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The Best Episodes of Will & Grace Season 2

Every episode of Will & Grace Season 2 ranked from best to worst. Discover the Best Episodes of Will & Grace Season 2!

Binge this in 8h 48m•Peaking at 8.6/10

Will Truman and Grace Adler are best friends living in New York, and when Grace's engagement falls apart, she moves in with Will. Together, along with their friends, they go through the trials of dating,

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Episode Rankings

  1. #1 Fan Favorite
    Will & Grace Season 2 Episode 7 - Homo for the Holidays
    8.6/10(535 votes)

    S2:E7

    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.

    Director:James Burrows
    Writer:Alex Herschlag

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  2. Will & Grace Season 2 Episode 3 - Das Boob
    8.4/10(520 votes)

    S2:E3

    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.

    Director:James Burrows
    Writer:Jhoni Marchinko

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  3. Will & Grace Season 2 Episode 17 - The Hospital Show
    8.4/10(456 votes)

    S2:E17

    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?

    Director:James Burrows
    Writer:Adam Barr

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  4. Will & Grace Season 2 Episode 6 - To Serve and Disinfect
    8.3/10(463 votes)

    S2:E6

    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.

    Director:James Burrows
    Writer:Katie Palmer

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  5. Will & Grace Season 2 Episode 20 - Girls, Interrupted
    8.1/10(425 votes)

    S2:E20

    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.

    Director:James Burrows
    Writers:Jhoni Marchinko, Jon Kinnally, Tracy Poust

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  6. Will & Grace Season 2 Episode 4 - Whose Mom Is It Anyway?
    8.0/10(450 votes)

    S2:E4

    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.

    Director:James Burrows
    Writer:Alex Herschlag

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  7. Will & Grace Season 2 Episode 10 - Tea and a Total Lack of Sympathy
    7.9/10(417 votes)

    S2:E10

    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.

    Director:James Burrows
    Writers:Jon Kinnally, Tracy Poust

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  8. Will & Grace Season 2 Episode 14 - Acting Out
    7.9/10(441 votes)

    S2:E14

    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.

    Director:James Burrows
    Writers:David Kohan, Max Mutchnick

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  9. Will & Grace Season 2 Episode 19 - An Affair to Forget
    7.9/10(403 votes)

    S2:E19

    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.

    Director:James Burrows
    Writers:Alex Herschlag, Laura Kightlinger

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  10. Will & Grace Season 2 Episode 21 - There But for the Grace of Grace
    7.9/10(411 votes)

    S2:E21

    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.

    Director:James Burrows
    Writer:Michelle Bochner Spitz

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  11. Will & Grace Season 2 Episode 1 - Guess Who's Not Coming to Dinner
    7.8/10(467 votes)

    S2:E1

    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.

    Director:James Burrows
    Writers:Max Mutchnick, David Kohan

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  12. Will & Grace Season 2 Episode 8 - Terms of Employment
    7.8/10(423 votes)

    S2:E8

    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.

    Director:James Burrows
    Writers:David Kohan, Max Mutchnick

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  13. Will & Grace Season 2 Episode 5 - Polk Defeats Truman
    7.7/10(415 votes)

    S2:E5

    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.

    Director:James Burrows
    Writer:Jeff Greenstein

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  14. Will & Grace Season 2 Episode 12 - He's Come Undone
    7.7/10(401 votes)

    S2:E12

    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.

    Director:James Burrows
    Writer:Adam Barr

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  15. Will & Grace Season 2 Episode 23 - Ben? Her? (1)
    7.7/10(381 votes)

    S2:E23

    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.

    Director:James Burrows
    Writers:Max Mutchnick, David Kohan

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  16. Will & Grace Season 2 Episode 24 - Ben? Her? (2)
    7.7/10(312 votes)

    S2:E24

    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.

    Director:James Burrows
    Writer:Jeff Greenstein

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  17. Will & Grace Season 2 Episode 9 - I Never Promised You an Olive Garden
    7.6/10(454 votes)

    S2:E9

    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.

    Director:James Burrows
    Writers:Jon Kinnally, Tracy Poust

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  18. Will & Grace Season 2 Episode 13 - Oh Dad, Poor Dad, He's Kept Me in the Closet and I'm So Sad
    7.6/10(403 votes)

    S2:E13

    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.

    Director:James Burrows
    Writer:Katie Palmer

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  19. Will & Grace Season 2 Episode 22 - My Best Friend's Tush
    7.6/10(388 votes)

    S2:E22

    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.

    Director:James Burrows
    Writers:Rob Lotterstein, Ellen Idelson

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  20. Will & Grace Season 2 Episode 2 - Election
    7.5/10(435 votes)

    S2:E2

    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.

    Director:James Burrows
    Writer:Adam Barr

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  21. Will & Grace Season 2 Episode 15 - Advise and Resent
    7.5/10(401 votes)

    S2:E15

    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.

    Director:James Burrows
    Writers:Jon Kinnally, Tracy Poust

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  22. Will & Grace Season 2 Episode 16 - Hey La, Hey La, My Ex-Boyfriend's Back
    7.5/10(405 votes)

    S2:E16

    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.

    Director:James Burrows
    Writer:Jeff Greenstein

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  23. Will & Grace Season 2 Episode 11 - Seeds of Discontent
    7.4/10(411 votes)

    S2:E11

    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.""

    Director:James Burrows
    Writer:Jhoni Marchinko

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  24. Will & Grace Season 2 Episode 18 - Sweet & Sour Charity
    7.2/10(397 votes)

    S2:E18

    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.

    Director:James Burrows
    Writer:Gail Lerner

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Season 2 Ratings Summary

"Homo for the Holidays" is the best rated episode of "Will & Grace" season 2. It scored 8.6/10 based on 535 votes. Directed by James Burrows and written by Alex Herschlag, it aired on 11/25/1999. This episode is rated 0.2 points higher than the second-best, "Das Boob".