Join or Sign In
Sign in to customize your TV listings
By joining TV Guide, you agree to our Terms of Use and acknowledge the data practices in our Privacy Policy.
24 Episodes 1999 - 2000
Series 2 sees a big change in the dynamics as Grace decides to move out - even though it is only across the hallway from Will's flat. Grace then, not liking how WIll runs the tenant's association, decides to run against him in the elections. Later, Will finds himself unemployed, Will and Jack share a kiss on national television and an old friend asks Will for some of his sperm.
Episode 1
Tue, Sep 21, 1999 30 mins
In the Season 2 opener, the platonic pair find life even messier without each other after Grace moves...across the hall. Meanwhile, Karen informs Jack that his marriage-for-show to Rosario must go on in order to keep her maid in America.
Episode 2
Tue, Sep 28, 1999 30 mins
Grace gives Will a run for his money when she enters his unopposed race to be named tenant-board president. Meanwhile, Jack hits the jackpot when Karen tries to buy his forgiveness after she loses his Guapo.
Episode 3
Tue, Nov 2, 1999 30 mins
A flattering newspaper photo gains Grace the attention of an old crush who was never one to keep abreast of her before. Meanwhile, Jack is destroyed to learn that Will had a thing with his former fling.
Episode 4
Tue, Nov 9, 1999 30 mins
Grace hits the roof when her matchmaking mum visits with yet another man in tow. Unfortunately, he's perfect...for Will. Meanwhile, Jack and Rosario meet with an INS agent who's well acquainted with Jack's past.
Episode 5
Tue, Nov 16, 1999 30 mins
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.
Episode 6
Tue, Nov 23, 1999 30 mins
After closing his office, Will takes a job as a waiter for Jack's business. Meanwhile, Grace finds Karen working ...At an adults film.
Episode 7
Thu, Nov 25, 1999 30 mins
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.
Episode 8
Tue, Nov 30, 1999 30 mins
Grace enlists an out-of-practice Will to sue one of her clients (Gregory Hines), a hotshot lawyer who kills her case, but saves Will's career. Meanwhile, Jack and Karen turn a training film set into an adult entertainment experience. Mrs. Freeman: Jo Marie Payton. Marv: Aaron Lustig. Dent: Robert Clendenin. Karen: Megan Mullally.
Episode 9
Tue, Dec 14, 1999 30 mins
Bored with Rob and Ellen's low-rent tastes, Grace and Will dump them for a pair of highbrow downtowners (Tamlyn Tomita, Steve Valentine). Meanwhile, Karen helps Jack face his painful past during a trip to her kid's grade school. Rob: Tom Gallop. Ellen: Leigh-Allyn Baker. John: J.T. Larsen.
Episode 10
Tue, Jan 11, 2000 30 mins
Will kisses up to Karen to appease his new boss (Gregory Hines); Jack and Grace get into hot water over an antique teapot. Porcelain Paul: Harry Van Gorkum. Smitty: David St. James. Mrs. Freeman: Jo Marie Payton.
Episode 11
Tue, Jan 25, 2000 30 mins
When an old school chum (Megyn Price) asks Will to father her child, a jealous Grace tries to thwart her baby-making plans. Nurse: Laura Kightlinger. Jack: Sean Hayes. Karen: Megan Mullally.
Episode 12
Tue, Feb 8, 2000 30 mins
Will's sexy dreams about Grace land him in therapy and send her on a couch trip with his hunky shrink (Markus Flanagan). Meanwhile, Jack and Karen clash over her treatment of Rosario. Jack: Sean Hayes. Karen: Megan Mullally. Rosario: Shelley Morrison.
Episode 13
Tue, Feb 15, 2000 30 mins
Will and Grace are forced to pose as marrieds at his father's awards dinner; Jack's blind date may have a surprising connection to his past. George: Sydney Pollack. John: Perry King. Ted: Mark Ankeny.
Episode 14
Tue, Feb 22, 2000 30 mins
Will and Jack appear on "Today" to protest NBC for yanking a gay kiss from a sitcom episode; Grace seeks Karen's advice on dumping a weirdo beau. Al Roker guest stars as himself.
Episode 15
Tue, Feb 29, 2000 30 mins
Ben sends Will on a blind date; Karen's romantic advice wrecks Grace's relationship with Josh (Corey Parker). Charlie: Michael E. Rodgers. Waiter: Brian Gattas.
Episode 16
Tue, Mar 14, 2000 30 mins
Will has designs on Grace's newest interior-decorating client---his ex-boyfriend (Chris Potter); Karen tries taking her "career" more seriously. Andrew: Christian Zimmerman. Jack: Sean Hayes.
Episode 17
Tue, Mar 28, 2000 30 mins
When Karen's husband, Stan, suffers a heart attack, the gang takes bets on whom the sassy socialite will turn to for emotional support. Karen: Megan Mullally. Will: Eric McCormack.
Episode 18
Tue, Apr 4, 2000 30 mins
As the gang plunges into charity work, Will and Grace direct a kids' play, while Jack infuriates Karen by giving away her favorite pair of pumps. Sister Robert: Debra Mooney. Sally: Mary Pat Gleason.
Episode 19
Tue, Apr 18, 2000 30 mins
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.
Episode 20
Tue, May 2, 2000 30 mins
Grace befriends a sassy kleptomaniac (Molly Shannon); Jack has a crush on the leader of a group of "ex-gays" (Neil Patrick Harris). Kevin: Loren Freeman. Jodie: Marianne Muellerleile.
Episode 21
Tue, May 9, 2000 30 mins
Will and Grace are alarmed when the friendship of two bickering oldsters mirrors their own; Ben (Gregory Hines) impresses Jack and Karen with his hidden talents. Sharon: Piper Laurie. Professor Dudley: Orson Bean. Phil: Gary Beach.
Episode 22
Tue, May 16, 2000 30 mins
A catty socialite (Joan Collins) of Karen's acquaintance vies with Grace for a client; Jack tries marketing an odd invention. Robert: Doug Ballard. Bob: Ken Lerner. Larry: Rod Britt.
Episode 23
Tue, May 23, 2000 30 mins
Part 1 of two. Will is distressed by Grace's affair with his boss, Ben (Gregory Hines). Rosario (Shelley Morrison) wants to divorce Jack, who fears losing Karen's financial support. Josh: Corey Parker.
Episode 24
Tue, May 23, 2000 30 mins
Conclusion. After his legal tussle with Karen, Jack moves in with Will, who is reeling from reversals in his career and love life. Ben: Gregory Hines. Alex: Donald Berman. Houseboy: Michael Edward Thomas.