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Karen's search for a roommate leads to a high-maintenance individual, who shares many of her eccentricities; Grace and Jack intervene when Will uses painkillers as a crutch.

Karen hires a somewhat immature divorce attorney (guest star Macaulay Culkin) to oppose Will in court.

When Karen's ex-husband dies, she and her British rival (Minnie Driver) have a contest of wills; Leo (Harry Connick Jr.) is needed in Guatemala.

Karen confronts her ex-husband's mistress before inviting everybody for a ceremony on her yacht; Grace suffers from jealousy after meeting her husband's sexy co-worker.

Will and Jack awake in a precarious position while at sea; Grace discovers love letters in Leo's bag from a female colleague.

Grace is vexed when she learns that Leo's ex-girlfriend (Mira Sorvino) is intimately acquainted with Will.

Karen invites Grace and Leo to play tennis at her exclusive club, but her fierce playing style drives Grace away.

Jack lands a speaking role opposite James Earl Jones in an off-Broadway play and gives the veteran actor some pointers.

Will takes Leo on shopping sprees and for high tea to help him rekindle his love of the city; Karen coaches Jack for the annual gay spelling bee.

Will takes his mother for an afternoon stroll and bumps into an attractive bachelor (Dylan McDermott); Karen continues her lifelong quest to hunt down hubby-stealing Lorraine.

An unorthodox doctor (Jack Black) gives Karen her annual physical; Jack begs Will to support his decision to become a student nurse.

Will urges Grace to stay in New York so they can spend some time together; Karen strong-arms Jack's nursing teacher into letting him skip class but still make the grade.

Will catches the eye of a female diner after being stood up; Grace bumps into a man (Tom Everett Scott) with whom she once shared a forgettable encounter; Karen runs into her nemesis, Candice Bergen.

A weak bladder forces Will to entrust Grace with his place in line for Barry Manilow tickets; Grace's mother (Debbie Reynolds) cancels their annual mother-daughter shopping trip to have dinner with Jack.

Grace's freeloading sister (Geena Davis) comes to town to launch her latest business enterprise; Karen spurns Lyle (John Cleese), then changes her mind after Lorraine (Minnie Driver) expresses her disapproval.

A rich plastic surgeon (guest star Hal Linden) tries to buy Will's affection; Grace boycotts a new restaurant.

Will's new client (Dave Foley) falls for Jack; Grace and Karen discover hidden money while trying to fix the plumbing in Leo's cabin.

Will is the only single man in a cooking class full of couples, including Jack and his new boyfriend (Dave Foley); Karen's mother (Suzanne Pleshette) asks Grace to decorate her apartment.

Will and Grace begin a business venture selling apartments; Jack runs into his former acting mentor, Zandra; Karen and Lyle (John Cleese) try to renew romance.

Will and Grace try to break up Jack and Stuart (Dave Foley) so they can sell the apartment for a higher price; Karen demands that Lyle (John Cleese) discipline his daughter (Minnie Driver).

Real estate entrepreneurs Will and Grace face formidable competition on the East Side from a lesbian couple (Edie Falco, Chloë Sevigny); John Edward gives Karen some psychic guidance.

Jack and Grace stumble upon Stuart (Dave Foley) watching a movie matinée in the company of another man; Will tries to teach Karen how to drive.

Grace advises Will to play hard to get with his new boyfriend (Bobby Cannavale); Jack and Karen despair after learning their favorite TV series will be going off the air.

Will introduces his new boyfriend (Bobby Cannavale) to overly critical Grace; Karen tells Jack that their friendship will change after her wedding.

At Tina's (Lesley Ann Warren) urging, Will tries to find out if there is a new woman in his father's life; Jack's son decides to try out for the high-school cheerleading squad.

On the eve of his graduation from nursing school, Jack turns to Will for help writing his commencement address.

Karen moves her wedding to Las Vegas, where Jennifer Lopez agrees to sing at the ceremony.

Karen moves her wedding to Las Vegas, where Jennifer Lopez agrees to sing at the ceremony.

Karen recruits Jack to help her get Jennifer Lopez to listen to Karen's new song; Grace takes out her frustration over her cheating husband on Will.

Jack wangles his way into Janet Jackson's (guest starring as herself) performance tour as a backup dancer.

As she attempts to steal doughnuts at an AA meeting, Grace has a surprise reunion with Val (Molly Shannon); Will and Jack attend a gay television focus group meeting.

Grace accuses Will of being too nice to strangers; Jack has trouble at his new company when his co-workers mock him about his Cher doll.

Despite the fact that Will has never had a happy birthday, his new relationship with Vince (Bobby Cannavale) gives him hope that this one will be.

Will convinces Jack to aid a local gay-bookstore owner to save his store from closing.

Will and Grace decide to invite Vince and Nadine (Kristin Davis) over, but they quickly learn that, despite similarities in friendship, they are polar opposites.

After a great date with someone else, Grace comes home to a garbled message from Leo; Karen and Jack try to set each other up, but things go awry.

Will, Grace, Jack and Karen go on a road trip for Grace's getaway weekend, but Jack and Karen hate the car ride and bail on the plan.

Vince's mother cannot make her traditional holiday feast, so Will volunteers to make a special meal, but Vince's mother refuses to give him any credit; Jack gives Vince's sister (Jamie-Lynn DiScala) pointers on keeping secrets.

Vince's mother is unable to make her traditional holiday feast, so Will volunteers to make a special meal, but Vince's mother refuses to give Will any of the credit; Jack gives Vince's sister (Jamie-Lynn DiScala) pointers on keeping secrets.

Grace accidentally breaks a treasured figurine at Will's mother's (Blythe Danner) holiday party and blames it on another guest.

An old classmate (Jeff Goldblum) tries to get revenge on Karen by becoming the president of Walker Inc.; Will and Grace run into Vince and a co-worker while playing hooky from work.

Will is reluctant to bring Vince to a dinner party at his boss's (Lily Tomlin) home, fearing it will scratch his chances of making partner at the firm.

When Scott Woolley (Jeff Goldblum) tries to get Grace to fire Karen by impersonating a restaurant owner, the women plan a trap for him.

Although Grace tries to ignore St. Valentine's Day, she winds up with a hunky greeting-card writer (Ed Burns); Karen's former nemesis (Jeff Goldblum) tries to win her heart by showering her with gifts.

Grace drags Will along on her first date with Nick (Edward Burns); Karen tries to set Jack up on a date with the neighborhood bird enthusiast (Luke Perry), but things don't quite go as she has planned.