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Will & Grace Season 2 Episodes

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

Guess Who's Not Coming to Dinner

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.

Where to Watch
Will & Grace, Season 2 Episode 1 image

Episode 2

Election

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.

Where to Watch

Episode 3

Das Boob

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.

Where to Watch
Will & Grace, Season 2 Episode 3 image

Episode 4

Whose Mom Is It, Anyway?

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.

Where to Watch
Will & Grace, Season 2 Episode 4 image

Episode 5

Polk Defeats Truman

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.

Where to Watch

Episode 6

To Serve and Disinfect

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.

Where to Watch

Episode 7

Homo for the Holidays

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.

Where to Watch

Episode 8

Terms of Employment

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.

Where to Watch

Episode 9

I Never Promised You an Olive Garden

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.

Where to Watch
Will & Grace, Season 2 Episode 9 image

Episode 10

Tea and a Total Lack of Sympathy

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.

Where to Watch

Episode 11

Seeds of Discontent

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.

Where to Watch

Episode 12

He's Come Undone

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.

Where to Watch

Episode 13

Oh Dad, Poor Dad, He's Kept Me in the Closet and I'm Feeling So Sad

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.

Where to Watch
Will & Grace, Season 2 Episode 13 image

Episode 14

Acting Out

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.

Where to Watch

Episode 15

Advise and Resent

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.

Where to Watch

Episode 16

Hey La, Hey La, My Ex-Boyfriend's Back

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.

Where to Watch

Episode 17

The Hospital Show

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.

Where to Watch
Will & Grace, Season 2 Episode 17 image

Episode 18

Sweet (and Sour) Charity

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.

Where to Watch

Episode 19

An Affair to Forget

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.

Where to Watch

Episode 20

Girls, Interrupted

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.

Where to Watch

Episode 21

There but for the Grace of Grace

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.

Where to Watch

Episode 22

Best Friend's Tush

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.

Where to Watch
Will & Grace, Season 2 Episode 22 image

Episode 23

Ben? Her? Part 1

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.

Where to Watch

Episode 24

Ben? Her? Part 2

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.

Where to Watch
Will & Grace, Season 2 Episode 24 image