- Jennifer Lopez, as herself, sings at Karen's wedding to Finster and then hires Jack to dance in her tour.
- Janet Jackson, as herself. Jack tries out to be her dancer.
- Shohreh Aghdashloo, as Pam, an incompetent Iranian hired by Grace who she then fires upon realizing Pam is Jewish and thus she 'doesn't owe (her) anything'.
- Rosanna Arquette, as Julie, a masseuse who lives in the same building as Leo and Grace.
- Jason Biggs, as Baby Glenn, a former local celebrity and a guest at Will's auction.
- Roscoe Lee Browne, as Linus, owner of a landmark gay bookstore about to be turned into a gym.
- Jack Black (uncredited), as Dr. Isaac Hershberg. He examines Karen and is also the brother of the occasionally seen nurse Sheila, played by show writer and Black's girlfriend at the time, Laura Kightlinger.
- Richard Chamberlain, as Clyde, an elderly man who Will brings to game night, much to Grace's chagrin
- Glenn Close, as Fannie Lieber (a play on celebrity photographer Annie Leibovitz), a noted photographer who takes Will and Grace's picture.
- Joan Collins, as Helena Barnes, a designer with whom Grace competes for a job, and a nemesis of Karen's.
- Macaulay Culkin, as Jason Towne, a lawyer representing Karen in her divorce from Stan.
- Tim Curry, as Marion Finster, Lyle Finster's brother.
- Matt Damon, as Owen, Jack's heterosexual rival, pretending to be gay to vie for a spot in the Manhattan Gay Men's Chorus.
- Kristin Davis, as Nadine, Vince's straight female friend – the same as Grace is to Will.
- Ellen DeGeneres, as Sister Louise, a nun to whom Will sells Grace's uncle's old car.
- Michael Douglas, as Gavin Hatch, a somewhat closeted gay police detective who becomes attracted to Will and has issues with seeing food stuck in people's teeth.
- Christine Ebersole, as Candy Pruitt, another of Karen's rivals.
- Edie Falco, as Deirdre, one of a pair of lesbian real-estate "flippers".
- Victor Garber, as Peter Bovington, a former actor now working as a doorman.
- Andy García, as Milo, a restaurateur, and lover of Karen's, who fails to phone Karen after their date and is confronted by Grace.
- Sara Gilbert, as Cheryl who, like Will, is a Barry Manilow fanatic, a.k.a. "fanilow".
- Seth Green, as Randall Finn, a former child star.
- Clark Gregg, as Cameron, Jack's wealthy boyfriend who becomes Grace's client.
- Neil Patrick Harris, as Bill, the leader of a group of so-called "former" lesbians and gays.
- Alex Kapp Horner, as Alice Robinson, one of Grace's former classmates.
- Peter Jacobson, as Paul Budnik, an overbearing guy who Will dates but is more fond of his dog.
- Stacy Keach, as Wendell Schacter, a former colleague of Jack's who usurps his acting class.
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- Michele Lee, as Lucille, one of the lesbians who ended up dancing with both Will & Jack.
- Hal Linden, as Alan Mills, an elderly gay man who befriends Will and bestows expensive gifts upon him.
- Natasha Lyonne, as Gillian, Grace's intern who decides to turn into the spitting image of Karen.
- Madonna, as Liz, Karen's room-mate.
- Lee Majors, as Burt Wolfe, a friend of Grace's father.
- Camryn Manheim, as Psychic Sue.
- Jason Marsden, as Kim, a friend of Leo's.
- Dylan McDermott, as Tom, a boyfriend of Will's who is very closely attached to his elderly mother.
- Julian McMahon, guy in an elevator who Grace flirts with.
- Demi Moore, as Sissy, Jack's former babysitter.
- Sharon Osbourne, as a bartender in No Sex N' in the City.
- Peter Paige, as a gay Immigration and Naturalization Service officer whom Jack tries to convince his marriage with Rosario is real.
- Scott Patterson, as Grace's former high school crush in "Das Boob".
- Sara Paxton, as Melanie, the head cheerleader at Elliot's school.
- Luke Perry, as Aaron, a "hot gay nerd" bird-watcher on whom Jack develops a crush.
- Jeremy Piven, as Nicholas, Grace's ex. who asks Grace if she wants to join him in a threesome with his current lover.
- Chita Rivera, as Lenore, one of the lesbians who ended up dancing with Will & Jack.
- Brandon Routh, as Sebastian, a stud whom Hal Linden's character replaces Will with, after the two have a falling out over Will's misinterpretation of their relationship.
- Chloë Sevigny, as Monet, a wealthy bi-sexual real-estate agent who falls for Will.
- Nicollette Sheridan, as Dr. Danielle Morty, a fellow doctor who wanted Leo sexually.
- Jamie-Lynn Sigler, as Ro, Vince's lesbian sister.
- Britney Spears, as Amber Louise, a conservative Christian and a "hardcore lesbian" as she describes herself, and a co-host to Jack on his talk show.
- Wendie Jo Sperber, as April, Grace's short-lived housekeeper.
- Sharon Stone, as Georgia Keller, Will and Grace's therapist.
- Larry Sullivan, as Robert, Will's ballet dancing boyfriend on the holiday episode "Jingle Balls".
- Wanda Sykes, as Cricket, a woman Karen offers to pay to deliver a child for her.
- Tamlyn Tomita, as Naomi, half of the couple that takes Will and Grace out all night.
- Rip Torn, as Lionel Banks, a man with whom Karen almost cheats on Stan with during his incarceration.
- Stuart Townsend, as Edward, Karen's pansexual pastry chef, who ends up "sexing" Will, Karen, and Rosario.
- Tracey Ullman, as Anne, the instructor of a couples cooking class that Will, Jack, and Jack's boyfriend Stuart attend.
- Steve Valentine, as Kai, half of the couple that takes Will and Grace out all night.
- Steven Webber, as Will's brother
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