Seasons & episodes
S1 · E14Big Brother Is Coming (1) 1999-02-16 · 22 min
A "surprise" birthday party for Jack astounds Will when his estranged older brother Sam turns up at the fete at Grace's invitation. Not only do sparks fly between the brothers, but electricity of a different sort crackles between Grace and Sam. Meanwhile, Karen flashes her platinum card for Jack as the pair shop until they drop at a boutique where the snooty salesmen previously had snubbed Jack.
S1 · E15Big Brother Is Coming (2) 1999-02-23 · 22 min
A wary Grace tells Will of her romance with his brother, Sam, and unleashes an avalanche of resentment. While Will wrestles with sibling rivalry, Karen helps Jack come to grips with turning 30 by hiring him as her personal assistant and leads Grace to sort through her true feelings for the Trumans.
S1 · E16Yours, Mine or Ours 1999-03-02 · 22 min
Stunned to find they have a 'date' with the same guy, Will and Grace compete for the affections of a handsome, charming new neighbor at dinner, and even Jack's finely-tuned gaydar can't pick up his preference. Meanwhile, Karen contemplates firing her driver and in a twist of irony asks Grace to role-play firing an incompetent employee.
S1 · E17Secrets and Lays 1999-03-23 · 22 min
The gang retreats to a cabin in Vermont for the weekend, where Grace rekindles romance with an old flame and tries to hide the fling from Will, who's pining on the eve of his would-be anniversary. Meanwhile, Karen's culinary efforts go up in smoke, as does Jack's attempt to cheer Will by dragging him to a gay pub, where the town barber-turned-hair stylist sidles up to him.
S1 · E18Grace, Replaced 1999-04-08 · 22 min
Will finds a "substitute Grace" in Val, a new neighbor who is available for plans with Will while Grace is consumed with work. As Will and Val continue to spend more time together, Grace fears that she has been replaced and fights with Val to regain Will's attention. Meanwhile, Jack seeks support from Karen after the court finds him guilty of slapping a meter maid and sentences him to pick up trash.
S1 · E19Will Works Out 1999-04-22 · 22 min
Will invites Jack to his gym on a "buddy pass," but when he expresses his embarrassment to Grace over his buddy's gay behavior, Jack overhears the comments and looks to set him straight about prejudice. Meanwhile, Grace continues to lend her ear when Karen's marriage hits rocky ground and she and Karen share an evening of girl talk.
S1 · E20Saving Grace 1999-04-29 · 22 min
A successful and arrogant New York publicist hires Grace to decorate his house with the condition that she fixes him up with Will. But there's a problem: Will can't stand the guy. Meanwhile, Jack uses Karen to teach Will how to kiss someone he finds unattractive.
S1 · E21Alley Cats 1999-05-06 · 22 min
When Rob and Ellen admit that they don't have fun playing games with Will and Grace because of Grace's competitive nature, Grace works to change her image. However, as Grace loses her competitive edge, Will's emerges and he convinces his partner to care only about winning. Meanwhile, after learning how to administer CPR from Jack, Karen saves a workman's life.
S1 · E22Object of My Rejection 1999-05-13 · 22 min
Will is stunned to discover that Grace is dating her ex-fiance Danny once again, but he chooses not to interfere after he's accused of being meddlesome. Meanwhile, Jack agrees to take a walk down the aisle with Karen's combative maid, Rosario, who needs a groom to help her smooth out some immigration problems.
S2 · E1Guess Who's Not Coming to Dinner 1999-09-21 · 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.
S2 · E2Election 1999-09-28 · 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.
S2 · E3Das Boob 1999-11-02 · 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.
S2 · E4Whose Mom Is It Anyway? 1999-11-09 · 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.
S2 · E5Polk Defeats Truman 1999-11-16 · 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.
S2 · E6To Serve and Disinfect 1999-11-23 · 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.
S2 · E7Homo for the Holidays 1999-11-25 · 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.
S2 · E8Terms of Employment 1999-11-30 · 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.
S2 · E9I Never Promised You an Olive Garden 1999-12-14 · 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.
S2 · E10Tea and a Total Lack of Sympathy 2000-01-11 · 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.
S2 · E11Seeds of Discontent 2000-01-25 · 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.""
S2 · E12He's Come Undone 2000-02-08 · 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.
S2 · E13Oh Dad, Poor Dad, He's Kept Me in the Closet and I'm So Sad 2000-02-15 · 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.
S2 · E14Acting Out 2000-02-22 · 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.
S2 · E15Advise and Resent 2000-02-29 · 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.