Will & Grace: Season 2

1999 · 24 episodes · ★ 7.8

What Season 2 of Will & Grace

Grace has moved out and Jack has gotten married. But, since Grace is just across the hallway and Jack is married to Rosario, expect more hysterical situations, sharper comedy, and more of the bitchiest one-liners.

24episodes

Sep 21, 1999premiered

May 23, 2000latest episode

8.8 hrtotal runtime

Season 2 Episodes

2x01 Guess Who's Not Coming to Dinner
Sep 21, 1999 · 22 min
Despite her moving out (to across the hall), Will still feels that Grace clings to him, so she asserts her independence by having a dinner party without him. Meanwhile, to keep the INS at bay, Jack is forced to move in with Rosario.
Directing: James Burrows · Writers: Max Mutchnick, David Kohan · Cast: Leigh-Allyn Baker, Shelley Morrison, Tom Gallop
2x02 Election
Sep 28, 1999 · 22 min
When Grace feels that Will is abusing his power as president of the tenant's association, she runs against him. Karen tries to buy back Jack's forgiveness when she lets his beloved bird, Guapo, fly out the window.
Directing: James Burrows · Writing: Adam Barr · Starring: Shelley Morrison, Shirley Prestia, Lou Cutell, Lyn Alicia Henderson
2x03 Das Boob
Nov 2, 1999 · 22 min
A deceiving, but flattering, newspaper photo makes Grace look more "endowed" than she really is and gains her the attention of a former high school heartthrob who was never one to keep abreast of her before. Jack is destroyed to learn that Will had a fling with Walter, Jack's ex-boyfriend.
Directing: James Burrows · Writer: Jhoni Marchinko · Starring: Scott Patterson, Anthony DeSantis
2x04 Whose Mom Is It Anyway?
Nov 9, 1999 · 22 min
Grace is jealous when her mother stops match making for her, and instead sets Will up. Jack must convince an INS agent (who he dated once) that he and Rosario are happily married.
Directing: James Burrows · Writing: Alex Herschlag · Starring: Peter Paige, Shelley Morrison, Debbie Reynolds, Andy Comeau
2x05 Polk Defeats Truman
Nov 16, 1999 · 22 min
When his work for Harlin takes up all his time, Will drops all his other legal clients; a decision that later comes up to bite. Meanwhile Grace tries to teach Karen how to live on a budget.
Directing: James Burrows · Writing: Jeff Greenstein · Starring: Elaine Bromka, Gary Grubbs
2x06 To Serve and Disinfect
Nov 23, 1999 · 22 min
An unemployed Will agrees to serve as one of Jack's cater-waiters, until he learns that he'll be catering for American Bar Association. Grace discovers Karen's darkest secret: she once made a porn video.
Directing: James Burrows · Writer: Katie Palmer · Cast: Terry Kiser, Brian Palermo, Kim Robillard, Alex Boling
2x07 Homo for the Holidays
Nov 25, 1999 · 22 min
Will and Grace are shocked to learn that Jack never told his mother he was gay and encourage him to open up to her at Thanksgiving. The evening brings a revelation for Jack as well: his father isn't who he thinks it is.
Directing: James Burrows · Writing: Alex Herschlag · Starring: Veronica Cartwright
2x08 Terms of Employment
Nov 30, 1999 · 22 min
Grace looks to Will for representation when a hotshot lawyer doesn't pay her for a consulting assignment, but he ends up making Will a job offer. Meanwhile, Jack and Karen turn a training film set into an adult entertainment experience.
Directing: James Burrows · Writers: David Kohan, Max Mutchnick · Starring: Jo Marie Payton, Gregory Hines, Aaron Lustig, Bob Clendenin
2x09 I Never Promised You an Olive Garden Mid-Season Finale
Dec 14, 1999 · 22 min
Tired of Rob and Ellen's low-rent taste in dining, Will and Grace start hanging with a pair of hip downtowners they meet at a sushi joint. But as the new pals paint the town, Rob and Ellen see red when they catch their best friends lying to avoid plans to dine at their favorite eatery: a coupon-crazy Italian chain in Secaucus. Meanwhile, Jack's inner child gets a little pick-me-up when he joins Karen at a PTA meeting at her kid's school.
Directing: James Burrows · Writers: Jon Kinnally, Tracy Poust · Starring: Penn Badgley, Leigh-Allyn Baker, Steve Valentine, Tamlyn Tomita
2x10 Tea and a Total Lack of Sympathy
Jan 11, 2000 · 22 min
When they appear on their favorite TV show, Antiques on the Road, Grace can't wait to dress down the guests who are ever hopeful that their tchotchkes are worth a fortune, while Jack just wants to undress the show's attractive appraiser, Porcelain Paul. But then it's all business when they realize that their junky, thrift-store teapot is actually valued at $30,000. Meanwhile, Will's new boss makes the reluctant lawyer kiss up to Karen in hopes of landing her hubby as a client.
Directing: James Burrows · Writers: Jon Kinnally, Tracy Poust · Starring: Jo Marie Payton, Gregory Hines, David St. James, Connie Sawyer
2x11 Seeds of Discontent
Jan 25, 2000 · 22 min
Grace is excited to meet Will's best friend from high school until she learns that the woman has made a request: to be implanted with Will's sperm. Now Grace has to confront Will about Will being her ""backup.""
Directing: James Burrows · Writing: Jhoni Marchinko · Starring: Megyn Price, Laura Kightlinger
2x12 He's Come Undone
Feb 8, 2000 · 22 min
Erotic dreams about Grace send Will to a therapist, who seems more interested in Grace. Meanwhile Jack and Karen clash over her treatment of Rosario.
Directing: James Burrows · Writing: Adam Barr · Starring: Markus Flanagan, Shelley Morrison
2x13 Oh Dad, Poor Dad, He's Kept Me in the Closet and I'm So Sad
Feb 15, 2000 · 22 min
Will's ideal relationship with his loving father sours when his dad prepares to accept an award at his company's dinner banquet but tries to dissuade his son from attending because he's told everyone that Will is married to Grace. Meanwhile, Karen's private detective finds Jack's biological father.
Directing: James Burrows · Writer: Katie Palmer · Starring: Perry King, Sydney Pollack, Mimi Cozzens, Joe Ochman
2x14 Acting Out
Feb 22, 2000 · 22 min
Will and Jack appear on Today to protest NBC for cutting a gay kiss out of an eagerly-waited sitcom episode. Will is frustrated with Jack on how much he wanted to see that kiss and kisses him. Elsewhere, Grace confides in Karen about dumping her boyfriend.
Directing: James Burrows · Writers: David Kohan, Max Mutchnick · Starring: Jo Marie Payton, Corey Parker, Jeff Blumenkrantz, Al Roker
2x15 Advise and Resent
Feb 29, 2000 · 22 min
When Will is set up on a blind date by his boss, he has internal debates on whether or not to go. Of course, Jack gives Will advice on how to be a good blind date. Meanwhile, Grace continues to struggle with her wimpy boyfriend Josh as Karen doles out some typically un-wanted advice.
Directing: James Burrows · Writers: Jon Kinnally, Tracy Poust · Starring: Jo Marie Payton, Corey Parker, Gregory Hines, Michael E. Rodgers
2x16 Hey La, Hey La, My Ex-Boyfriend's Back
Mar 14, 2000 · 22 min
Will thinks that he has another chance with Michael, his old boyfriend and Grace's new client. Meanwhile, Karen tries taking her ""career"" more seriously and asks Grace for greater responsibilities.
Directing: James Burrows · Writer: Jeff Greenstein · Starring: Chris Potter, Christian Zimmerman
2x17 The Hospital Show
Mar 28, 2000 · 22 min
While on a blind date, Will finds out that Karen's husband Stan has had a heart attack and rushes to the hospital to be with the gang. Will, Jack, Grace, and Rosario all speculate on who Karen will turn to for her inevitable emotional breakdown. After all, who will pay the bills if Stan dies?
Directing: James Burrows · Writer: Adam Barr · Starring: Reggie Hayes, Dan Bucatinsky, Shelley Morrison, Jennifer Elise Cox
2x18 Sweet & Sour Charity
Apr 4, 2000 · 22 min
After winning concert tickets from a radio contest, Grace vows to get more involved and she volunteers herself and Will to help out at the community center. Unfortunately, her charitable work conficts with the concert. Meanwhile, while collecting clothes to give to the mission, Jack donates a pair of Karen's most-prized shoes.
Directing: James Burrows · Writer: Gail Lerner · Cast: Debra Mooney, Shelley Morrison, Daryl Sabara, Mary Pat Gleason
2x19 An Affair to Forget
Apr 18, 2000 · 22 min
When Rob and Ellen ask Will and Grace to be the best man and maid of honor at their wedding, Grace's sexy past with the groom is exposed when Ellen learns at her bachelorette party that Grace once slept with Rob. Meanwhile, Jack is confused by his reaction to the entertainment at Rob's bachelor party.
Directing: James Burrows · Writing: Alex Herschlag, Laura Kightlinger · Starring: Leigh-Allyn Baker, Gretchen German, Tom Gallop, Steve Paymer
2x20 Girls, Interrupted
May 2, 2000 · 22 min
Despite their history, Grace spends a fun evening with Val [ from ep. # 18 Grace, Replaced] only to have Will suspect her of stealing. Meanwhile Jack becomes attracted to the leader of Welcome Home-an organization for gays who have converted to going straight, so he acts straight to woo the man.
Directing: James Burrows · Writing: Jhoni Marchinko, Jon Kinnally, Tracy Poust · Starring: Neil Patrick Harris, Marianne Muellerleile, Molly Shannon, Loren Freeman
2x21 There But for the Grace of Grace
May 9, 2000 · 22 min
It's a scary glimpse into the future for Will and Grace when they visit their curmudgeonly retired college professor only to discover that he is a bitter old man that has a ""Grace"" of his own. Meanwhile, Karen must confront her most mortal enemy, the kitchen, when Stan requests a homecooked meal for his birthday, and she looks to Jack and Ben to come to her rescue.
Directing: James Burrows · Writer: Michelle Bochner Spitz · Starring: Gregory Hines, Piper Laurie, Orson Bean
2x22 My Best Friend's Tush
May 16, 2000 · 22 min
Grace is thrilled when, thanks to Karen's social connections, she gets the chance to land a prestigious client for her interior-decorating firm. The only problem? She must compete with international design goddess Helena Barnes. To help boost Grace's confidence, Karen assumes the alias of ""Anastasia Beaverhausen"" to dig up dirt on the socialite. Meanwhile, Jack tries marketing an odd invention: a tush pad for riding the New York City subway.
Directing: James Burrows · Writing: Rob Lotterstein, Ellen Idelson · Starring: Joan Collins, Doug Ballard, Rod Britt, Martin Morales
2x23 Ben? Her? (1)
May 23, 2000 · 22 min
To help make peace between Grace and Ben, Will has them both over to dinner, only to have their relationship go beyond friendship. But then Will finds out that Ben is dating someone else. Meanwhile Jack catches Rosario in a clinch with a lover and learns that she wants a divorce.
Directing: James Burrows · Writers: Max Mutchnick, David Kohan · Starring: Jo Marie Payton, Corey Parker, Gregory Hines, Shelley Morrison
2x24 Ben? Her? (2) Season Finale
May 23, 2000 · 22 min
Forced by his boss to betray both of his friends, Will quits--only to discover that everything isn't as it seems. Frustrated, he leaves a lost Jack and Grace behind and ends up on a tropical island without a care in the world. Until Ben shows up.
Directing: James Burrows · Writer: Jeff Greenstein · Starring: Jo Marie Payton, Corey Parker, Gregory Hines, Shelley Morrison