will make her day. Karen gives the woman the five dollars, and then gives her a few hundred on top when she sees how much the woman values the tiny amount of money. Will & Grace's best friends, Rob and Ellen, announce that they're getting married. Rob asks Will to be his best man, and Will happily accepts. Ellen asks Grace to be her maid of honor, and Grace stumbles around awkwardly for a moment before agreeing. When the happy couple leaves, Grace tells Will that she and Rob slept together the last time Rob and Ellen broke up. Later, Will is throwing the bachelor party while a guilty Grace has the bridal shower. Jack freaks out when the stripper at the bachelor party gives him a lap dance that actually turns him on, but is relieved when he finds out that the stripper is actually a preoperative transwoman. Ellen overhears Will and Grace talking about the fact that Grace slept with Rob, and freaks out, calling Rob and Grace terrible names and saying the wedding is off. After Ellen tries to seduce Will to even the score, Rob and Ellen finally make up in Will's bed. Grace and Val unexpectedly bond over their miserable Saturday nights, and become friends. However, when Grace's music box goes missing, she suspects Val, and convinces Will to snoop in her apartment. At a club, Jack meets Bill, and is disgusted to find out he is running a support group for ex-gays. To woo him, he and Karen infiltrate the meeting as a straight couple. Will and Grace visit an old college professor and his female best friend, and fear that they will become just like them once they are old. Jack and Ben help Karen learn how to cook, but the two men start competing over everything. Jack asks for Will's help in funding a product that he has designed. Grace goes for a job against a high-profile designer. Will and Jack go into business together to market a subway butt-pillow. Will tries to get Grace and his boss, Ben, to get along, and they get along so well that they end up in bed together. Will decides he's not going to freak out about it. Rosario tells Jack that she wants a divorce so she can marry the gardener. Jack decides to sue Karen to keep him in the lifestyle that he's become accustomed to. Will helps Jack, but Ben tells him he can't because Karen is their client. On top of this, Will discovers Ben cheating on Grace, so he quits his job. Will realizes that Ben and Grace are actually both dating other people, and are both okay with this. He can't believe he quit his job over this. Jack loses miserably in his lawsuit against Karen, and so he moves in with Will. Due to all the crises with his friends, Will keeps putting off a date with a cute lawyer he met until the cute lawyer finally gives up on him. Will is depressed with his life, although glad that he can finally tell Karen off now that she's no longer a client since he quit. Will runs away to a tropical island, leaving Jack and Grace bereft. Ben hunts him down and gives him everything he asks for so that he'll help a client on the tropical island with some tax problems. The client turns out to be Karen.

season 3 -
Will gets sick of Karen bugging him and returns from the tropics to find Jack not only taking his place in his apartment, but also taking his place as Grace's best friend and confidant. Will is jealous until Grace assures him that her love for him will never fade. Grace has been dating both Ben and Josh all summer, and thinks it's time she made a choice. Her choice becomes easier when she finds out Jack screwed around with Josh. On her way back into the country, Karen lets Rosario take the fall for her smuggling in some black pearls. Grace has to convince Karen to get Rosario out of jail by reminding her how much Rosario does for her. When someone tries to break into Grace's apartment, she moves in with Will and Jack. Will can't stand living with two other people, so he tells his two friends that one of them will have to move out, and they get to decide which one. After Grace and Jack duke it out for a while, they finally agree that Grace will move back across the hall. When Will hears their decision, he asks Grace to stay with him and suggests that Jack move into Grace's old place. Jack and Karen are still feuding since Jack tried to sue Karen. Will convinces Karen to forgive Jack, and although at first Jack doesn't accept the apology, the two end up bonding over their mutual love of laughing at other people's misfortune. When Grace joins Ben at the yacht club and sees Karen there, she finds out from Rosario that Karen is insecure because she is reaching the age of Stan's first wife. She tries complimenting Karen to boost her failing ego, but Karen just thinks Grace is a lesbian, so Grace asks Ben to flirt with Karen. Ben successfully does so, but when Stan sees him he gets jealous and has Ben thrown out of the yacht club. Will and Jack go to what they think is going to be a crazy gay weekend in the Hamptons, but what they find is that all of their crazy friends have settled down and are raising babies. Will volunteers himself and Jack to babysit for a night and is disappointed with the results, concluding that he'll make a terrible father. Jack reassures Will that he'll be a great father someday because he's already a great father to Jack. Grace gets a young intern in her office who worships Grace and her work, but Grace's delight is short-lived when the intern quickly remakes herself in Karen's image. Meanwhile, Will is putting together a skit for gay sensitivity seminar for the local police, and asks Jack to act in it along with two lesbians Jack doesn't get along with. Jack manages to remain polite to the lesbians as an acting challenge from Will, but when Will makes fun of Jack's character voice, Jack loses it and insults the lesbians in front of the police audience. Jack and Will end up in a screaming fight that they are terribly embarrassed about, but it turns out that their real insults are actually educational as well. Grace decides she doesn't love Ben and she should break up with him, but when she does so he refuses to let her. Finally, with help from Karen, Grace convinces herself that she does love Ben, but then Ben breaks up with her. Jack has a new cabaret act, Jack 2000, which does terribly until he adds stand-up that makes fun of Will's personal life. Will is insulted, and stops telling Jack details about his personal life. Jack's act fails when he has no new material and he's depressed about his best friend being mad at him. Karen convinces Will to help Jack out, and Will gives Jack permission to use even his most embarrassing moments, but Jack, reminded of what a good friend Will is, doesn't use them. An old boyfriend of Grace's named Nicholas comes into town with his new girlfriend and asks Grace to join them for a threesome. When Will and Karen laugh at the thought of Grace in a three-way, she decides to go through with it, but backs out at the last minute. Jack, working his new job at Banana Republic, meets a gorgeous man who is such a "smarty" that he can't approach him. Jack uses Will for a Cyrano de Bergerac move and lets Will's words come out of his mouth. Jack soon realizes that his target, Matthew, is boring to him, and Matthew soon realizes that Will is just his type and gives the embarrassed lawyer his card. At Will's birthday dinner the waiter is so rude that Grace complains about him and ends up getting him fired. She feels so badly that she hires him on as her office assistant, but then she's even more disappointed when she finds him dealing pot out of her office. Will sees a psychic who is so strangely right about things that he believes her when she says that he is going to spend the rest of his life with a man that he already knows named Jack. Will is horrified at the thought of spending the rest of his life with Jack, but then he and Jack realize that they could spend the rest of their lives together like the friends they are now. Jack finally gets to meet his idol, Cher in a café, but mistakes her for a drag queen Cher-imitator until she slaps him. In order to help a confused girl who doesn't realize she is dating a gay man, Will and Grace tell the story of when they dated in college, and Will didn't come out of the closet until after proposing to Grace and meeting her entire family as her fiance. Grace realizes how shallow she is when she breaks up with a guy she likes just because he has six toes on one foot. She then fears the worst for her present relationship after a minor medical procedure leaves her with a sore on her lip. Will and Jack find out that they're dating the same man. Karen tries to buy a Christmas present for her step-son. Will is tired of always paying for things for Grace, and when they go to their friends' civil union ceremony, he refuses to put her name on the gift he bought. They fight about it, and eventually it comes out that Will feels like Grace is his wife, and he doesn't want that. They make up when they do a reading together about love during the ceremony that brings home to them how they feel about each other. Jack gets addicted to caffeine when he has a crush on a guy who works at a coffee shop. Karen tries to help him kick the habit, but they're both in trouble when they find out that the commitment ceremony is alcohol-free and there's only a coffee bar. Will and Grace meet Sandra Bernhard by posing as prospective buyers of her apartment. Jack ends up in a bidding war for Britney Spears' sneakers, while Karen tries to support her stepson Mason in his swimming games. Sandra tells Will and Grace they resemble Dharma & Greg. Will finally calls Matt, the sports writer he met at Banana Republic forever ago, and they go out on a date. Matt mentions that one of the things he didn't like about his ex-boyfriend was that he hated sports, so Will pretends to be a big jock. Will tries desperately to get better at baseball by going to the batting cages, but only Grace can actually hit a ball. Will and Matt play basketball together and Matt totally busts Will as someone who doesn't like sports. Will explains why he pretended and Matt is surprised that Will thinks he's that shallow. Matt assures Will that they can still date even if Will isn't into sports. Grace forges a note from her therapist saying that she's crazy to get out of jury duty. Karen and Jack ask Grace to redecorate Jack's apartment but they are extremely difficult clients. They accidentally read the note from Grace's therapist and believe that she's actually crazy. She figures out that they read it and uses the fact that they're scared of her to do great work on Jack's apartment without their interference. When she's done, she admits to them that she tricked them but they don't believe her when she says she's not crazy. Will is upset when his boyfriend, Matt, introduces him to his boss as his brother and their relationship becomes strained because Matt is still in the closet. He tries to break up with Matt, but is so desperate for male affection that he wimps out. Grace tries to stand strong for him and be his conscience. When Matt's boss asks Matt straight out if he's gay and Matt denies it in front of Will, Will (by pretending to be Matt's brother as they have a serious discussion in front of his boss) tells Matt that the only way for their 'relationship' to work is if they were both open and honest, hoping for Matt to come out to his boss about his sexuality as well as his relationship with Will but Matt is reluctant to do so. Will is finally so disgusted that he breaks up with Matt. Karen is upset when she finds a copy of Stan's will and realizes that a third of her husband's money is being willed to charity. She blames her husband's bleeding heart lawyer, Will. Jack is misled by a postcard he gets from his mother and thinks his father was African American. Will finally convinces Grace to get rid of the crappy car that her uncle left her and they sell it to a nun who needs it to deliver cheesecakes. When Graces changes her mind and wants the car back, the nun demands almost ten times the amount she paid for it. Will finally makes a deal that they get the car back if they drive the nun on her errands. Karen finds out that Rosario has been cheating on her and cleaning for someone else. Karen confronts her friend that Rosario has been cleaning for and they end up playing pool: the winner gets Rosario. They both cheat and end up duking it out over Rosario. Rosario is so disgusted by the objectification that she says she doesn't want to clean for either of them anymore. Karen laments the loss of her beloved Rosie until Rosario decides to return. Will's dad, George, comes to visit New York, but it quickly becomes clear that he came to visit his mistress, not his son. Grace is horrified that Will just wants to deny the affair rather than confronting his father, and even George is surprised when Will invites him and his mistress to dinner and they spend the whole night talking about the weather. Will finally tells his father how disappointed he is. Meanwhile, Grace asks Karen about her opinion on the affair, and Karen thinks that Grace is telling her that Stanley is having an affair, so Karen enlists Jack's help in spying on her husband. Will is dating a loser named Paul, and hasn't been able to break up with him because he likes his dog, Pepper, so much. Will is in the process of trying again to break up with Paul when Paul asks Will to take Pepper for the weekend while he's out of town. Will is excited to do so, but horrified when Pepper runs away. Will tries to use Pepper's disappearance to make Paul dump him, but instead, Paul wants Will's comfort. Paul suggests they go out of town for the weekend, and Will can't say no, but when he goes to pick up Paul he finds Pepper tucked away in the bedroom. It turns out Paul uses Pepper to get guys, and pulls this trick all the time. Pepper has doggie Lo-Jack, a tracking chip in his neck, and is trained to run away. Will is finally able to walk out on Paul. Grace meets Karen's very good-looking nephew, Sumner, and sparks immediately fly. When Grace tells Karen she's interested, Karen tells her Sumner is married. Grace finds out that Karen is lying, and asks her why. Karen tells Grace that she only told her that because Sumner takes advantage of women and uses them for their money... in fact, he went to jail for it once. Grace quickly finds out that this, too, is a lie. Grace is offended, and thinks that Karen has decided that Grace isn't good enough for Sumner. When Grace confronts her employee, Karen finally admits that she actually thinks Sumner isn't good enough for Grace. Will is on the verge of kicking Grace out of his weekly poker game because his friends can't stand her playing, but she convinces him to give her one last chance. He's amazed when her game seriously improves, and she admits that she's cheating. When he is horrified, she gives him a sob story about having to win back her grandmother's turquoise jewelry, but he quickly finds out that's a lie. When he threatens to tell everyone that she's cheating, she warns him that she'll tell everyone that he was in on it. When their friend Rob later accuses Will of cheating and the two get into a violent fight over it, Grace breaks it up by admitting her wrong-doing. It turns out that the fight was just a setup to get her to confess. Karen is curious about new shoulder-enhancement surgery, but wants to see it on someone else before she goes through with it. She and Jack trick a rich cosmetic surgery-happy friend of Karen's into going through with it first. Karen is horrified when she thinks her friend died on the operating table, but is even more horrified when her friend comes out with fabulous huge shoulders and informs Karen that these were the last implants available. When Grace frets that she and Will might drift apart like their similar friends, she impulsively buys an expensive piano. She not only hopes that this communal property will keep Will from ever leaving her, but she hopes that she and Will can spend time together playing it. When Will wants to go out at night and doesn't always want to stay home and play the piano with her, Grace takes it personally. She invites all of Will's friends over to have an old-fashioned piano party, but when he'd still rather go out she loses it and finally admits her fears. He comforts her with a song about how their love will keep them together, and they agree to send the piano back. Jack gets dumped by Rocco and starts writing romance novels to "work through the pain." Karen gets incredibly turned on by reading Jack's work, and is left wanting more when Jack gets back together with Rocco. Karen pays off Rocco to dump Jack again, but Jack sees through her scam and is too angry with her to write anymore. When she offers Jack himself a pay-off as well, Jack goes back to work. Karen dumps her hated mother-in-law, Sylvia, on Will and Jack, who end up taking her to a gay club opening. She advises a morose Will that if he wants to change his life, he needs to change himself, and he uncharacteristically accepts a date with a much younger guy who works at a video store. Sylvia, when she realizes that she helped a "fag" get a date, is horrified and thinks she's going to hell. Grace rants and raves at a guy in her building, Nathan, who takes her wet laundry out of the dryer to put his own in. She finds herself giving him advice on how to get his girlfriend back, but after his attempts fail he decides to go after Grace. Grace doesn't want to give him the time of day until he kisses her, and then she agrees to one date with him. Grace and Will attend a funeral for a girl that Grace made fun of in school. Jack believes he has been nominated for a gay cabaret award. Grace hates herself for her fatal attraction to her boorish neighbor, Nathan, and keeps the relationship a secret from Will. Likewise, Will is a bit embarrassed by his dating the much younger Scott, and keeps the relationship a secret from Grace. When Karen finds out about both secrets and therefore Grace and Will realize the each has been lying to the other, the roommates agree to break up with their respective embarrassments. Will successfully sets Scott loose, but Grace can't contain herself and ends up kissing Nathan instead of dumping him. Jack loves that Val is his new number one fan, but when she starts stalking him and crawling into his bed at night he freaks out and pushes her screaming from his apartment. Later, he misses the attention again. Will finds out Grace is still dating Nathan and is disgusted. He's even more unhappy when Nathan more or less moves in with them because Grace finds out he's been living with his ex-girlfriend. Jack finally thinks he's found his father and is excited to meet him, but is devastated to find out that the man's actually been dead for five years. Will and Nathan finally become friends when Will is touched by Nathan's sensitivity in dealing with a depressed Jack. Will keeps seeing a cute guy around the neighborhood that he calls his imaginary boyfriend but is too shy to talk to. Jack finds out that he has a son that he fathered through a sperm bank when the thirteen-year-old boy shows up wanting to meet his father. Grace realizes that things are getting serious with Nathan and worries that it might ruin her friendship with Will. She plans a trip to Morocco with Will and secretly dumps Nathan. When Will finds out that Grace ruined a potentially great relationship, he insists that she stay in town with Nathan. Luckily, Will meets his imaginary boyfriend at the airport and Grace and Nathan admit their love for one another.

season 4 -
Will comes back from his trip to France early and interrupts Grace and Nathan's continuing romance. Nathan quickly starts to feel left out when Grace spends all her time with Will, but when he tries to horn in on Will and Grace's day of shopping at a sale at Barney's, he becomes grateful for Will's presence in Grace's life and realizes that there are just some things that should be left to Will. Will comes home with a fabulous pair of jeans from France that he insists are men's jeans, but everyone else insists were made for a woman. Jack worries that his son, Elliot, doesn't like him, so he takes the boy back-to-school shopping at Barney's. Elliot tries on things that Jack likes, but is hesitant to buy them, and finally admits that he was only trying them on so that Jack would like him. Rosario reminds Karen that it's their fifteenth anniversary as mistress and maid, so Karen takes Rosario to the sale at Barney's to buy her something. Karen is mystified when Rosario takes forever to decide on a pair of shoes, and finally Rosario admits that she just wanted to spend some time with Karen. Karen runs away, scared of feeling an emotion. Will pretends to be unthreatened when Kevin, a former classmate, starts working at his firm. However, the memories of Kevin forcing Will do his homework for him come rushing back when Kevin intimadates Will into writing a proposal for one of Kevin's clients. Will tries to stand up to Kevin, but is too wimpy, but gets back at Kevin by writing embarrassing things in the proposal. Grace is mortified when her perfect gift for Nathan's birthday is completely dwarfed by the motorcycle that Karen gets him. She tries to compete with Karen by getting another more expensive gift, but when all she has to give Nathan is her love, Nathan assures her that it's the best gift he's ever received. Jack's son Elliot asks a girl named Nancy to the school dance, but she says she already has a date. Jack convinces Grace to be Elliot's date and tags along as an escort. At the dance, it turns out that Nancy's date got sick, so Jack encourages Elliot to ask her to dance while Grace finds herself reliving her own high-school days as a wallflower on the bench with the other losers. Jack tries to teach Elliot to dance, but when his favorite song comes on he pushes his son to the side and takes center stage. Elliot is embarrassed, but he and Nancy bond over having gay parents. Karen has great fun at her lawyer Will's expense when she continues to capriciously summon him for bogus "emergencies" like fixing a fax machine and opening a jar of olives. But when FBI agents start investigating Karen's husband Stanley, and Karen calls Will with this real emergency, he believes she's just crying wolf again and refuses to come to her aid. When the FBI agents come to Will's office, he mocks them, thinking they're actors hired by Karen... until he sees on the news that Stanley has been arrested. After Stan is arrested for tax evasion, the gang goes to visit him in prison. Afterwards, Karen awkwardly asks Grace to stay with her in her mansion of an apartment. Grace stays to help out her friend, but after she gets a taste of the good life, Karen has a hard time getting her friend to leave, and finally has to kick her out. As Stan's attorney, Will struggles with stagefright when he babbles during a TV news interview, so Jack convinces him to polish his communication skills by attending an acting class ruled by an imperious teacher. Will has a breakthrough and becomes silky-smooth on camera. In a sneaky ploy to bum a night off from work at Barney's department store, a conniving Jack plays matchmaker. Jack knows that his geeky female supervisor has a crush on Will, while Will has a fantasy of modeling in the store's catalogue, so Jack parlays their mutual desires into a "date," even though neither knows the other's intention. Grace compares her previous sexual experience with her boyfriend Nathan's and both are concerned when Grace has had many more partners, but Nathan has had a lot more sex. Karen plays off their mutual insecurities to create a comical situation in which Grace attempts give Nathan the best sex of his life while Nathan is determined to improve his communication with Grace and not have sex at all. Nathan proposes marriage to Grace while they're having sex and she says that's not the way she wants to be proposed to. After talking to Will, Grace realizes that she does, in fact, want to marry Nathan, and decides to propose to him. But Nathan has reconsidered, and when Grace pops the question he breaks up with her, leaving her devastated. Will, Jack, and Karen war over who is more ethical. Grace wallows in bed as she grieves over losing Nathan, and Will, Jack and Karen each try, in their own way, to perk her up. The first time she ventures out to the living room, however, she hears a message on the answering machine for Nathan from a travel agent planning a trip for him and someone named Suzie to the Bahamas. Grace retreats back to bed and Karen sends Rosario in after her, but Grace just drags Rosario into watching a childhood slide show. Karen, Jack and Will try to drag Grace into a shower, but she yells at them to stop and makes them realize what's sad in their own lives. All four of them end up in Grace's bed watching a childhood slide show. Will and Grace support different candidates for city council, he the gay candidate, and she the female Jewish candidate. They both plan fund-raisers for their candidate at their apartment on the same night, and are both horrified when their candidates turn out to be bigoted conservatives. Jack is sad when Karen and Elliot don't get along, so he leaves them alone together while he goes to an audition to be a corpse on Six Feet Under. Karen accuses Elliot of being a goody-two-shoes, and he proves that he isn't by prank-calling people. Jack is pleased when he returns and Karen and Elliot are now friends. Rather than be apart on Thanksgiving Day, Will and Grace join Jack and Karen for a festive holiday motor tour of their respective dysfunctional families. Karen is miffed when she visits Stan in jail and he tells her to sleep with other men, but then she starts to explore the possibilities. Grace is horrified when Jack lets it slip to her mother that Nathan dumped her, her mother does her I Told You So dance, so Grace insults her mother by telling her she can't act. Jack takes his son Elliot to meet his stepfather who is welcoming to both stepson and stepgrandson... but Jack keeps snapping at perceived slights. Will and his brother compete over who will to ditch their mother and finally Will's brother makes their mother choose who should have to stay, and Will is set free but disturbed when his mother doesn't choose him. The gang leaves Rosario in charge of basting the turkey but she ends up eating part of it. When they get back to have dinner Rosario encourages them to go back out and resolved their family issues so she can get back to work on the turkey. Karen tells Stan she loves him and doesn't want to be with anyone else, Grace apologizes to her mother and tells her she doesn't appreciate the I Told You So, Jack and his step-father try to forge a new relationship, and Will reassures himself that he's his mother's favorite son. Rosario has finished the turkey. Will gets used as a rebound guy and decides to apologize to the guy he used as a rebound many years before. He is horrified when he finds out the two guys are a couple. Jack tries to start his workout catch phrase but he keeps getting pre-empted by a certain personal trainer at the gym. Karen encourages Grace to ask her for a loan when Grace wants to expand her business, but then turns Grace down after demanding a full presentation. Grace leaves Karen stuck when Karen gets trapped in the elevator until Karen admits that she had sound economic reasons for encouraging Grace to keep her business small. Will is dating a new guy named Robert who is a ballet dancer, but is reluctant to introduce him to Grace. Grace sneakily invites Robert over for dinner and Will is incredibly over-sensitive about Robert's flamboyant danciness and over-analyzes everything Grace says about him. Will accuses Grace of being judgmental, but quickly realizes that Robert does embarrass him and ends the relationship. Jack finagles his way into designing a window at Barney's, but he does a terrible job and his evil boss threatens him with losing his job if he doesn't fix it. Jack prays to Santa for help while Karen asks Grace even though Jack screwed Grace over to get the design job in the first place. Grace secretly redesigns Jack's window and does a great job. Jack thinks it's a Christmas miracle from Santa. Grace and Will run into Will's father's mistress, Tina, who is lamenting the state of her affair with anyone who will listen. Grace gets the idea to set up Tina with another man to get her away from Will's father, but the guy she gets to go out with Tina backs out at the last minute. Grace and Will quickly sub in their gay friend Larry, who surprisingly charms Tina. Will is excited at how well things are going until Tina starts talking about how awful his father is, at which point Will reflexively defends his dad, reminding Tina of all the reasons she loves him. Tina rejects Larry to go back to Will's dad. Jack and Karen buy a prize stallion to put out to stud, and are surprised when the horse turns out to be gay. Karen decides to put the useless horse up for auction, but at the last minute realizes she loves him and can't give him up. While visiting Stan in prison, Grace runs into a charming old crush from high school, Glen, who is doing 5 to 10 for real-estate fraud. Grace starts "dating" Glen, but is soon horrified to discover that he's two-timing her. Meanwhile, as a favor to Grace, Will has taken on Glen's appeal, and is excited to actually be litigating. When Grace breaks up with Glen and asks Will to drop the case, Will refuses, and gets Glen off, but then tells Glen to stay away from Grace. Grace ends up proud of Will's performance in court. Rosario is angry with Karen for not visiting Stan in prison enough, and can't believe it when Karen says that prison isn't that bad. Rosario bets Karen and Jack that they can't stay in her room for three days, never mind prison, and Karen takes the bet, promising to visit Stan every day if she loses. Karen and Jack suffer together for three days, and almost win the bet, but two hours away from freedom Karen realizes that if she's had this horrible a three-day stay in Rosario's room, real prison must be awful for Stan, so she loses the bet willingly and goes to visit her husband. Grace drags Will to her ex-fiance Danny's wedding. Will is annoyed by people's reaction when he tells them he's a lawyer, so he pretends to be a professional tennis player. He thinks his cover is blown when he meets another professional tennis player at the wedding, but the other guy covers for him. When they get a moment in private, the other guy admits he was just pretending too, and he actually works for the IRS. Grace gives a joking speech at the rehearsal dinner about how immature Danny is, and the next day, Danny's fiancée Sarah tells Grace she was right on the money and now Sarah doesn't want to marry Danny either. Grace goes into a long diatribe about how great Danny is to try to convince Sarah not to run, and Grace is so convincing that by the end of it she wants to marry Danny too. Sarah goes through with the ceremony, and when Danny grabs her ass and gives a thumbs up to his friends during the kiss, Grace is reminded why she left him. When Jack lets his son Elliott dye his hair blond, his mom Bonnie tells Jack she doesn't want them to spend time together anymore. Karen kidnaps Elliott from school and takes him to see Jack to cheer him up, but Jack brings Elliott back home. Jack and Bonnie argue, and Jack claims that Bonnie must not like gay people. Bonnie admits that she's gay too, but she just hasn't told Elliott yet and she might have reacted because she's jealous of how easily Jack told Elliott. She tells Jack he can see Elliott again, but warns him that she decides what color his hair will be. Karen brings Will as her date to her annual Valentine's Day party, and when her friend teases her about being alone, she claims that Will is her whore. Will is surprised when so many of Karen's female friends want to be his new "clients," and is horrified when he finds out why. Will ditches Karen and leaves her to dance the final spotlight dance alone, but at the last minute comes back to save her from embarrassment. Jack is in the final auditions for the Gay Men's chorus, and thinks that his toughest competition, Owen, is straight pretending to be gay. Grace has been lamenting her flirting skills, so Jack enlists her to help him "in" Owen. Grace gives it her best, and finally gets a very straight Owen to make out with her on the couch. Jack fails to get proof, but still tries to tell everyone at rehearsal that Owen is straight. Owen breaks down and admits that yes, he is straight, but the chorale director still lets him join the chorus, partly because he doesn't want to discriminate and partly because Owen is just so cute. Will and Grace decide they want to move to a bigger apartment, and while looking at places they fall in love with a gorgeous apartment that is way out of their price range. They decide that, to afford it, they should sublet their current apartment and gouge the renters to get enough money to afford their new place. They're excited when they find out that their friends, Rob and Ellen, who are expecting their first child, are looking to move back into New York from New Jersey. While making a film about Karen's life for her birthday, Jack finds her mother working as a cocktail waitress in a bar and decides to reunite them on her birthday. Finding their new apartment too big and rambling, Will and Grace try to trick Rob and Ellen into moving out of their old place by pretending that the Upper West Side Slasher is on the loose in their neighborhood. Unfortunately, Ellen not only doesn't fall for it, she goes into labor. With the birth of their son, Rob and Ellen decide they want to move back to New Jersey anyway, and Rob yells at Will for gouging them on the rent. Jack tries to engineer another reunion between Karen and her mother Lois, and Karen tells Lois that she still resents her for all the scams she was forced to pull as a child. Lois and Karen start to reconcile, but then Lois tells Karen there's one more con she'd like to pull, and she needs Karen to do it. Karen goes along with it, because she can't say no to her mother, and ends up at the same hospital where Ellen is giving birth, helping her mother try to scam and dying rich man out of his estate. Karen is humiliated in front of her friends when they catch her dressed up like a poor, stupid ex-cheerleader, and her mother's scam is busted anyway when the old man's daughter gets a restraining order. Will takes his parents to the Rainbow Room for their anniversary and is pleased to see how well they're getting along. Will assumes that his father has dropped his mistress, and excitedly presents his parents with their gift: a cruise for two. Will is crushed when, in a moment alone, his father asks if the cruise is fully booked or if he could bring his "buddy" Tina along, and Grace is horrified when Will's mother confides to her that she wants to bring a "buddy" of her own. Against Grace's advice, Will confronts his parents with their dual affairs, and his parents decide to separate. Will gloomily contemplates going on the cruise with Grace. Meanwhile, due to Karen's phobia of the Rainbow Room elevator, she and Jack take the stairs to the skytop restaurant while hefting the anniversary cake. In the aftermath of his parents' divorce, Will salvages a beloved garden gnome and proudly plants the childhood relic in his apartment's community garden area until Grace accidentally breaks it and blames someone else. Karen casts Jack in a mattress commercial and Jack plays straight so well he's afraid he may get type-cast and ruin his career as a gay actor. Jack is upset when Will takes Elliot to a basketball tournament in Connecticut and counsels him on what his first kiss means. Jack feels cheated out of a fatherly moment, but later on in the tournament Jack gets to help Elliot get over losing the game for his team. Meanwhile, Will becomes friends with three beefy dads who are fascinated to get to know a gay man. Grace teaches an interior design seminar at The New School and is a big boring flop. She gets her students to come back for a second day by promising them that they'll get to visit a famous person's apartment, and then tries to intimidate Karen into making her empty promise a reality. Karen tells her she'll get her into Katie Couric's apartment, but then double-crosses her and admits that she doesn't even know Katie Couric. Grace's disappointed students leave for good this time. Grace gets a little too involved when she helps plan Will's cousin's wedding in New York and starts to see herself as the bride. When she gets to the point where she's trying on the wedding dress, Will intervenes and she gets depressed, thinking she'll never get married herself. Will and Karen start becoming friends when they bond over a book they're both reading for a book club and Jack gets jealous. Will and Karen stage a fight to make Jack feel better. Will's laptop is stolen from a coffee shop and a friendly detective, Gavin, is on the case. Gavin is also a member of Jack's new gay therapy group, and he admits to the group that he's nervous about asking out guys so he makes up stories to spend time with them. He also has a big problem when people have food stuck in their teeth. Gavin tells Will they have to go undercover to a gay club to bust the gay laptop stealing ring, and Will starts to catch on that something strange is going on. When Will runs into Jack who tells him all about Gavin, he then brings Gavin home and purposely gets food stuck in his teeth to wig him out. Will gets Gavin to admit the "undercover" scheme was a ploy to go on a date, and hopes Gavin will ask him out for real, but Gavin runs away because of the stuff still in Will's teeth. Grace's crazy neighbor Val tries to be friends with Grace again, but when Grace isn't interested she tries to become a designer and steal both Grace's ideas and Grace's client. At a charity auction, Will wins a photo session with a famous photographer, Fannie Lieber, and a chance to be in her new book about families. Will brings his family, Grace, to the photo session, and they are shocked when Fannie is curt and rude to them. However, they are even more surprised when Fannie, who has been drug-free for 90 days, disappears behind a curtain for a moment and returns excitable, frantic, and horny. Will and Grace, after a mad posing session, get their picture, and Will hates the way that he looks. They demand a reshoot, but in their second picture, Grace hates the way she looks. They demand another reshoot. Eventually, the photographer accuses them of being too self-obsessed to be truly emotional. This prompts Will to jokingly ask Grace to have a baby with him. The two pause, and the photographer captures the truly conflicted emotions on their faces. Jack's new show is a magic show, but it ends up a disaster when he fights with his lovely assistant, Karen, who steals the show. Will, Grace, Karen, and Jack decide to do the things they've most wanted to do but have been afraid to attempt. Karen tries to have a conjugal visit with Stan, but Stan is busted insider trading from jail and their visit is cancelled. Karen warns Stan that she's not sure how much longer she can put up with being married a to a jail-bird, particularly now that his sentence has been lengthened. Jack tries to audition for a Broadway show, but realizes that maybe it's not his calling after all. Will tells Grace he wants to have a baby with her, but Grace thinks she might want to wait for Mr. Right. When they go see a therapist together to work things out, Grace can't help but be tempted by Will's description of what their child could be like. They decide to go for it. Will and Grace decide to use artificial insemination to get pregnant, but they misplace the sperm sample and are disappointed that they'll have to wait. They decide to try the old-fashioned way, and Karen gets them an expensive hotel room, but they can't bring themselves to actually have sex. They give artificial insemination one last try, but Grace has an accident in the park and a man on a white horse comes to her rescue. Karen is tempted when a rich and charming man comes on to her and gives her the key to his hotel room. Jack, giving up on being an actor, decides to dedicate himself to retail and his job at Barney's, and is rewarded with a promotion to floor manager. However, while celebrating in his new office, he knocks himself out and has a vision of Cher who urges him to go back to performing. Jack wakes up and races to make a voice-over audition that he was going to ignore.

season 5 -
Grace is rescued by a cute and charming Jewish doctor named Leo Markus. Leo takes Grace to the clinic on horseback and she is inseminated with Will's sperm. Will and Grace make a pact to not date other people for a while. Grace runs into Leo again and he pesters her to go out with him, but she tells him she's off the market. Leo stops by the apartment to drop off Grace's wallet that she lost and Will gets jealous, scaring off Leo and accusing Grace of dating him. It turns out Will is just feeling guilty because he kissed a guy the other night at a club. Grace finds Leo's card in her wallet with a request "from his horse" to call. Karen fools around with Lionel Banks and then decides to go for it and go all the way, but she gets a surprise when Stan shows up at her room instead. Grace takes a pregnancy test and she and Will are disappointed when it comes out negative, but plan to try again in two weeks. Leo hunts Grace down at her office and continues to pursue her. Grace pushes him away because of her promise to Will. Karen sends Rosario to break up with Lionel for her, but Rosario is seduced by him as well. Karen finally gets up the nerve to break up with Lionel herself, and then Rosario comes back for round two. Jack stalks Kevin Bacon, and then accidentally gets hired as his assistant. Jack is sad when he finds out being Kevin's assistant doesn't mean he gets to dance with him, it actually means he has to hunt down his stalker. Jack brings Will stalking with him next time, and Kevin busts them. Jack fingers Will as the stalker and runs. It turns out that Kevin is actually excited to meet his stalker, because having a stalker means his career isn't dead. Jack is horrified when he finds Kevin and Will dancing together. Grace finally gives in and calls Leo, leaving a message on his machine for him to call her. Grace has an incredible date with Leo and they share an incredible kiss. Meanwhile, Will is just getting more and more excited about having a baby. When Grace doesn't seem as excited as he is about his mother sending over his baby crib, he decides to get her a present and offer to take the pressure off. In the meantime, Grace wants to see how things with Leo will work out and wants a little more time before the next insemination, which is supposed to be tomorrow. They both get each other presents and have a heart-to-heart talk, in which they agree to wait another month before trying again. Grace, however, doesn't tell Will that Leo is the real reason she wants to wait. Will finds out about Leo through a present-returning snafu and confronts Grace. He demands that she either get inseminated tomorrow or they won't do it at all. She says then they won't do it at all, and accuses Will of not wanting her to be happy. Will tells her to move out of their apartment. Jack and Karen convince Will and Grace to attend Joe and Larry's daughter's birthday party to get the old friends in the same room together. Once there, Will and Grace each try to ensure that Joe and Larry will stay their friends, finally destroying the birthday cake in their competition. Jack and Karen lock Will and Grace in the bouncy castle, where they finally have it out, and Will admits that he hopes Leo is right for Grace, and he should probably wait to have a baby until he's found a life-partner with whom to raise it. Will and Grace reconcile. Leo convinces Will and Grace to go biking up in the Catskills and get a pumpkin for Halloween. Leo even set Will up with a friend of his, but Will is turned off when it turns out his date, Kim is less than five feet tall. Grace tries to get into the outdoorsiness, but can't fake it anymore when she is covered in mud and it starts to rain on her. Will is a grump for the entire trip, but surprisingly hits it off with Kim. Karen starts feeling guilty about her almost affair and decides to tell Stanley about it, but when she goes to talk to him, she finds out that he's having an affair. Karen leaves Stanley. Jack starts a café outside his apartment in the building hallway. Karen, who has left Stan and been cut off financially, is living with Rosario in her limo. Jack and Grace try to persuade her to move in with them, but she refuses. Finally, after enjoying Grace's pulsating shower-head, she agrees, but just then her financial worries go away and instead, Grace and Jack go with Karen to enjoy her luxurious hotel room. Will tries to help out his new boss, Mr. Stein, who admits that he's a bit crazy. Will helps Stein with the everyday tasks of running the law firm, and in return, Stein gives him perks promised to other and even fires one of the firm's favorite elderly lawyers to give Will her coveted corner office. Will's co-workers hate him, so Will tries to bolster up Stein's confidence so that Stein will be able to function on his own. Grace goes to brunch at the Plaza with Leo and they meet up with some "friends" of his. When she finds out later that he tricked her and she's actually met his parents, she regrets her earlier casual attitude. As they fight over his lying to her, he admits that he only tricked her because he loves her and he really wanted her to meet his parents. She admits she loves him too and they make up. Will gets Botox with Karen. Zandra tells Jack that he's a terrible actor, so Jack accuses Zandra of being a terrible teacher. Zandra lets him teach a class, and Jack makes acting all about "attracting". Zandra tells him he's also a terrible teacher, so he storms out of the class, actually taking two students with him. Grace and Leo run into Katie Couric in Central Park during a Today Show sweeps gimmick and end up being one of many couples that get married in a mass wedding. Will is upset when he finds out that his dream of being at Grace's wedding has been usurped, so they have a reception so that he can give his dream toast. At the reception, Grace realizes that she and Leo don't really know each other that well, and she starts to have second thoughts. When Katie Couric makes a second appearance and tells them that it turns out their marriage wasn't valid, Grace thinks maybe that's okay. Luckily, she second-guesses herself again and decides that she and Leo should get married again, and this time do it right. Will puts together a dream wedding for Grace in a very short time, but when Grace's father throws his back out and Grace asks her best friend to walk her down the aisle, Will refuses. Grace assures him that he's not going to lose her as a friend, and finally Will gives her away to Leo. After a displaced Karen is booted from her Plaza Hotel digs, a sympathetic Will agrees to let her move in with him—at least until she turns his apartment into a federal disaster zone with her exorbitant lifestyle, forcing Will to try to unload her onto Grace's shoulders. Meanwhile, Jack loses style points when he poses incognito out of fear that the "Gay Mafia" has it out for him. Grace and Leo plan on spending Christmas Eve at The Nutcracker, while Will accepts an offer to spend Christmas Eve lounging in a bathrobe with Jack and Karen at the Palace Hotel. At the last minute, Leo gets beeped and has to go into the hospital, so Grace invites Will to join her. Will, who has always loved the Nutcracker, can't say no, but when Leo shows up at the last minute he gracefully bows out so that Grace can spend Christmas Eve with her husband. Will joins Karen and Jack back at the hotel caroling the service people at the hotel, and Grace and Leo try to enjoy hot buttered rum before the show starts, but Leo gets beeped again. Grace drags Will back to the theater, but Leo shows up again just before they go inside. Grace makes the difficult decision of taking Will with her to the show, but it turns out that neither Will nor Leo really wants to watch dancing toys, so they both end up ditching her. Eventually Grace and Leo join the others at the hotel, caroling the service people. Karen goes on a date with a charming and handsome restaurant owner, Milo, but starts to get a little uneasy when he says he's going to call her and then doesn't for three days. Grace goes to give Milo a piece of her mind, and is shocked when he admits to being a playboy and says that he lied to Karen to make her feel better, but she's too old for him. Grace tries to give Karen the news gently. Jack talks Will into joining a gay soccer team, under the assumption that it will be like a "gay bar on astroturf", but when the team turns out to be serious about the game, Will decides to quit because he's terrible at soccer. Jack is upset when Elliot decides to quit his own soccer team because he's so bad at the game, so Will decides to stick with it to be a role model for Elliot. Elliot quits his team anyway, and Will actually has to get off the bench and play when one of his teammates is injured during a game. In a total fluke, while trying to run away from the ball, Will slips and, while falling, kicks the ball backwards into the goal, scoring the winning point for his team. Grace moves into Leo's apartment in Brooklyn and meets a friendly neighbor, Julie. Julie is a massage therapist, and when she gives Grace a free massage, Grace is concerned when she massages a little further south than usual. Grace gets Karen to hire Julie to see if that's a normal part of Julie's massage, and when she finds out that it isn't, she asks Julie about it. Julie assures Grace that it's perfectly normal for girlfriends to be physically friendly with each other, and that's all it was, friendly. Grace is reassured, but thrown off-guard when Julie surprises her again during a hug. Karen sets up Will with her newly out-of-the-closet cousin Barry. Jack tries to fight Will for the opportunity to date Barry, until he sees the man. While Karen encourages the relationship, Will tries to let Barry down easily. Jack tells Will that he should mentor Barry, and teach him how to be a proper gay man. Will and Jack begin their Barry project in earnest, particularly after Karen gives them money to back it. Will works on the mind while Jack works on the body. Will encourages Barry to try to pick someone up at a gay bar, remembering his success the first time he did it. Barry is shot down, and Jack admits that he paid the guy that Will asked out his first time. Barry thinks Jack and Will are too shallow, and since they're still alone, he doesn't think they can teach him anything, but finally he admits that having any kind of help is better than no help at all. Leo tells Grace that he has to make a last-minute month-long trip to Africa for Doctors Without Borders. On the way to the airport, Grace picks a fight, and after Leo goes to get on his plane she regrets it. Grace buys a last-minute plane ticket and gets on Leo's plane, but just as the plane is taking off she finds out that he went home to make up with her. Will and Grace worry that they've lost their mojo (or in their case, their homojo) when they don't seem to have the connection that they used to. Their situation becomes critical when it looks like they might lose at game night with their friends. They have a serious talk and vow to work harder at communicating about the little, trivial things that are so important in their lives, and they get it together just in time to pull a win. Karen has to fight for her queer when Jack becomes entranced by the new woman in Stan's life, a British ex-stripper named Lorraine. Grace hosts girls' night at her apartment, looking forward to Leo returning soon, but Leo calls and says that he'll be staying longer than he originally planned. Grace says that's okay, and asks all her female friends, except Karen, if that was the right thing to do. All the other unhappy women say that sounds fine, but Karen says Grace should tell Leo she's upset, but then stomps out, angry that Grace didn't want her opinion. Grace calls Leo and tells him that she's upset and they need to make these decisions together, and Karen comes back and she and Grace reconcile. Jack runs into his old babysitter, Sissy, and hires her to be his babysitter again. Will is disgusted by the strange relationship between Jack and Sissy, and urges Jack to end things, but what finally convinces Jack to get rid of Sissy is when he finds out how much she costs. Will and Jack's transformation of Karen's schlubby cousin Barry is complete, and the whole gang gussies up to attend the gay gala of the year. Will suddenly realizes that he's attracted to Barry, but just before he gets up the nerve to ask him out, clueless Jack beats him to the punch. Karen spars with her old "friend", Beverly Leslie, who is out for blood now that Karen has been dumped by Stan. Will and Jack, now both infatuated with Barry, make Barry choose between them, and Barry chooses Will. Will has a week of great dates with Barry, and finally gets Jack to forgive him by telling Jack that he looks older when he's angry. Will asks Barry to be exclusive, but Barry says he wants to play the field for a while since he just came out. Karen impersonates a maid when a hot maintenance man at her hotel mistakes her for one. They start a passionate love affair, and Karen finally admits that she's not really a maid, she's actually rich. Karen is excited when her poor maintenance man says he can still love her even though she's not poor like he is, but when she finds out that he doesn't drink she calls the whole thing off. A lovesick Will mourns the loss of Barry and forms a lonely hearts club with Karen and his crazy boss, Mr. Stein. Unfortunately, the club comes to a screeching halt when Karen and Mr. Stein hook up. Grace tries to make a sexy videotape for Leo, but turns to Jack for acting help when she realizes that she's more silly than sexy. Jack finds that the best solution is to tape Grace in the shower when she doesn't know about it so she acts natural. For Grace's birthday, Will flies in Leo as a surprise, but when Leo arrives a day early Will tries to hide him away to preserve the surprise for the day of Grace's actual birthday. Leo gets fed up and goes back to his apartment to freshen up, but he runs into Grace there and they have a happy reunion. When Grace finds out what Will went through to surprise her, she tells Leo that they have to pretend they didn't see each other, but when Leo sees Will, he can't keep his mouth shut. Will decides that he and Leo shouldn't tell Grace that Will knows that she's not going to be surprised, but when Karen and Jack get wind of what's going on, they decide to take Grace to an arcade. Karen decides to get a taste of "real life" and moves in with a woman named Liz. She and Liz get along fabulously until they go out clubbing and set their sights on the same guy. Liz tries to kick Karen out of the apartment, but Karen realizes that she actually owns the whole building, so she kicks Liz out instead. Will falls off his clogs and sprains his ankles. When Will starts enjoying his painkillers a little too much, Grace and Jack stage an intervention. When Karen finds out that Will is representing Stan in the divorce, she hires her own hotshot attorney, Jason Towne. Will worries about Karen's judgment when Jason turns out to be a young snot-nosed kid that doesn't know pro bono from a fidelity clause. Will tries to help Jason, and then advises Karen to get a new lawyer, but when Karen confronts Jason it turns out that he's not as bumbling as he seemed, that it was all an act to make Will slip up. Jack brings in a new client for Grace, his latest boyfriend, Cam. Not only is Cam rich, but Grace loves his taste in home decor, and when Cam dumps Jack the next day, Grace is loath to give into Jack's demands and drop Cam as a client. Grace goes to tell Cam she can't work for him anymore, but Cam talks her into remodeling his enormous country house instead. Jack busts them and Grace finally quits entirely, valuing her friendship with Jack too much to betray him. Then, of course, Jack gets back together with Cam. As the divorce proceedings continue, Karen suddenly finds out that Stan has died. Karen and all her friends attend the funeral, as does Stan's mistress Lorraine, who was under him at the time of his death and was trapped under his body for two days. A number of people speak fondly of Stan at his funeral, but everyone is really just waiting for the reading of the will. Rosario finds out that she gets $10 million if she works for Karen for another 20 years. Grace gets a painting of Karen. Apparently, Stan thought Will and Jack were a couple, and leaves them $20,000 to get married. Finally, Karen finds out that she gets the bulk of Stan's estate, and Lorraine is left with nothing. Leo gets invited to Guatemala to help set up a new Doctors Without Borders clinic, and asks Grace to come with him. Grace happily accepts his offer, even though she really doesn't know where Guatemala is. Grace gets more and more depressed about going to Guatemala with Leo, especially when Will and Jack plan to accompany Karen on her yacht to the Caribbean Sea to scatter Stan's ashes. Leo tells Grace she can go on the yacht instead of to a third-world country with him, and she celebrates until she sees the hot blonde doctor that will be going with Leo. On the yacht after Leo's departure, Grace convinces herself that he would never cheat on her, but becomes more concerned when she discovers a letter from hot doctor Danielle to her husband saying that she wants him. Grace orders the yacht to Guatemala. Karen, while scattering Stan's ashes, discovers that his mistress Lorraine has stowed away on the boat. The two women actually start to get along, until Lorraine asks Karen for some of Stan's money. In the fight that ensues, Lorraine pushes Karen overboard and Rosario jumps in after her to save her. Karen and Rosario end up being rescued by a Russian barge that is delivering thousands of cases of Stolichnaya vodka. Will and Jack thoroughly enjoy their tropical vacation, and also enjoy a few too many tropical drinks. They are both horrified when they wake up in the same bed.

season 6 -
Karen and Rosario get back to the yacht on a stolen Jet Ski, and Karen tries to weasel out of her promise to let Rosario take one Friday off of work a month because Rosario saved her life. Grace freaks out about the romantic letter to her husband from another doctor, but when Leo has to come back to the U.S. (because he left his passport in the bag that Grace had), he assures her she's the only woman he's interested in. Leo decides to give up Doctors Without Borders so he can be with Grace. Jack and Will wake up naked in bed together and aren't sure what happened. Each decides the other must be romantically interested, and each tries to let the other down easily. Luckily, Karen has video surveillance in every room on the boat, and she confirms that nothing happened between the drunk and naked duo. Leo invites his pretty ex-girlfriend, Diane, to dinner at his and Grace's apartment, and Grace rounds out the guest list with Will, Karen and Jack for the dinner party. Grace has all jealousy firmly under control, and even gets along with Diane, until she finds out that Diane also happens to be the only woman Will has ever slept with. The night degenerates from there when Grace has a jealous fit about Will, Leo wonders why Grace isn't jealous about his relationship with Diane, and Diane admits that not only was Will better in bed than Leo, but Will gave her the only orgasm she's ever had and she still carries a torch for him. Some peace is made when Will explains to Grace that Diane meant nothing to him, and that's exactly why he was able to sleep with her and not with Grace, his best friend. Jack and a lecherous Karen comfort a weepy Diane and give her Lorraine's small dog that they found in Karen's closet. When Grace and Leo go to play tennis at a posh country club with Karen, Grace finds out that Karen actually doesn't like Leo. Grace is bothered by this, but Leo convinces her that it doesn't matter, because he doesn't really like Karen and her opinion doesn't matter to him. Just as Grace is becoming used to not caring what Karen thinks, Leo does an about-face and starts trying to prove to Karen how likeable he is. Grace tells Karen that if she doesn't like Leo, then they probably won't be spending as much time together anymore, and Karen is so concerned about losing Grace as a friend that she promises she will always pretend to like Leo—just like she does Will. Will and Jack go to visit Will's mother, Marilyn, after her divorce and find her moping around in the dark drinking wine and not bathing. They take her to see Mamma Mia on Broadway and cheer her up, but then she dreads going back home. Jack has the great idea of having Marilyn move in with Will for a while, and even though Will thinks it's a terrible idea, he can't say no when he sees how much his mom perks up at the idea. Jack gets a one-line part in an off-Broadway play starring James Earl Jones, but when the director likes Jack's delivery better than James's, James Earl Jones finds himself studying in Jack's acting class. Grace trails after a woman and her trainer at the gym so that she can make use of the trainer without having to pay for it. Will and his mother are both sick of living together, but neither wants to say it to the other. Finally, they admit their feelings, and Marilyn decides to move back home that night, but in the process of moving she twists her ankle and Will finds himself having to care for his wheelchair-bound mother for a few more weeks. Leo gets an offer to set up a clinic in Cambodia, and he is itching to go, but realizes that if he left he would make Grace miserable. While Grace is sick in bed, Will takes Leo out on the town to remind him of how great New York is, but Will's New York is not Leo's New York, and Leo is relieved when he finally talks Will into going to a Rangers hockey game. Leo still wants to go to Cambodia, and it's Will who ends up distressed when Leo reports that he is going to Cambodia... and Grace is going with him. Karen coaches Jack to prepare for a gay spelling bee, but when Jack is one of the final two contestants, he gets angry with Karen when she tries to help him cheat. Luckily, Jack wins on his own anyway. Will is frustrated by still having to take care of his mother who is in a wheelchair, but when he meets a cute guy in the park who is also wheeling his infirm mother around, he forces Marilyn to stay even when she's able to get around on her own. Will finally goes out on a date with the cute stranger from the park, but it turns out that he's a big freak that can't be away from his mother for even an evening. Karen hunts down an L. Finster at a local hotel, and goes there to confront her rival, Lorraine. Instead, Karen meets Lorraine's dapper father, Lyle, who immediately takes a liking to Karen and convinces her to make out with him even though she claims to hate him. Karen has to get a physical, but she ends up with an extremely unorthodox doctor. Grace calls from yet another fast-food restaurant in Cambodia. Jack meets a cute male nurse and enrolls in nursing school. After he demands that Karen and Will support his dream and pay his tuition, he drops out, deciding to be a surfer instead. Will and Karen go to the nursing school to get the tuition back, and find out that nursing was something that Jack was actually good at. Jack's friends convince him to seriously give nursing a try. Grace comes back from Cambodia, ostensibly for her mother's 50th birthday party, but she later admits to Will that she's back for good. Her being in Cambodia with Leo wasn't working out, and there's something wrong with their marriage. She's going to stay in New York and wait for him to be done with his assignment in Cambodia. Will offers to let her move in with him again, and she happily accepts. Jack has a new tough teacher in nursing school, and when she makes Jack sad, Karen threatens her, guaranteeing Jack an A. However, when Jack starts coasting and skipping classes, he soon realizes that he actually misses his classes and studying. Everyone goes out to a restaurant, but when they can't get their table for 5, because Will's date hasn't shown up, Grace grabs a stranger from the bar so that their "entire party" is there and they can get seated. Will meets a woman at the bar who thinks he's cute, so he flirts with her to make himself feel better after getting stood-up. Meanwhile, it turns out that the stranger Grace grabbed is actually a guy she randomly made out with in a bar in her early '20s, and she flirts with him in order to make herself feel better about her crumbling marriage. Will is horrified by what Grace is doing, and tells her companion that she's married. Grace is equally horrified by what Will is doing, and tells his companion that he's gay. Grace and Will's dates leave together. Karen runs into her old friend/arch-nemesis, Candice Bergen, and they continue their trend of playing practical jokes on each other. At one point, they team up, and play a practical joke on Jack, making him think that Candice needs the Heimlich maneuver which he recently learned in nursing school. Will is excited to be first in line for Barry Manilow tickets, and asks Grace to hold his place while he runs across the street to use the bathroom. Grace is shocked to see her mother, who cancelled their annual Hanukkah shopping trip, having dinner at a nearby restaurant with Jack. Grace calls Karen and gets her to hold Will's place in line while she confronts her mother. Meanwhile, Will snubs a guy who is hitting on him only to later find out that he is Barry Manilow's tour manager, and can get him backstage to meet the man himself. Will does some serious ass-kissing, and promises to go on a date with the guy in Philadelphia, in order to meet his idol. Grace realizes that she actually does want to spend time with her mother, and is jealous that her mother is choosing to spend time with Jack instead. Karen realizes she likes Barry Manilow's music. Grace's screw-up sister Janet comes to town, and when she decides to crash at Will and Grace's apartment and sponge off them while she gets her celebrity jewelry line going, Grace finally yells at her and tells her to get a real job and her own apartment. Grace is amazed when, just a few weeks later, Janet has a studio apartment, a job at Ann Taylor, a new look, and cooks a fabulous dinner for Grace and her friends. Unlike Will and Jack, Grace can't seem to be happy for her sister, and finally she admits that she likes having screw-up sisters, because then she gets to be the normal one. Janet tells Grace that this was all Will's doing, and Will admits that he thought Grace wanted a normal sister, so he tried to make Janet normal. Grace is touched that Will would go through so much trouble for her, and is relieved to hear that Janet got fired from her job at Ann Taylor because she was drunk on the job. Meanwhile, Lyle Finster hunts down Karen, and tells her he wants her, but she blows him off. However, when Lorraine shows up and tells Karen to keep her dirty paws off her father, Karen runs straight to Lyle's bed and arranges for Lorraine to find them in a compromising position. Lyle tells Karen that he's in love with her, so Karen admits that she slept with him just to annoy Lorraine. Karen tells Lyle that she has fallen for him as well, but Lyle feels used and kicks Karen out of his hotel room. Will goes to an art opening and meets a handsome older man, Alan, who is a rich plastic surgeon. He is surprised when Alan buys him one of the paintings at the opening, and then as they begin to spend more time together, Alan buys him more and more extravagant gifts, including a horse and a Western outfit to go with it. Grace points out to Will that he has a sugar daddy, while Jack bemoans his lack of a sugar daddy. Will confronts Alan, who plays hurt and makes Will feel bad for assuming the worst, but Will later finds Alan with a brand new boy toy at another art opening. Grace discovers a great Asian noodle place near her office, but when she drops her take-out and they won't replace it for free, she decides to boycott the place and get all her friends to boycott it too. Luckily, Jack and Karen ignore her, and she finally realizes that the noodles are just too good to stay away. Will has a new client, Stuart, that meets Jack and wants to be set up with him, so Will bribes Jack into going out with him. When Stuart starts including Jack in the negotiations to sell his company, and follows Jack's ridiculous advice, Will blurts out that he bribed Jack. Both Jack and Stuart end up hurt, so Will figures out a way to get them back together. Grace takes Karen up to Vermont with her to tend to Leo's cabin where the pipes have frozen. When they get into bed, they find thousands of dollars stashed beneath the mattress. Grace, horrified that Leo has been hiding all this money from her, decides to go out and spend it on frivolous things. Grace is later horrified when she realizes that she was in the wrong cabin, and she just spent an elderly couple's life savings. Will takes a cooking class, and gets depressed when he's the only single person in it. Luckily, a really hot guy named Adam shows up and not only pairs up with Will for cooking, but is also immediately attracted to Will and wants to take him home. Will is excited until he is led to believe that Jack might have hired Adam who is actually a prostitute. Will tells off Adam who leaves, hurt, and then Will finds out that Jack didn't hire him. Will chases after Adam, but it turns out that it was actually the cooking teacher, Ann, who hired Adam for Will, thinking Will was pathetic and alone. Karen's mother Lois moves to New York to be closer to Karen and asks to Grace to decorate her apartment. Grace does so, on a tight budget, because Lois doesn't want to take any money from Karen. Grace and Karen work hard to make the apartment beautiful with as little money as possible, and they do so. Lois is pleased that she has a place in which her daughter can come visit her, but when she gets an offer to sell the apartment for $100,000 more than she paid for it, she takes the money and runs to Japan. Will and Grace realize that that wouldn't be a bad business plan. While seeing patients as a student nurse, Jack runs into his old acting teacher Zandra who is preparing to move into the Actors' Retirement Home. Will and Grace, who want to be the apartment flippers who care, begin by buying Zandra's apartment and re-doing it. When Zandra sees it, she decides she wants it back, and Jack tries to guilt Will and Grace into giving it back. However, when Stuart sees the apartment, he proposes that he buy it and he and Jack move into it, and suddenly Jack forgets all about Zandra. Lyle Finster finally forgives Karen for using him, and he moves into her luxurious apartment. When Lorraine shows up penniless at their doorstep, Lyle convinces Karen to let Lorraine move in with them. Karen is quickly disgusted by the way Lyle always coddles Lorraine and always gives into her. Jack and Stuart prepare to settle into their new apartment, but quickly realize that they're moving too fast and aren't ready to feel so settled—and old. Will and Grace encourage their indecision, having just received a huge offer on the apartment. The flippers who care feel they've learned a lesson in caring when Jack and Stuart decide not to take the apartment, and the huge offer is withdrawn at the same time. They decide to sell the place back to Zandra, but when the huge offer is re-issued, Will doesn't hesitate to boot Zandra again. Lyle finally disciplines Lorraine a little, and she yells at him and moves out. Lyle blames Karen for driving a wedge between him and his daughter, and leaves her. Lorraine comes and finds Karen and tells her how miserable Lyle is. Lorraine and Karen make their peace, and Lyle and Karen happily reunite. Everyone decides to move back into Karen's apartment together, and Lyle proposes marriage to Karen, which she happily accepts. With their new apartment-flipping business, Will and Grace find themselves going head to head with the infamous flipping dykes of the East Side, Deirdre and Monet. To defeat them, they decide to divide and conquer, and Will goes after the weak one, Monet, who is clearly attracted to him. Their plan fails, however, when Deirdre makes a move on Grace. Karen worries about not having Stan's blessing for her new marriage to Lyle, but can't get John Edward to put her in touch with Stan's spirit. Jack tries to impersonate Stan's spirit and tell Karen that she has his blessing, but Karen doesn't fall for it. Luckily, Karen does fall for it when Rosario does it. Jack and Grace go to the movies, and Jack is horrified to see Stuart there with a hot young guy. Jack makes a scene in the theater and stomps out, but later finds out that Stuart was seeing a movie with his son. Stuart apologizes to Jack for not telling him about his son, and Jack apologizes for not telling Stuart about his son either. Will attempts to teach Karen how to drive, but they quickly get pulled over and given a ticket. When Will sees that the cop forgot to sign the ticket, he decides to fight it in court. In court, Will and cop who wrote the ticket realize that they have mutual friends who have been trying to set them up for years, so instead of fighting over the ticket they decide to go out on a date Friday night. Grace advises Will to not be so needy in his burgeoning relationship with Vince, and instead play it cool. Will takes her advice, but plays it so cool that he turns off Vince, who isn't into stupid relationship games. Luckily, Will realizes that he screwed up and apologizes to Vince, and Vince is very forgiving. Karen is horrified when she finds out both Friends and Frasier are having their series finales this year. She and Jack lament the loss of their favorite shows, and wonder what they're going to talk about now that they're over. Both of them freak out when they run into Bebe Neuwirth, who they both call Lilith, in their favorite coffee shop. Will finally introduces Vince to Grace by having them both over for dinner, but when Grace leaves in a rush before dinner has even been served, Will can't stop stressing that she doesn't like his new boyfriend. When Will drags Vince over to Grace's apartment to ask her what's wrong, she admits that she actually likes Vince very much, she was just saddened seeing the two of them so happy together when her relationship with Leo is such a mess. Karen tells Jack that they won't be able to spend much time together after she gets married and that he should be ready to move on. However, when Karen sees Jack auditioning replacement straight female friends, she gets jealous and promises him that she'll find time for him. Will's dad's mistress, Tina, comes to Will concerned that his dad, George, is seeing someone else. Will investigates, and finds out that his father and mother have started sleeping together again. Will tells Tina that his dad is seeing someone else, and she should move on. Will's mother comes over and tells him that sex with his father isn't as much fun now that they're not sneaking around. At the same time, Tina comes over because she found out that it was Will's mom that George was sleeping with. Will tells Tina to get over it, and tells his mom to just be with his dad and be happy about it, but after they leave Will's apartment, the two women agree to share George instead. Elliot tries out for the cheerleading squad at school just to get some of Jack's attention. Jack's nursing school graduation is a day earlier that he expected, and he hasn't yet prepared his speech that he gets to give because he was voted most popular student. Will, who is depressed that a play he wrote in college isn't as good as he thought it would be, takes on the task of ghostwriting the speech for Jack. Will writes a beautiful and moving speech about following your dreams, and as Jack starts to read it at graduation, he realizes that nursing isn't his dream and he still wants to be an actor. Lyle comes up with the idea of skipping the picturesque fall wedding, and instead getting married in Vegas. Karen warms up the private jet and takes Will and Jack to Las Vegas, Nevada with her for her wedding. Karen finds herself compromising more and more to Lyle's wishes, but Jack assures her that marriage needs compromise. Karen meets Lyle's strangely affectionate brother, Marion. Leo shows up from Cambodia, and breaks the news that Grace hurt her back in New York and won't be able to make it. Will is confused as to why Leo doesn't seem that broken up about Grace not being there, and doesn't jump at the chance to borrow Karen's jet and go see his wife. Leo finally admits to Will that he kissed someone else while he was in Cambodia. Karen bumps into Jennifer Lopez in the hotel bathroom and gets her sing at the wedding because Jennifer used to be friends with Rosario. Karen and Lyle get married, but Karen is furious because the one thing she insisted on, the music when she walked down the aisle, Lyle changed without consulting her. Karen swallows her rage as Lyle eloquently apologizes for not honoring her wishes about the music. Will encourages Leo to talk to Grace and tell her the truth about kissing another woman. Rosario leads the wedding guests in the chicken dance. Jennifer Lopez shows up to perform, but one of her backup dancers twists his ankle so Jack fills in. Lyle gives an eloquent speech about how much Karen has given up for him, and says he's lucky to have found a woman who is "happy to mortgage her entire personal identity" just for him. Karen realizes she's not happy that way, and decides she wants a divorce. Leo, after talking to Grace on the phone, tells Will that Grace never wants to see him again. Will is confused why Grace would overreact so badly to one kiss, but then Leo admits he actually slept with the other woman. Will tells Leo that he's on his own. Jack is ecstatic when he gets an offer to go on tour with Jennifer Lopez.

season 7 -
Grace, in her fury, raids Leo's apartment when he's at work during the day. Leo finally comes over to Will's to talk to Grace, and even though she yells at him and gives him his ring back, she realizes that she's miserable without him. Against Will's advice, she decides to give Leo a second chance, but after one awkward night out to dinner with their friends, Grace realizes she can't make it work and admits that her marriage is completely over. Jack, who is now good friends with Jennifer Lopez, makes the mistake of giving her a song written by Karen at the exact wrong time. Jennifer fires Jack, but because she still likes him as a friend, gets him a job dancing for Janet Jackson. Jack must compete in a dance-off so he can be a back-up singer for Janet Jackson. Meanwhile, Will has to decide whether to go out with his boyfriend or help Grace cope with her failed marriage. Grace wanders into an AA meeting following a woman carrying donuts and runs into her old crazy friend Val. For the free food and the free therapy, Grace lets everyone, including Val, believe that she has a drinking problem. Luckily, Karen, horrified at the thought of AA, exposes Grace to her meeting. Will and Jack attend a focus group for a new gay cable network, OutTV. Will is offended when no one will listen to his brilliant show ideas, while Jack, with his ridiculous ideas (like naked Jeopardy) gets hired as the VP of New Programming. Will and Grace meet a new guy in their building, Ned, and Will tries to be friendly, while Grace ignores him and is outright rude. Grace scolds Will for being nice, saying they don't want to get to know any random new people in their building. Later, Grace is in the elevator with Ned, and he mentions that he thinks she's rude. To prove that she's not, Grace invites Ned over for cocktails, and she and Will proceed to have one of the most boring nights of their lives. However, Will can't contain himself, and asks Ned over for dinner on Friday. Ned cancels dinner at the last minute, because his brother got into a car accident and he has to go to the hospital, but when Will and Grace hear music coming from Ned's apartment upstairs, they know they've been lied to. They go upstairs to confront Ned, who tells them that he heard all the terrible things they said about him while he was in the bathroom, and they hurt his feelings. Will and Grace apologize, and sincerely invite Ned over for dinner again. Ned says he's busy having tea with friends, but Will and Grace are welcome to join them. Will and Grace are slightly horrified when they come into Ned's apartment and join a tea party full of stuffed animals. Jack is feeling intimidated by his coworkers with marketing degrees and work experience, and finds himself being a yes-man and just trying to agree with everyone else's opinion on everything. He even goes so far as to throw his Cher doll in the trash when one of his coworkers scoffs at the stereotype that all gay men love Cher. Karen reminds Jack that while his coworkers may have fancy degrees and work experience, while they were stuck in school Jack was watching TV, and he knows TV. Jack is uplifted, and decides to stand up for himself, gaining the respect of his boss. His boss even suggests that Jack should do a documentary on Cher. Will has a bad history with birthdays, but he's really hoping that this one, now that he has a boyfriend, will be better. Vince decides to give Will a key to his apartment for his birthday, but Grace talks him out of it, thinking it will be cheap. Will is disappointed when he gets a wallet from Vince, and the rest of his party goes to hell when Karen is depressed that it's also Stan's birthday, and she and Jack decide to celebrate Stan instead. When Grace sees how sad Will is, she convinces Vince to give Will the key after all, but Will doesn't want it if Vince had to be talked into it. Finally, Grace has to admit that it was all her fault for talking Vince out of it in the first place, and then Will happily accepts his birthday present from his boyfriend. Grace's latest design job has her interior decorating for a young and very happy newlywed couple. She tries to keep her cool, but once they announce that they're pregnant and need to decorate a nursery, she just walks out. Karen completes the whole thing for her, and does a very good job. Grace thanks Karen, but then when the young couple compliment Grace on the design, she takes all the credit. Karen is nice and quits being Grace's assistant. Will and Jack get caught up in the cause of saving a gay bookstore that's going out of business because its rent is too high. When Will realizes that a beautiful new gym was planned for the space, he regrets saving the store, because he has been wanting a new gym in his neighborhood. Jack scolds Will for being so fickle, and Will comes around, donating the last of the money needed to save the book store. However, when the owner says that they've now just saved the book store for one more month, both Jack and Will decide that whole thing is a lost cause. Will and Grace have Vince and his best friend Nadine over for dinner. Nadine is so sweet that she makes Grace nuts, so Grace prods Nadine to admit something that she doesn't like about her best friend, Vince. Nadine explodes that she doesn't like Will, and storms out of the apartment. Will is concerned that this could break up him and Vince, but makes Grace promise not to interfere any more than she already has. Grace promises, but immediately breaks it when she calls Nadine and meets up with her for coffee. She tell Nadine that there is no chance she and Vince will ever get together, because Vince is gay, and she should just give up and stop trying to drive away her best friend's boyfriends. Nadine realizes Grace is right, and apologizes to Vince. Will realizes Grace helped, but doesn't know how. In the meantime, Karen takes a new job working as Jack's assistant, but they have so much fun in the office together that he can't get any work done and has to fire her. Karen goes back to work for Grace, ignoring the fact that she quit and pretending that she was just out at the store for 10 minutes. As Grace's dreaded wedding anniversary approaches, Will sets her up on a date with a great guy named Alan. Grace has a wonderful time, but when she gets home, there is a garbled message from Leo on her answering machine. Grace thinks that Leo wants to meet on the roof of the Peninsula Hotel for their anniversary like they originally planned, and she can't stop thinking about it. To get her mind off of it, Will plans a getaway for the two of them in the Berkshires. Grace says she's psyched to get out of the city and get Leo off her mind, but she takes the answering machine with her so she can listen the message some more. In the meantime, Karen and Jack set each other up on dates, but they both do a horrible job. Jack sets up Karen with her own gardener, while Karen sets up Jack with a closeted married man. They decide that no one is good enough for either of them, and they should just be a couple themselves and have sex on the side with other people. Up in the Berkshires, Will finds the answering machine in Grace's bag, and Grace admits that she's still torn about going to the Peninsula Hotel. Will convinces Grace that she shouldn't think about it anymore, but then worries that he pressured her into the decision and someday she'll wonder if Leo was there. Will runs back to the city to check the Peninsula Hotel for Leo, and Grace tracks him there. Grace says she appreciates Will taking care of her, but she knows she made the right decision. Jack finds Peter, the guy he remembers from the Cocoa Devil commercials who always said, "It's sinfully delicious." Jack puts Peter in an Out TV commercial, but Peter refuses to say his old line, finding it degrading. Jack gets desperate when Peter runs away, but Karen finds the Cocoa Devil and convinces him, with a story from her own past, that it's okay to be famous for something stupid. As Thanksgiving approaches, and Will and Vince plan to bring together their respective "families" for the event, Vince warns Will that his mother never likes his boyfriends. To get a jump on Vince's mom liking him, Will takes her out shopping, but accidentally causes her to break her toe while trying on some very high heels. To make it up to her, Will decides to cook her usual big Italian Thanksgiving dinner, even though she spends the entire time trying to put him down. Vince's sister, Ro, admits to Jack that she's a lesbian and wants to break up with her fiancé. Jack tells Ro she should come out at Thanksgiving dinner, but Will, wanting everything to be perfect, convinces her to wait. Karen and Grace, who have both been single for a while and haven't had any recent sex, find themselves fighting over Vince's hot cousin Sal—who they later find out is only 16 years old. Vince constantly feels put down by his dad, even though the slights are only imagined. Finally, as dinner is served and Will is giving the toast, he can't take Vince's mom's bad-mouthing anymore, so he lets her have it, outing Ro and embarrassing Grace and Karen at the same time. He prepares to leave, but Vince's mom realizes how much Will loves her son, and asks him to stay. While at a holiday tea at Will's mother's house, Grace breaks one of Marilyn's treasured Lladro figurines, and hides the evidence under the couch. Will counsels Grace not to say anything, but Marilyn figures it out and lays a trap for Grace's conscience. Karen's step-daughter Olivia shows up for Christmas, and Karen bribes Jack to take care of her. Karen becomes jealous when Jack has a good time with Olivia and her friends, so she tries to hang out with the teens as well and embarrasses Olivia. Jack engineers a holiday reunion between the two women, who bond over how they used to tease Olivia's brother and how much they loved Stan. Walker Inc. is the subject of a hostile takeover by a man named Scott Woolley, who is taking revenge for Karen using her boobs to win school president back in high school. Woolley get the board of directors to vote him in as CEO, but when he steps out of the room, Karen reminds all the directors of all the dirt that she has on them, and they vote her back into power. Grace and Jack see Vince at a grocery store while he's supposed to be at work, and initially think that he might be cheating on Will. The truth, however, is that Vince finally screwed up too many times as a cop, and was fired from the force. And he's not doing a very good job of keeping his new job at the grocery store either. Will announces that he's up for partner at his firm and Vince admits that he got fired. Will's boss, Margot, has a dinner party for him and the other two partner candidates. Margot also invites Grace to dinner, saying that she has someone she wants to set up with Grace, but the someone turns out to be her own pathetic husband who just wants to be spanked. Vince goes to dinner as Will's date, but is even more depressed because he just got fired from another job as a security guard at a jewelry store. Will is torn between kissing Margot's ass to get the job as partner, and caring for his obviously depressed boyfriend. When he finally tells Margot he has to take Vince home, Margot gives him the job as partner anyway. At home, Vince says he doesn't want to be the guy that brings Will down, and they mutually decide to "take a break," even though Will realizes they're probably breaking up. Rosario is sick, and ends up in the hospital after having to have her tonsils out. Karen insists that Rosario is faking it, until she thinks Rosario has died, when she admits that she just didn't want to face the idea of perhaps losing her maid/friend. Jack takes Will out dancing to help him get over his breakup with Vince, but Will is good when Jack ignores him and ends up going home with some other guy. Jack tries hard to make it up to Will, and tricks him into meeting him at a café where he promises to give him his full attention. Will is impressed when Patti Lupone, Jack's Broadway idol, shows up and sits next to them, and Jack manages to ignore her so that he can talk to Will. Scott Woolley makes a ridiculous second attempt to ruin Karen's life by trying to trick Grace into firing her, but Karen turns the tables on his silly ruse. Grace comforts a depressed Woolley, who realizes that he's actually in love with Karen and should be trying to date her instead of ruin her. Karen goes to her country club Valentine's Day Ball to meet a blind date that she met online. She is surprised to find out that her blind date is Scott Woolley, but she agrees to hang out with him when he saves her from the ridicule of her nemesis, Beverley Leslie. When Karen realizes what serious feelings Woolley has for her, however, she quickly cuts him loose so as not to hurt him any more. When Will and Jack hear Beverley Leslie declare that two men will never dance together at this country club, they take it as a personal challenge, and encourage a middle-aged pair of lesbians to do the same. Grace, working alone in her office on Valentine's Day and suffering through a party being thrown upstairs, meets Nick, a handsome errant party guest with whom she shares a Valentine kiss. Jack meets a sexy birdwatcher named Aaron because Aaron is obsessed with a bird on Karen's balcony. Jack is attracted by the cute wholesome nerd, but then Karen accidentally kills off the bird, and bribes Aaron with cash to keep him happy. Jack sees a darker side to Aaron... but still thinks he's really cute. Grace goes on a date with Nick and is worried that she'll sleep with him too quickly. She begs Will to come along and protect her from herself, but he ends up just sweating to death at a table in the restaurant near the fireplace. Will takes on the task of firing Karen's pastry chef, but when he goes to give him the sack, they end up in the sack instead. Will is infatuated with his new sexy pastry boy, but when he finds out that his hottie is sleeping with both Karen and Rosario as well, he is quickly disillusioned. Grace's new guy, Nick, gives her a script he wrote to read and then pass along to Jack at OutTV. Grace is scared to read it, in case she doesn't like it, but she passes it along to Jack anyway. Jack meets with Nick, and admits to Nick that he didn't read it. When Nick gets nice, Jack passes the buck by saying that Grace didn't read it either. Nick is angry with Grace, and doesn't understand why she was afraid to read the script. Grace finally reads it, and even though she hates it, and tells Nick that much, she's pleased that she can separate the bad script from the guy who wrote it and still really like Nick. In the meantime, Jack also finally reads the script, and OutTV (with some drastic changes) decides to make it into a movie of the week. Both Grace and Nick are sad when it turns out that Nick will have to spend three months in Vancouver for the shooting of his movie. Jack and Will buy a house in upstate New York, in a town called Middleborough that Jack swears is an up-and-coming gay getaway. When the two find out that Jack actually read about Middleborough, New Hampshire, they decide to abandon their new house, but the townspeople are actually excited to have gays moving in, because that will make property values go up and create more restaurants and shops in town. Jack and Will have to sneak away to avoid the banana bread and quiche gifts that the townspeople keep forcing upon them, as well as the school band that keeps marching by playing "We Are Family". Grace agrees to babysit Ellen's three kids, and Karen offers to help out, but Grace scoffs at Karen's ability to care for children. Karen's feelings are hurt and she's mad at Grace, but when Ellen decides that Grace isn't responsible enough to watch her kids without Will there, Karen comes to Grace's defense. Will convinces Grace to see his tough therapist, Dr. Georgia Keller, and is surprised when the two women not only hit it off, but Georgia offers to put Grace in her new book. Will decides to compete with Grace to get into the book, and the two friends end up telling Georgia that she can only use one of them. Georgia talks to Will and Grace together, and they both admit that they know that their relationship is unhealthy. Georgia assures them that they're just fine, and that they actually balance each other out, which is very comforting to them. In the meantime, Jack convinces Karen to get glasses, but when she tries them on for the first time and looks in the mirror, she thinks she looks old and freaks out. Jack convinces her to wear them, and Rosario assures her she looks great. Karen, who can finally see, decides that Rosario has been doing a terrible job of cleaning her apartment. Karen drives Grace to her parents' house for Grace's dad's birthday, but Grace is horrified when her mother tells her that she's leaving her alone with her dad. Grace tries to talk to her dad and work on their relationship, but finally gets fed up with always being the butt of her father's jokes. Her father apologizes and tries to be the more serious and caring dad she wants, but can't help laughing at his daughter when she falls through a chair. Luckily, Grace is happy that her dad is at least trying to take an interest in her life instead of just her pitfalls. In the meantime, Karen entertains herself with Grace's dad's creepy friend, a dry-cleaner named Burt Wolfe. Back in the city, Jack sets up Will on a blind date—with an actual blind man. When Will's date feels his face and is bummed that he always gets set up with ugly guys because he's blind, Will gets all bent out of shape, which is when Jack runs out and admits that the whole date was being filmed for OutTV's version of Punk'd, called Pinked. Jack desperately tries to get Will to sign the release so that they can air his episode of Pinked, but Will refuses, saying that he's already self-conscious enough about his looks. To get Will to sign the release, Jack admits he's self-conscious about his looks too, and shows Will that he's wearing a girdle. That's when Will tells Jack that he's now been Pinked too. Grace finds out from Will's mother that Will only left her $1,400 in his will, and wonders why she isn't worth more to him since he's pretty rich now. He admits that when he wrote that will, 15 years ago, it was all the money he had, and he hasn't been able to re-write it since then. Every time he looks at all the stuff he has, he just worries that he hasn't really accomplished anything or done good in the world, just become a rich corporate lawyer. Will quits his job. Jack finds out that another teacher has taken over his old acting class and is teaching the McFarland method. Karen uses a connection to get the new teacher a cool acting job so that Jack can have his class back, but once Jack starts teaching again he realizes he didn't really want to do it, and it feels like a step backwards now that he's a cable television executive. Will tries to be a writer, but he's really bad at it. A strange man named Malcolm pretends to be interested in Will's writing, but really, it's all just a mysterious ploy to get Will to be a lawyer again. Malcolm tells Will that his connections at the New Yorker didn't like his writing, but offers him a job as a lawyer running a charitable foundation for kids. Will happily accepts. An ex-boyfriend from college named Tom reappears in Grace's life and asks her to design his new hotel. She's excited to see him, until she realizes that he's now married, but that doesn't stop him from making a move on her. She stops him right away, not interested in being "the other woman". An obnoxious former child star is signed to host Jack's new talk show. He and Jack have a blow-out fight that is caught on camera, and the star quits, but Jack's boss says that Jack looks good on camera, so Jack gets the hosting job. Beverley Leslie threatens to sue Karen if she doesn't apologize for calling him a homosexual in public, but Karen just tricks the little man into outing himself. Grace realizes that she has to quit her new job as the designer of Tom's hotel when things continue to be awkward between them. Tom visits Grace's office to apologize, but they end up in a lip-lock. Will starts his new job, and things get stranger and stranger until he demands that Malcolm tell him what's going on. Malcolm gives in and shows Will who his real boss is: Karen's not-so-dead husband Stanley. Just before Jack starts filming his new talk show, Jack Talk, his boss, Jamie, sees him and Karen fooling around together and decides that Karen would make a great co-host. Jack feels like Karen is stealing his spotlight and tells her to butt out, but he later apologizes. Karen says it's okay, this can be just his thing, and when Jamie finds out that Karen isn't, actually, a drag queen, he says he's not interested in her anyway.

season 8 -
Grace tries to tell Tom that she doesn't want to hook up with a married man, but he continues to pursue her. After talking with Jack, Grace decides to throw caution to the wind, but when Jack realizes what he accidentally talked Grace into, he quickly talks her out of it. Jack is missing an eyebrow from a fire at the premiere of his talk show. Will tells Grace about Stan being alive, and the news quickly gets out. Malcolm asks out Karen, and Will is horrified, so to stop the date he tells Karen that Stan is alive. At first, Karen doesn't believe him, but then when Rosario admits that she's been reporting to Stan on Karen for over a year, Karen fires Rosario and goes out with Malcolm anyway, saying that Stan may not be dead, but he's dead to her. Karen kicks out Rosario for not telling her about Stan being alive, and Will makes it his mission to emotionally heal Karen. He gets Karen to let some of her emotions out, but when all her bad memories start coming back to haunt her, she lashes out and scratches some of Will's open wounds to bring him down with her. Will and Karen end up drunk together, and decide together to put back up their emotional walls. Karen, however, decides to hang onto how hurt she's been by Stanley, while Will decides to figure out why he threw away a great boyfriend and a burgeoning career. Grace accidentally appears on Jack's talk show, and due to bad editing, it looks like she says that she hates all gay men. When gays all over New York start yelling at her and throwing things at her, she forces Jack to let her back on the show so that she can set the story straight. When Jack learns that Will never learned to swim, Jack insists that he teach Will how. However, Will doesn't really trust Jack, so he secretly signs up with a real instructor. When Jack finds out, he's incredibly hurt, and can't believe Will doesn't trust him with this when he trusted him with coming out of the closet. Will realizes Jack is right, and cancels his lesson with the instructor, entrusting his safety back with his friend. Karen sets up Grace on a blind date with one of Malcolm's friends. Grace is put off when she finds out the guy is a piano tuner that lives on a landfill in Staten Island, but when Karen calls Grace a snob, Grace determines to give the guy a chance. She ends up really liking the guy, but when he hears her sing, it turns out he's the snob and he ends their date early. After Stanley secretly talks to Jack, Jack tells Karen that he thinks she belongs with Stanley, but Karen says that she's happy with Malcolm. Jack goes to tell Stanley the bad news, but is interrupted by Malcolm who want to talk to Stanley himself. Malcolm later tells Karen that Stanley gave them his blessing to be together, and Karen, guess as hell, confronts Stanley, hurt that he would give her up without a fight. She says that there's nothing he can say to get her back, but all he has to do is say one thing and she goes running back into his arms. Will starts delivering food to the elderly homebound, and brings one older gay man, Clyde, home with him on the same night that Grace tries to celebrate the 10th anniversary of game night. Will forces Grace to play Celebrity with Clyde, who is totally useless, and Grace finally blows up at Will for ruining game night. Will admits that he worries that he's going to end up like Clyde when he's an old lonely gay man, but then Clyde tells everyone he's actually not gay, and he used to be married to a doctor but then she cheated on him so he left her. Everyone realizes that Clyde is actually Grace's future. Jack hooks up with another wanna-be celebrity gay man, Baby Glenn, whose 15 minutes involved falling down a hole and being stuck there for 3 days when he was 12 years old. Jack and Baby Glenn both go up for auction at Will's charity auction and carnival, and while Baby Glenn actually gets bought for $1,100, no one bids on Jack. Will tries hard to pretend that Jack sold for $1,500, but Jack knows that it was Will doing the bidding. Will bucks up his old friend though, saying that it was worth every penny, and Jack really will be famous someday. Karen, who is back with Stanley, is still dating Malcolm, because she doesn't want to break his heart. When Grace lets it slip to Malcolm that Karen is back with Stanley, Karen and Malcolm break up, and Grace is left to pick up the pieces of Malcolm, agreeing to be his date to Will's carnival. When Grace can't take the freaky Malcolm anymore, Karen comes to the rescue and gets back together with Malcolm, but just as she's about to dump him again, he gets called for 2-year mission in Sri Lanka and breaks up with her. While en route to London, Will and Grace spot Grace's ex-husband Leo on their flight. Will charms a pair of gay flight attendants, and ends up working as a flight attendant himself, to smuggle Grace into first class to talk to Leo. Grace and Leo start out awkward, but end up remembering why they fell in love, and they have sex on the plane. Grace is okay with this being closure, but Leo tries to make it something more. Grace is tempted, but once they're back on the ground, she remembers why their marriage didn't work in the first place, and she bids Leo a sad goodbye. Back in New York, Jack tries to reunite Karen and Rosario, but he has to face off with Karen's new British maid who is determined not to lose her new job. Jack gets Rosario and Karen back together, but has to face off against the violent new maid to do it. Jack decides to find a new apartment, and Will becomes oddly obsessed with the plight of two gay penguins at the Central Park Zoo that are going to be separated. Luckily, Jack realizes that Will is confusing the penguins' plight with his own, and decides not to move, donating his apartment money to the zoo so that the penguins don't have to be separated. Karen and Grace attend the funeral of Beverley Leslie's wife, Crystal, and Grace can't resist trying on a custom couture gown that used to belong to the late woman. When trying to help Grace out of the gown, Karen gets her own outfit stuck in Grace's zipper, and so they spend the ceremony stuck together with a blanket covering Grace's dress. Of course, Beverley Leslie busts them, and then gets his own outfit stuck in the zipper of the dress while trying to get Grace out of it. Grace finds it impossible to put up with her mother Bobbi's constant nitpicking, so Jack takes it upon himself to help her because, according to him, no one knows how to be a good daughter better than a gay son. Jack subjects her to a barrage of Bobbi-esque insults until Grace finally learns what her mother really means underneath her harsh words. Meanwhile, Will's first case at the Coalition for Justice is about tenants' rights, and the slumlord turns out to be none other than Karen. While spending the holidays at Will's mother Marilyn's house, Grace gets cozy with Will's brother and old flame Sam. Sam's adopted daughter finds a fan in Karen, who is intrigued by the little girl. Meanwhile, Jack helps Will's nephew organize and perform a Christmas show, which Marilyn is thrilled about. Will is silently fuming, however, as Marilyn is much more tolerant of the young boy than she ever was of her own son. The "Sound of Music Sing-Along" has come to town and no one is more excited than Grace. She plans to, with Will, attend the musical in character by dressing up in costumes. The night turns into a disaster when she ends up babysitting a group of children and Will accidentally goes to the wrong theater, then is detained further by James, a handsome man he meets. Meanwhile, Karen and Jack try to flee when Karen gets in trouble with the theater's manager, who blocks off the exits, trapping everyone inside and forcing them to plot their escape. All of New York's high society has been invited to Karen's birthday party – but the affair goes downhill when Will, Grace and Jack embarrass themselves and wind up crammed together in Karen's bathroom with the birthday girl. Grace is confused when Will adamantly insists that she turn down a job offer from his former boss Margot, who has asked Grace to redecorate the law firm. When she takes the job after telling Will that she wouldn't, Grace learns some startling news that he has been hiding from her. Meanwhile, Jack discovers Karen's softer side when he finally sees what's inside the "forbidden room" at the Walker mansion. Will and Grace dread a dinner date with married friends Rob and Ellen who they assume will announce Ellen is pregnant yet again – but when the couple reveals that they are separated and loving it, Grace gets depressed. She's quickly distracted however when Will's cop ex-boyfriend, Vince, approaches their table as their server. Ignoring Rob and Ellen's big news, Will and Grace discuss how Vince must have gone off the deep end and quit the force after splitting with Will, and Vince's request to switch table assignments seems to confirm their thoughts. Meanwhile, Jack decides he needs to spice up "JackTalk" by helping his fan, Tommy Shields, come out of the closet. Jack and Karen set up a bowling alley meeting with Tommy when Karen is recruited to join a woman's league game as an emergency fill-in. Jack, Will, Karen, and a star struck Grace travel to Los Angeles to support Elliot as he is visiting colleges. Coincidentally, Will runs into James while in LA, but to his surprise James is Canadian and in jeopardy of being deported. After spending a perfect weekend together, Will and James find that they don't have to say good-bye to each other again when Grace makes a special proposal. The big day has finally arrived – Grace and James are getting ready for their green card wedding. To Grace's dismay, Karen takes it upon herself to ignore her wish for a low-key wedding ceremony and decides to arrange a huge affair instead including hiring Hall & Oates to perform "Maneater" at the ceremony. However, despite Karen's plans and Grace getting sick before the vows, the wedding goes well, with James singing to Will during the ceremony. The next day, Grace discovers she's pregnant from her earlier encounter with Leo. A nervous but optimistic Grace decides to tell Leo she is pregnant with his child, but when she finally works up enough courage to actually meet with him, she decides not to when she discovers that he's engaged. Meanwhile, Will is settling in comfortably with James until he reveals a side of himself unknown to Will. And as Jack attempts to document every moment of Grace's pregnancy for his talk show, Karen sulks alone, jealous over the good fortunes of her friends. An ecstatic Jack coerces Will into going out with him to a gay cowboy bar to meet his new boyfriend Travis. Will soon discovers that Travis is not as perfect as he seems and steps up to defend Jack's honor, which eventually leads to a bar fight. In order to show Karen the positives of multiculturalism, she hires an incompetent Iranian assistant. After a large corporation takes over OutTV, Jack's talk show "JackTalk" is completely revamped. An immediate change comes when the new conservative owners hire Amber-Louise as "JackTalk"'s new co-host. While Jack is deciding whether or not he'll stand up to his new bosses, Karen goes baby shopping. After seeing Grace so happy about her pregnancy, Karen decides she wants a baby of her own and offers to pay a make-up lady, Cricket, to carry one for her. After losing his job as the host of "JackTalk," Jack vows never to return to acting. An unrelenting Karen, however, will not let Jack give up on his passion and decides to do whatever it takes to get Jack to an audition. Meanwhile, Grace accompanies Will to dinner at his parents' home, but a simple dinner soon turns into a showdown between Will and his father when his dad decides to give Grace's unborn child Will's cherished baby blanket. Friends and family gather for the funeral of Will's father. During the reception everyone shares with Will fond last memories of his father, while Will's last memory of his father is not as pleasant. As he tries to come to terms with their last fight, Marilyn helps him realize the changes he must make in his life. Will's ex-boyfriend Vince also attends the funeral service. Meanwhile, Grace attempts to comfort the grieving younger members of the family and begins to doubt her ability to be a good mother. Will and Grace begin attending childbirth classes in preparation for the baby, but as Will and Vince take another chance at their relationship together, Grace starts to doubt whether Will is up for raising a child with her. Meanwhile, Karen looks to Jack for comfort as her marriage with Stan hits a bumpy road but finds that Jack is a little preoccupied with his new television show. Just as Will and Grace are settling into the idea of raising the baby together, Will's boyfriend Vince surprises him with an announcement that will ultimately lead Will to choose between his commitment to Grace and his relationship with Vince. Meanwhile, Karen shocks everyone when she announces that she has a sister, Gin, who was injured as a child during a game of Twister. Jack, on the other hand, is comforted by a man after a devastating discovery when his new show "The Badge" premieres. Grace and Leo have a baby girl, and Will and Vince have a baby boy. Grace has a weird dream about the gang's future. Karen's arch-enemy Beverly Leslie makes an offer to Jack that changes his life. In the second part of the series finale, Will and Grace have a falling out that lasts for years. They eventually meet up when their children meet in college (who eventually get married) and make up.

season 9 -
After both going through recent divorces, Will and Grace end up once again living together in Will's apartment. The gang ends up at the White House, where Grace has landed a job through Karen to redecorate the Oval Office and Will has brought Jack to meet the gay Congressman to whom he has been flirtatiously writing. Will and Jack are faced with the harsh reality that they are much older than they used to be when they begin to date younger guys. Grace comes to the realization that she needs Karen more than she thought she did. After having a breast biopsy, Grace is reunited with her ex-husband, Leo, when he's brought in as her emergency contact. While Jack teaches theater to kids at the community center, Karen helps a girl become a young woman. When Jack gets reunited with his son, Elliot, he learns he has a grandson, Skip, who happens to be gay. While Will and Jack try to bail Skip out of reform camp, Karen helps Grace get her sexuality back. Grace tries for her biggest job yet: decorating a string of boutique hotels for an obnoxious mogul. Meanwhile, Will is surprised at his reaction to making Senior Partner, Beverley Leslie discloses a secret to Karen, and Jack fights for his half of a winning lottery ticket. After Rosario passes away from a heart attack, Karen decides to throw the party for her that she never had: a quinceañera. While Jack struggles to know how to be there for Karen, Lorraine Finster makes a surprise return to show her support. Will upsets Grace when he leases the office space next to Grace's office without her permission. On Christmas Eve, Will, Grace, Jack, and Karen stop at a historical museum so Grace can use the restroom; however, the museum requires them to take the tour before she's allowed to use it. All four find themselves on a more "interactive" tour than they anticipated. Will and Grace take a bread-making class and both end up falling for their celebrity teacher, Jackson Boudreaux. Jack and Karen struggle to get a catchy jingle out of their heads. Will and Grace learn that Larry has a major crush on Will and Jack and Karen fight off the craziness of Val, who's after Karen's friendship. Vince, Will's ex-boyfriend, invites him to his wedding, prompting Will to reevaluate their relationship and why it ended. A cop exploring his sexuality falls in love with Jack, but his wife is none the wiser. Karen goes on a scavenger hunt. While Will and Grace venture into their next business move selling bed linens on QVC, Jack's new love interest outs himself to his wife. Grace is shocked when she realizes she slept with three men (the grandfather, the father, and the son) from the same family. Will and Karen spy on her staff at the mansion and produce a telenovela of them. Will and Grace go to Ellen's niece's baby shower. While Jack is shooting scenes with Jennifer Lopez for Shades of Blue, Karen is put in charge of the kids in his acting class and unexpectedly bonds with one of the girls. Grace and Karen cause commotion at a bakery that refuses to make a cake for the President. Jack cautions Will about moving too fast in his new relationship with his ex, Michael. Will and Grace go to Schenectady to celebrate Bobbi Adler's birthday. When Jack gets dumped by Drew, he goes to Karen for support, only to find that she's cheating on Stan with Malcolm. Will and Grace end up in an awkward position after Grace invites Will's mom, Marilyn, over as revenge for Will inviting Martin, Grace's dad, to move in with them. While Malcolm makes Karen choose between him and Stan, Jack gets over Drew by romancing a flight attendant, Estéfan. A double proposal ensues.

season 10 - 

Grace runs for office, campaigning for president of the New York Society of Interior Designers, where she meets Noah, the West Side Curmudgeon. Karen asks Will for legal advice when she learns an Italian doctor is "knocking off her knockers." Jack's FaceTime call to his fiancé's family goes awry after using a facial numbing cream for an upcoming surgery. Karen disappears after seeking help from her friends but, with Grace distracted with her campaign, Will starting a new career teaching law, and Jack avoiding marriage, none of them realize why she has left until Malcolm reveals that he told Stan of their affair. Karen is then served divorce papers. Grace wants the apartment to herself to have sex with Noah, so she sends Will along with Jack to Texas to support Skip at his talent competition. Meanwhile, Karen runs into Beverly Leslie at her sponsored portion of the border wall. In a walk down memory lane, Will and Grace embarrassingly read their college love letters, which teaches Grace an important lesson. Jack, now a certified psychic, helps Karen sort through memories of Stan and channels Rosario to reignite her faith in love. Grace takes a road trip with her dad to Schenectady. At a roadside diner, her father's cheeky remarks to a waitress finally lead to her opening up about her story involving one of her old bosses, her father's friend. Meanwhile, Will and Karen engage in a lip-sync battle to decide who will be Jack's best man. Karen helps Jack with his return to theater and his production of Gaybraham Twinkin' while Grace tries to help Will bond with Noah, who confesses he has a 12-year old daughter. Will convinces Grace that her boyfriend, Noah, is not in the wrong by refusing to let her meet his daughter, Katie. When Grace goes to apologize to Noah, she unintentionally meets Katie. Meanwhile, Will's mom, Marilyn, visits after the death of her beloved dog and becomes upset when she doesn't get the emotional support she expects from her son and Jack gets into an argument with his rec center boss, Theo. During Karen's divorce settlement negotiations, Grace and Karen are forced to revisit an old acquaintance. Meanwhile, by mimicking Jack's behavior, Will lands a date with celebrity news anchor McCoy Whitman. Will, Jack, and Karen discover there is more to chocolate milk than just sugar and dairy. Grace struggles to accept a relationship between her sister, Janet, and a new client. Will invites his boss over for dinner in an attempt to gain a full-time teaching position. When things go awry, Will and Grace find themselves in a very awkward position. Meanwhile, Jack tries to control a rift between Karen and his fiancé, Estefan. Will puts together a "Mock Trial," in which Karen and her estranged step-daughter, Olivia, play the plaintiff and defendant. After an embarrassing double wardrobe malfunction, Grace and Jack decide to go on a diet. Will finds out that office dating can come with strings attached. Grace unwillingly mediates the reunion between Karen and Malcolm. Meanwhile, Jack rediscovers his love of acting and learns a valuable lesson. It's election night for the presidency of The New York Society of Interior Design. Grace makes quite an impression on the voters after a run-in with her former nemesis, Val. In desperate need of a date to Jack's wedding, Will attempts to rekindle a relationship with McCoy Whitman. It is Valentine's Day and, in Grace's desperate attempt to buy Noah a gift, she assaults a Supreme Court Judge. Karen meets her favourite author and decides to take matters into her own hands once she discovers the ending isn't what she'd hoped. Jack realises that lying does not pay off after he tries to convince Estefan that Will has a crush on him. Martin and Marilyn join Will and Grace for dinner. Martin gets rushed to hospital and needs a blood transfusion, but refuses to accept one from Will. Grace is incensed, but Will lets it lie because he is tired of fighting for his rights and dignity. When Marilyn finds out, she chastises Martin for his behavior and Will for not standing up for himelf. Will explains to Martin the state of gay men's health; Martin apologizes and tells Will he loves him. Marilyn allows Grace to call her "mom," conditionally. Meanwhile, Karen is paying for Jack's wedding, but uses that to monopolize the planning. When she refuses a tacky unicorn-themed dessert station, and also alters his play, Jack disinvites her from the wedding and refuses her financial support. After Karen tells Jack he is like a little sister to her, they reconcile; he accepts her offer to pay for the wedding, including the dessert station. When both of their boyfriends ask to move in, Will and Grace use each other as an excuse to get out of it. A snowstorm traps Karen at the office and Jack in an elevator, where he reunites with old flame Drew and tests his commitment to monogamy. Jack realizes he lost 13 gold coins he is supposed to give Estefan at their wedding to avoid a curse. Will is concerned that Grace is the only one compromising in her relationship with Noah. Karen shows up at a dinner party with her new date, Nikki. Jack and Estefan's romantic wedding in Spain takes a detour when their flight is cancelled, forcing them to get married at the airport by their friend Miss Coco. McCoy's big job offer in London has Will worried about engaging in a long-distance relationship. While dealing with doubts about her current relationship, Grace meets a charming guy at the airport who inspires her to make an impulsive decision. Meanwhile, advice from Smitty makes Karen reconsider her commitment to Nikki and her own sexual orientation.

season 11 - 

Grace returns from her travels a new woman, but her elation is short-lived when she receives life-changing news; Karen teaches Will how to be better at phone sex; Jack has a yard sale to discreetly get rid of Estefan's cuckoo clock. When Grace admits she's not sure who's the father of her baby, Karen orchestrates a "Mamma Mia" situation with the potential baby daddies; Will worries what will happen if he has a straight son and enlists Jack to help him prepare. Will discovers a way to finally get back at Jack for years of mocking his hairline; Grace is determined to prove to Mrs. Timmer she's strong enough to handle being a single mother; Karen squares off against Stan's brother in a poker game. Will and Grace fight over whose process of having a baby is more difficult; Jack helps Karen prove that she'll be a competent owner of her new baseball team, but Karen realizes that an old acquaintance may be the help she really needs. In the aftermath of Will and McCoy breaking up, Grace and Jack hire the Grief Panda to help Will process his pain; with Karen completely occupied with her baseball team, Grace believes that she has to fire Karen in order to set her free. Committed to becoming a father on his own, Will meets a potential surrogate, to gain entry into AnnieCon, Grace pretends to be a formerly-famous Annie. Grace and her neighbor give their romance another shot, but an embarrassing incident puts Grace's relationship and dignity in jeopardy; Will cuts Jack off financially to get him to grow up. When Larry warns Will and Grace about the entry process into the elite school they want their kids to go to, they set out to prove that their child would be the better candidate; Jack creates problems between Karen and her booty buddy. Will and Grace decide to intervene when they discover Grace's niece is dating a bisexual man; Jack gets permission from his husband to sleep with his hall pass; Karen struggles to adapt when her assistant books them on an economy flight. Marilyn goes behind Grace's back to fix her up with a beagle-breeding couple interested in adopting Grace's baby; Will helps Karen deal with a PR nightmare; Jack and Estefan go to extreme lengths to get rid of a mouse. Grace and her neighbor, James, give their relationship one more shot, but when James invites Grace to his job at the aquarium, she endangers his job and a species; Jack takes Will to an unexpected place to blow off steam -- church. Karen introduces Will and Grace to the new love of her life. When Miss Coco Peru tells Jack that he's closing down his bar for good, Estefan encourages Jack to become its new owner. Will and Grace race to save Karen when they think she is in danger after her new boyfriend takes her to a cabin in the woods; Jack makes up a story to a reporter in order to keep his new bar relevant after its previous owner steps down. Jack helps Karen sneak into the manse to retrieve her ring, but they're shocked to find it on the hand of Stan's new girlfriend; while hosting Will's surrogate, Will and Grace become the old folks they swore they'd never become. Will ropes Dr. DiLorenzo into going on a fake date so he can spy on his surrogate; Grace struggles with popping her gender reveal balloon; Karen is torn between celebrating her team's championship and helping Jack with a Broadway audition. Will claims living with Grace is like Ricky living with Lucy; when Karen and Jack hear this, they each claim that they are the Lucy of the group; Grace, Karen and Jack each imagine themselves as Lucy, with Will as the Ricky to all of them. Karen celebrates her baseball team's championship; Will and Grace go to an open house, which leads to a conversation about their future living arrangement; Jack has to decide if he wants to stay in the city to pursue his dreams. Will is determined to not reminisce about his life in the city or his ex; Grace has false alarms of going into labor; Karen tries to get closure with her ex-husband; Jack's dream of taking a bow on a Broadway stage becomes a possibility.