Supporting characters on Will & Grace

This is a list of the supporting or recurring characters and guest stars on the NBC situation comedy "Will & Grace", with information on each of them.

upporting characters

Family members

Grace's family

*Bobbi Adler, Grace's mother, played by Debbie Reynolds. Bobbi is an actress and singer, although her performances are generally with the Schenectady Players, changing gender roles, in plays such as "Death of a Salesperson", "The Music Person" and "Queen Lear". She has a constant desire to meddle in the lovelives of her daughters, is the creator of the Adler family "Told you so" dance, and can always be relied upon to have a song for every occasion. She has, in the past, shown perfect willingness for Will and Grace to get married, despite their sexuality differences.

*Martin Adler, Grace's father, played by Alan Arkin. Portrayed by his family as the stereotypical Jewish patriarch, Martin shows genuine affection for Grace, although remarks he has made suggest Joyce is his favorite. Has been known to pinpoint Grace's flaws without looking up from his "Kojak" and "Baretta" reruns.

*Janet Adler, Grace's older sister, played by Geena Davis. Janet lives in a van and designs jewellery. Her nickname for Grace is "Smudge." It is once implied that she has difficulties with her mother. In the episode "Lows in the Mid-Eighties," Will asks if Grace has another sister named Janet and Bobbi quickly answers "No!"

*Joyce Adler, Grace's younger sister, played by Sara Rue. It is suggested that Grace and Joyce had a not too friendly relationship growing up and that Joyce was formerly a binge eater. She is often hostile to Grace, but one word from Will and she tends to giggle and act girlish; it appears that she, like Grace before her, harbors a crush upon Will.

*Lila Marcus, Grace and Leo's daughter, played by Maria Thayer. Lila was conceived by Leo and Grace on an airplane, during a period where her parents had temporarily divorced. Initially she was going to be raised by Will and Grace, but instead her parents remarried shortly before her birth. She appeared on screen only during the series finale, where upon going to college, she met and would later marry Will's son, Ben

Will's family

*Marilyn Truman, Will's mother, played by Blythe Danner. A typical WASP, Marilyn regularly drinks, collects Lladró statues and treats them as if they were her children, and put up with her husband's regular affairs until their ultimate separation. She is not a fan of musical theater - once claiming that "Les Misérables" was unrealistic because "poor people don't sing that much" - but was impressed with "Mamma Mia!". She does not like the jokes Grace and Karen make about Will's sexuality saying, "Is that a gay joke? I don't like that."

*George Truman, Will's father, played by Sydney Pollack. He had trouble dealing with telling others of his son's sexuality, initially telling his friends Will was married to Grace. He died in season 8, only days after having a fight with Will in which he admitted he would rather Will weren't gay.

*Sam Truman, Will's brother, played by John Slattery in season one and Steven Weber in season 8. He had a falling-out with Will over comments Will made about his wife, but reconciled after he had a one-night stand with Grace. He eventually divorced his wife and gained full custody of their two children.

*Paul Truman, Will's brother, played by Jon Tenney. Paul has never really come to terms with his brother's sexuality and often behaved like a childish bully, belittling and insulting Will.

*Peggy Truman, Paul's wife and Will's sister-in-law, played by Helen Slater. She was only shown in one episode and came off as Waspish and suspicious of Grace's friendly behavior towards her husband.

*Tina, played by Lesley Ann Warren, is George's mistress. She began a relationship with George while he was still married to Marilyn, but was dismayed to learn that George was then seeing his ex-wife behind her back. Ultimately she and Marilyn come to an understanding that they will share George between them without him knowing what is going on. This arrangement apparently ended not long before George's death.

*Jordan Truman, Sam's son and Will's nephew, played by Reed Alexander. Flamboyant Jordan incenses Will since Marilyn is incredibly accepting of him even though she was not at first accepting of Will. His nickname is Jordy.

*Casey Truman, Sam's daughter and Will's niece, played by Kyla Dang. Casey was adopted by Sam and his ex-wife.

*Ben Truman, Will and Vince's son, played by Ben Newmark. Appearing only during the series Finale, Ben was apparently born from a surrogate mother and the sperm of Will and/or Vince. Upon going to college, he met and would later marry Grace's daughter, Lila. He was apparently named after Will's former boss, Ben Doucette.

Karen's family

*Stan Walker, Karen's third husband (little is known about her first two), an unseen character. An obese man, Stan has worn a toupee since his teens. Stan has two children from a previous marriage to a woman named Kathy. Karen fell in love with him in the 1980s but they didn't marry until 1995. Jailed for tax evasion in season four, Stan began an affair with a cafeteria worker named Lorraine (played by Minnie Driver) and - after his release in season five - continued the affair, ultimately separating from Karen because of it. He died at the end of season five, but at the end of season seven he revealed himself to Will. He had faked his death and was hiding out with the aid of the government. He and Karen reconciled in season 8 but subsequently faced maritial difficulties and divorced. Stan's popularity with fast food establishments led to Pizza Hut taking out a full-page ad in the "New York Times" to congratulate him on his release from prison; Taco Bell also did a flyover at his funeral.

*Mason Walker, Stan's son, another unseen character. He is known to Karen as "the fat one".

*Olivia Walker, Stan's daughter, played by Hallee Hirsh. Although she has had fun times with Karen, such as sticking food to the floor to see how long Mason will spend trying to eat it, she also has problems with her stepmother.

*Lois Whitley, Karen's mother, played by Suzanne Pleshette. A con artist who used Karen in her early schemes. She and Karen reconcile in season 4, with the help of Jack.

*Virginia "Ginny" Delaney, Karen's sister, played by Bernadette Peters. In 1963, as a child, she was injured in a brutal game of Twister with Karen.

*Barry, Karen's cousin, played by Dan Futterman. Originally a gay bookish homebody, Karen had Will and Jack bring him out of his shell to become an attractive person who both Will and Jack fall for.

*Sylvia Walker, Karen's mother-in-law is a woman that 'strikes fear in her heart-facsimile'. A kind, but homophobic old woman, Sylvia appeared in one episode to accompany Will and Jack to a club.

Jack's family

*Judith McFarland, Jack's mother, played by Veronica Cartwright. Despite the obvious clues, Judith did not learn about Jack's sexuality until he was 30. She was impregnated with Jack while at a swinger's costume/pool party.

*Daniel McFarland, Jack's stepfather, played by Beau Bridges. Daniel always had trouble relating to Jack, due to his athleticism and Jack's lack thereof. Despite Jack's statements otherwise, Daniel is shown to be a caring man who is at least recently trying to reconnect with Jack.

*Joe Black, Jack's biological father. Never portrayed on screen, Joe was revealed to have attended a swingers costumed/pool party during the 60's, where he was dressed as Richard Nixon. During the party he impregnated Judith, who was dressed as the rear end of a horse. He died several years before Jack discovered that Daniel McFarland was not his real father.

*Elliott, Jack's son, played by Michael Angarano. Shortly after learning of his biological father's death, Jack met Elliott - his biological son created from sperm Jack donated at age 17. He is described by Will as "Polite, Sweet, and Kind" which he says is the reason Karen initially dislikes him. His relationship with Jack is shown to be very close, although they have a brief rift when Elliott prepares to leave for college during the last season.

*Bonnie, Elliott's mother, played by Rosie O'Donnell. Initially, Bonnie did not want Jack to be included in Elliott's life. Bonnie was a lesbian, but was not open about her sexuality to Elliott. She felt jealous that Jack found it easy to be open with Elliott about his sexuality when she did not feel she could be.

Friends

*Rob & Ellen, Will & Grace's close friends, played by Tom Gallop and Leigh-Allyn Baker. Ellen and Grace were best friends since college, as were Rob and Will, and the two couples have regularly played charades and other games during dinner parties. Grace, however, also slept with Rob sometime in Season One when they were both going through break-ups and felt emotionally vulnerable, a fact that didn't come up until Rob & Ellen's wedding. The couple, however, did get married and have since had three children, the youngest named Roman (which is the name of Debra Messing's real-life son, born in 2004). They announced their separation at a dinner date with Will & Grace. Rob and Ellen only wanted to separate so that they could try dating again. They got back together after Grace went on a tirade, saying that they were "too old" to date, and they should stay together for the sole reason that "no one else would take them."

*Joe & Larry, Will & Grace's close friends, played by Jerry Levine and Tim Bagley. A gay couple, once party animals, Joe and Larry adopted a baby girl Hannah in season three. Karen occasionally refers to them as "Mo and Mary," with "Mo" being a play on the word "Homo."

*Val Bassett, a neighbor of Will & Grace, played by Molly Shannon. Slightly crazy and definitely alcoholic, Val originally befriended only Will, until Grace eventually discovered common interests with her. Both of them still consider her crazy, however, as does Jack, who found her as an uninvited guest in his bedroom.

*Beverley Leslie, played by Leslie Jordan, is the very short and effeminate rival of Karen. He belongs to the same social society as Karen, and they often go from friends to enemies. He has a wife named Crystal, who is considerably older than he is, but he is more interested in his "business associate" Benji, who he is almost always seen out with. The characters see him as a closeted gay man, and that his wife is a ruse to hide his sexuality. Whenever he appears, he often catches the characters by surprise, especially Karen. Sometimes his appearance comes after a character saying something that could be comically associated with him. For instance, while discussing dessert, Jack said, "I want something small and fruity, with ladyfingers," and immediately following that line, Beverley Leslie entered. He often tries to take Karen down a peg and embarrass her, especially when she is alone during the "traditional spotlight dance". However, Karen also enjoys ridiculing him for his height, and usually gets the last laugh in their battles. He was dating a reluctant Jack (who was persuaded by Karen to date Leslie in order to support her excessive spending habits and addictions to drugs and alcohol) during the season finale when he was swept off the balcony by a strong gust of wind and died. He left Jack his estate in his will.

*Rory, Toby, and Josh. Friends of Jack who are never seen but mentioned in various episodes. Early in Season 3, Rory is mentioned as being into Asian men. In Season 4, Josh, Toby and Jack watch a video of Will freezing up on camera talking about Stanley Walker, but Josh and Toby leave before Will gets home.

Love interests

Grace

*Dr. Marvin "Leo" Markus, played by Harry Connick, Jr.. A Southern-born Jewish doctor who met Grace when she ran into a lamppost, Leo soon charmed even Will, and ended up proposing to — and marrying — Grace. A supporter of Doctors Without Borders, Leo was rarely in the country and had a one-night stand in Cambodia that led to the demise of their marriage. They reunited for one brief fling on a plane to London in season 8, which resulted in Grace becoming pregnant. In the series finale, Grace and Leo raised their daughter Lila, who ultimately married Will's son Ben.

*Nathan, played by Woody Harrelson. Grace's neighbor in season 3 who became her boyfriend. They appeared to be a good match, but early in Season 4 he abruptly proposed to her during sex and she became distraught at the unromantic nature of his proposal, and forced him to take it back and ask again in a more romantic way. For several days they were awkward around each other, and fearing that their relationship was over, Grace proposed to Nathan, who reluctantly refused, and broke up with her.

*Ben Doucette, played by Gregory Hines. Introduced in mid-season 2, Grace sued him after he violated her contract of employment and fired her without reimbursment for expenses she incurred while decorating his house. Although at first he played Grace and Will, who was representing her, he eventually gave her the money voluntarily and hired Will at his renowned law firm. Grace and he disliked each other for the rest of the season, until the season finale when Ben showed her his more humane face when Will invited him to dine with them. They then started a happy semi-monogomous relationship that lasted for roughly six months, until they broke up early in Season 3 when they realized that they were not in love.

*Josh, played by Corey Parker. A sweet, romantic New Age-y man whom Grace dates in season 2. Grace often has issues with him being way too affectionate and nice, to the point of being obnoxious. The two broke up, because Jack confessed that he had slept with him.

*Nick, played by Edward Burns. A greeting-card writer who falls for Grace when he meets her one Valentine's Day in season 7, after her divorce from Leo. Nick is the first guy Grace starts dating right after her divorce with Leo. They decide to break up when he has to go out of the country to work on a screenplay he wrote.

*Tom Cassidy, played by Eric Stoltz. An old friend of Grace's, now married, with whom she reunited briefly at the end of season 7. He asks her to help design his and his wife's home, yet she still feels chemistry with him and kisses him. She nearly takes it further, but feels guilty and breaks it off with him at the beginning of season 8.

*Danny, played by Tom Verica, Grace's long-term boyfriend from roughly 1995–1998, whom she nearly married in the Pilot. She realized after Will advised her against the marriage, that Danny was too immature for her, and practically left him at the altar. They reunited at the end of season 1, much to Will's dismay. Yet again Grace decided that she did not love him, and after roughly a week (one episode) Grace broke up with him offscreen.

* Mark, placed by Ken Marino is another of Grace's partners in Season 3, Three's a Crowd, Six is a Freakshow. She dumped him because he has 6 toes, although the actual 6th toe was not seen in the episode

Will

*Vince D'Angelo, played by Bobby Cannavale. An Italian-American police officer, but not a very good one, Vince met Will when the two went up against each other in traffic court over a ticket given to Karen. Vince was friends with Joe & Larry, and was Will's first long-term relationship in the series' run. They ultimately broke up after Vince lost several jobs in a row and needed some time alone. In season 8, he ran into Will again, and - when they both attended Will's father's funeral - they began to realize they still had feelings for each other, eventually rekindling their romance. In the show's finale, Will and Vince eventually raised a son - Ben - together - who ultimately married Grace's daughter Lila.

*Barry, played by Dan Futterman. Karen set up her hopeless cousin Barry with Will shortly after he came out. Will and Jack soon undertook a Pygmalion-esque attempt at turning Barry into a more confident gay man, ending when Will fell for Barry but Barry wanted to play around before settling down.

*James Hanson, played by Taye Diggs. Will's boyfriend in season 8. He is Canadian and married Grace to get a green card. When Will discovered more about James's dislikable personality, they broke up and Grace got the marriage annulled.

*Matthew, played by Patrick Dempsey was a sports reporter Will met at the Banana Republic while trying to help Jack woo him. Jack and Matt had little in common and Will instead found himself in a relationship with him. They dated for a while but Matt's refusal to come out led to their break-up.

*Diane, played by Mira Sorvino. The third of the three women Will has ever dated, the only one he ever slept with (although he left before she woke up the next morning). She is also one of Leo's exes. Both of these facts made Grace very jealous. Diane stated that Will was much better in bed than Leo. Diane was shown briefly (though she had no lines) in the season-3 episode titled "Lows In the Mid-Eighties" but was played by a writer's assistant, Lisa Borgnes, and had red hair.

*Claire, played by Megyn Price. Will's high school friend/girlfriend, the first of the three women Will has ever dated, the second being Grace. She lives in Paris and asked Will to donate sperm so that she could have a baby, but Will realized that if he was going to donate sperm, he wanted to donate it to Grace.

*Michael, played by Chris Potter mostly unseen character, Will's lover of seven years, did make an appearance in the "Hey La, Hey La, My Ex-Boyfriend's Back" episode, which was aired on March 14, 2000. They broke up before the series began. He is mentioned sometimes by Will and also by Grace. Will admits that it has been hard letting him go.

Karen

*Lyle Finster, played by John Cleese. The father of Stan's mistress, Lorraine, oddly became Karen's fourth husband for about 20 minutes until the couple realized how little they had in common outside of the bedroom.

*Scott Woolley, played by Jeff Goldblum. The man who lost to Karen for School Body President, and has spent his life hatching schemes to ruin her. Sadly, his schemes are often poorly thought out and eventually Grace realises that he doesn't hate Karen, he loves her. However his attempts to woo her are as misguided as his previous ones. Woolley also has a dreadful sense of word-play (i.e. "The Scotty Mammoth", "Beam me up, Woolley"). He also changes his first name when using an alias, whereas most people change their last names.

*Lionel Banks, played by Rip Torn. A bachelor who falls for Karen, under her alias Anastasia Beaverhausen, while Stan is in jail, and tempts her into having an affair.

*Malcolm Widmark, played by Alec Baldwin. A government agent who helped Stan fake his death, he had a brief relationship with Karen before she reconciled with Stan, and Malcolm went on a government mission to Sri Lanka.

Jack

*Stuart Lamarack, played by Dave Foley. A client of Will's who becomes Jack's longest relationship, until Jack cheats on him.
*Jack has countless short-term lovers over the course of the series (and presumably long before and after), although most are never mentioned by name (or mentioned at all, it is constantly assumed, and not always stated, that he has mulitple boyfriends in every episode). Due to Jack's hilarious promiscuity and his habit of forgetting his boyfriends' names it would be literally impossible to list all of his love interests over the course of the show. Will once joked that if he was to avoid every man that Jack had ever slept with, "That would leave me with...women!" Jack also commented that he goes on thousands of dates a year.

Other supporting characters

*Harlin Polk, played by Gary Grubbs. A major client of Will's in season one, who ultimately fires him.

*Mrs. Freeman, played by Jo Marie Payton. An executive assistant at Doucette & Stein, her most commonly uttered phrase is "Mm-hmm" which is often said with sass.

*Zandra Zoggin, played by Eileen Brennan. Jack's crusty acting coach, a former Hollywood star. After Jack takes over her class, Zandra loses her interest in life and ends up in an actor's retirement village.

*Dr. Jay Markus, played by Tom Skerritt. Leo's father, and Grace's eventual father-in-law, whom she meets during brunch, thinking he is one of Leo's "old friends."

*Eleanor Markus, played by Judith Ivey. Leo's mother and a noted author of three books on theatre, she meets Grace during brunch alongside her husband. She also is the first to tell her new daughter-in-law her son's actual name, Marvin.

*Mr. Stein, played by Gene Wilder. The senior partner at Will's firm, an eccentric man who takes a liking to Will. He refers to Will as "Gay Will," but without at first realising that Will is actually gay. He and Karen fancied each other, but nothing came of it. He was away from the office for some time prior to season 5 due to a mental breakdown.

*Margot, played by Lily Tomlin. A senior partner at Will's firm who apparently takes over after Mr. Stein. She is also quite eccentric and sarcastic. She promotes Will to partner.

*Dorleen, played by Parker Posey. Jack's bitchy, chain-smoking boss during his brief tenure at Barneys New York.

*Lorraine Finster, played by Minnie Driver. Stan's mistress, a slutty prison cafeteria worker (and, it is implied, prostitute) who instantly forms a hatred of Karen. Was Karen's stepdaughter very briefly (for about 20 minutes) when her father, Lyle, married Karen, although Lorraine was unable to attend the wedding due to an aggressive strain of herpes that kept her from flying. According to the episode "The Accidental Tsuris," she was raised as a girl despite being genetically male or perhaps hermaphroditic.

*Mr. Zamir, played by Marshall Manesh. An obnoxious tenant in Will and Grace's building with a tendency to take off his shirt and to steal Will and Grace's newspapers.
*Benji, played by Brian A. Setzer. Beverley Leslie's "business associate" and boytoy.

*Joanne, played by Emily Rutherfurd. A student of Zandra's acting class, who becomes a devoted follower of Jack and his "McFarland method."

*Russell, played by Jon Fleming. A handsome, muscular student of Zandara's acting class who is often asked by Jack to take his shirt off when Jack is teaching the "McFarland method."

*Julius, played by Neil Vipond. Bobbi Adler's close friend and pianist.

*Gary, played by Jamie Kaler. Will's coworker at Doucette and Stein.

*Nurse Sheila, played by Laura Kightlinger. A rather creepy nurse who works at the sperm bank (where Will visits, intending to donate sperm to his high-school friend Claire), who openly admits she is a whore in season 4 (when Will and Grace are planning to have a baby together), and thereafter seems to appear whenever Will goes into a hospital. She was pregnant in season 8 and attended birth classes alongside Grace. Her brother, a doctor played by guest-star Jack Black (Kightlinger's real-life former boyfriend) claims he would be "tappin' that big time" if they weren't related.

*Dave, played by Matthew Botuchis. The only openly straight worker at OutTV, the gay network where Jack works in the last seasons. Jack, unimpressed with his heterosexuality, refers to Dave as "Elizabeth."

*Jamie, played by John Ducey. The station manager at OutTV.

*Tim, played by Mark Harelik. A member of Senior Management at OutTV.

*Jimmy, played by Sam Pancake. A colleague of Jack's at OutTV.

*Smitty, played by Charles C. Stevenson Jr. A bartender who regularly serves Karen at different establishments. She has been known to call other bartenders "Smitty," even when they tell her it isn't their name. If Karen is depressed, Smitty will tell her a tragic story about his own life, which she will laugh at, thinking it is a joke.

Guest stars playing one-time characters

* Shohreh Aghdashloo, as a Jewish Iranian hired by Grace
* 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, who examines Karen; he 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 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, the lawyer representing Karen in the case of 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
* Ellen DeGeneres, as Sister Louise, a nun to whom Will sells Grace's (now deceased) 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 Garcia, 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 gay 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 former lesbians and gays
* Alex Kapp Horner, as Alice Robinson, one of Grace's former classmates
* Stacy Keach, as Wendell Schacter, a former colleague of Jack's who usurps his acting class
* 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 briefly becomes Will's "sugar daddy"
* 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
* Dylan McDermott, as Tom, a boyfriend of Will's who is very closely attached to his elderly mother
* Julian McMahon, guy in 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 INS 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, playing 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 both Will & Jack
* Brandon Routh, as Sebastian, a stud who replaces Will in his May/December romance with Hal Linden's character
* Chloë Sevigny, as Monet, a wealthy lesbian real-estate agent who falls for Will
* Nicollette Sheridan, as Dr. Danielle Morty, a fellow doctor who wanted Leo sexually
* Jamie-Lynn Sigler, as Rose, Vince's lesbian sister
* Britney Spears, as Amber Louise, a conservative Christian and a "hardcore lesbian" as she describes herself, sidekick to Jack, on his talk show, featured on the fictional "Out TV" network
* Wendie Jo Sperber, as Grace's short-lived housekeeper
* Sharon Stone, as Georgia Keller, Will and Grace's therapist
* Wanda Sykes, as Cricket, a woman Karen offers to pay to carry her child
* Rip Torn, as Lionel Banks, a man with whom Karen almost cheats on Stan 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

Guest stars playing themselves

* Kevin Bacon
* Candice Bergen
* Cher
* Sandra Bernhard
* Katie Couric
* John Edward
* Rudy Galindo
* Hall & Oates
* Deborah Harry
* Janet Jackson
* Elton John
* James Earl Jones
* Matt Lauer
* Jennifer Lopez
* Josh Lucas
* Patti LuPone
* Barry Manilow
* Martina Navratilova
* Bebe Neuwirth
* Al Roker
* George Takei
* Rip Taylor