Ranking 101 ‘Will & Grace’ Guest Stars: Part 1

In celebration of the return of NBC’s Will & Grace, Joey Moser ranks the 101 famous faces that interacted with one of television’s most beloved casts.  

Will & Grace is one of the most celebrated sitcoms of all time. During its original 8-season run on NBC, the sitcom hosted many guest stars and celebrity cameos. There was even a point where the comedy series was accused of “celebrity baiting” just to earn ratings. In its later seasons, Will & Grace would sometimes have upwards to three appearances in just one 22-minute episode.

So far, we know that former First Lady Michelle Obama, Tony-winner Ben Platt and Emmy-winner Jane Lynch are signed on to stop by in this new ninth season. Will & Grace‘s return airs Thursday night on NBC.

In celebration of its return, we will be taking a look at the 101 best guest appearances from the entire show. This list includes everything from one scene, nameless cameos (Sharon Osbourne as an advice-giving bartender) to recurring romantic interests from all four of the main leads (looking at you, Woody and Bobby!). To get it out of the way now, Shelley Morrison, our beloved Rosario, will not be on this list since she was considered a regular.

101. Charles C. Stevenson as Smitty
Various episodes

We kick off our list with a beloved and undervalued performer. Karen Walker spends a lot of time at hotel bars, and her beloved Smitty is always there to lift her spirits–even if it comes at his own expense. He’s lost a lot in his lifetime, but his misery always delivers huge laughs.

100. Sharon Osbourne as Nonny
Episode – “No Sex ‘n’ the City” – Season 6

Osbourne won her role in this episode at a charity auction for The Trevor Project. Grace advises Will to play aloof with Vince (Bobby Cannavale) in order to not appear needy. When Will’s behavior puts Vince off at a bar, Osbourne steps in to offer some sage advice. We’d much prefer to have this relatable matriarch in a much larger guest role and not just slinging drinks. Imagine how much fun she’d be opposite Karen?

99. Martina Navratilova as Herself
Episode – “Lows in the Mid-Eighties: Part 1” – Season 3

Martina only has a very brief cameo in this flashback, but it’s one of the best episodes of the entire series. As Will and Grace recount how they found out about Will’s sexuality, Karen continually interrupts them by detailing all of the men that were dying to marry her in 1985. Martina is the last suitor who, during their breakup at a disco, exclaims, “But Karen, I was straight before I met you.”

98. Josh Lucas as Himself
Episode – “Whatever Happened to Baby Gin?” – Season 8

Poor Josh Lucas. It’s not really his fault that Hollywood has never found exactly what to do with him, but he’s always been seen as a hybrid between Bradley Cooper and Ryan Gosling. When Jack is devastated by the news that his voice has been dubbed over on his new cop show, Lucas reveals that all leading men are dubbed. His high, squeaky “real” voice isn’t funny as much as it is cringe-worthy. At least he got to be on The Mysteries of Laura with Debra Messing!

97. Stacy Keach as Wendell Schacter
Episode – “From Queer to Eternity” – Season 7

Keach is a very well-respected character actor who is always welcome on screen (remember all that praise for Nebraska?). Wendell took over teaching Jack’s acting class after he abandoned it, and Wendell’s usage of The McFarland Method to seduce women (and not hot, dumb straight guys) sickens Jack enough to try and reclaim his teaching position.

96. Jason Biggs as Baby Glenn
Episode -“The Hole Truth” – Season 8

Biggs has always been game enough, sure, but viewers aren’t always excited about him popping up on screen. Baby Glenn is still riding his 15 minutes of fame of falling into a hole and being trapped there for 3 days. The double entendres just write themselves, don’t they? Jack appears alongside him in a gay celebrity auction, but people aren’t as enthusiastic to bid on our favorite Out TV talk show host. Jason Biggs gets more money than Sean Hayes? Puh-lease!

95. Luke Perry as Aaron
Episode – “The Birds and the Bees” – Season 7

Karen assumes that a pervert is spying on her through her penthouse window, but upon further inspection it’s just “The rarest of all specimens…the Hot Gay Nerd!” who is simply bird watching. Perry gets points for playing against stud muffin type, but I wish he was given an opportunity to bask in his heartthrob glory.

94. Matt Lauer as Himself
Episode – “Bathroom Humor” – Season 8

Lauer gets points for participating in the series’ second live episode, but he’s in and out in minutes.

93. Seth Green as Randall Finn
Episode – “Friends with Benefits” – Season 7

It’s the bitch slap heard round the world! Green’s Randall is set to be the star of Jack’s Out TV talk show, but his diva behavior pushes Jack to the point and smacking him Dynasty-style. Randall quickly exits and Jack becomes the face of the show. For a long stretch of his career, Green has played loud, obnoxious characters, and his Randall is pretty grating. The episode features one of the best quotes about television: “Pitch. That’s industry speak for when people get so excited for an idea, they pitch a tent in their pants!”

92. Peter Paige as Roger
Episode – “Whose Mother Is It, Anyway?” – Season 2

Has this ever happened to you? You’re gay but marrying your bestie’s El Salvadorian maid in order for her to stay in the country? And then the INS agent in charge of your case happens to be someone you kind of slept with? Paige’s straight-laced agent’s delivery of “Uh…you’re gay!” is one of the best in episode. Paige also played openly gay Emmett Honeycutt in Showtime’s Queer as Folk.

91. Lainie Kazan as Aunt Honey
Episode – “Moveable Feast Part 1” – Season 4

A lot of Grace’s family members are mentioned but not seen. We finally get to see the legendary Kazan as Grace’s kitschy aunt, and she tells Karen about how she’s committing adultery: “Let’s put it this way. Everything in this place is broken, but I still call him Super.” Kazan should have been in the show a LOT more than this.

90. Eric Stoltz as Tom Cassidy
Episodes – “Kiss and Tell” and “Friends with Benefits” – Season 7

It sort of doesn’t make sense that Grace would consider hooking up with a married man after Leo’s betrayal, a fact that Jack points out later. Stoltz, however, is charming, and we get this close to some ginger on ginger action.

89. Jack Black as Dr. Hershberg
Episode – “Nice in White Satin” – Season 6

When Will encourages Karen to overcome her fear of doctors, the specialist they see seems…a bit off. Black is only on screen for a few moments (and he wasn’t credited for his appearance), but he makes quite the impression. He even gets to act a little with girlfriend (and Will & Grace consulting producer) Laura Kightlinger as Nurse Sheila.

88. Victor Garber as Peter Bovington
Episode – “Saving Grace, Again (Part 2)

Garber plays a classically trained actor with a chip on his shoulder. As a former television commercial icon (hocking cocoa), Peter is a candidate to appear on a spot for Out TV. When he finds out that they want him to revive his old character and not put his chops to the test, he walks off set. Rip Taylor is excitedly also campaigning for the spot.

87. Katie Couric as Herself
Episode – “Marry Me a Little, Marry Me a Little More” – Season 5

Grace and Leo run into Couric when Today is filming a huge wedding segment in Central Park. Couric is her perky self in the first scene, and then she’s a bit more annoyed at the end when she reveals that the priest wasn’t licensed in the state of New York. It’s not an earth-shattering appearance, but at least Couric gets to bitchily comment on how people expect her to be chipper all the time. This also happens to be the 100th episode of the series.

86. Alan Arkin as Martin Adler
Episode – “It’s a Dad, Dad, Dad, Dad World” – Season 7

While we never have seen Grace’s father until this point, we have heard of him throughout the entire series. He’s lovingly embodied by Arkin even though he constantly gives Grace a hard time and doesn’t notice when she falls out of a speeding golf cart. He’s a great curmudgeon, and him and Debra Messing have some great scenes opposite each other.

85. Joel McHale as Ian
Episode – “Cheaters” – Season 3

Grace is appalled when she catches Will’s father on a date with another woman. When she tells her date, Ian, about her shock, he quickly runs out admitting his own infidelity. McHale gets to yell at some old biddies and tower over everyone in this quick appearance.

84. George Takei as Himself
Episode – “Buy, Buy Baby” – Season 8

Jack’s plan to have legendary actor George Takei on his talk show is thwarted by a conservative takeover of Out TV. While Takei’s appearance is very brief, there are Star Trek jokes abound and an appearance by a talking Takei doll!

83. Lea DeLaria as Nurse Carter
Episode – “Swimming from Cambodia” – Season 6

During Jack’s journey as a student nurse, his energy and charisma isn’t tested until he meets Nurse Carter. She replaces Jack’s favorite teacher in nursing school and doesn’t buy into any of his star student whimsy. Karen intervenes, however, and kidnaps Carter’s dogs in exchange for giving Jack an A in the class.

82. Wanda Sykes as Cricket
Episode – “Buy, Buy Baby” – Season 8

Karen gets jealous of how happy a pregnant Grace is, so she decides to have a baby herself. Instead of trying to get pregnant, she enlists the help of Sykes’ Cricket to carry the child. Sykes can run circles around the normal guest star, and she fits right in with this ensemble. It’s too bad they don’t give her a worthier storyline.

81. Kristin Davis as Nadine
Episode – “Will and Grace and Vince and Nadine” – Season 7

The Sex and the City alum returns to television as “Vince’s Grace.” Will expresses his desire for his relationship with Grace to be more civil, but the niceness in Vince and Nadine’s relationship has a sad undercurrent to it. Nadine is still in love with Vince, and Grace has to set her down to force her to understand that she will never have him. Davis is adorable and sweet as always.

80. Miguel Ferrer as Nathan Berry & Dan Bucatinsky as Neil
Episode – “Saving Grace” – Season 1 / “The Hospital Show” – Season 2

We’ve all gone on a date with a Nathan Berry or a Neil. Will has his share of disastrous dates with slimeballs, and these 2 are the scum of the crop. Ferrer’s Nathan is rich and arrogant, thinking that he can control his Will behaves while Neil is just a privileged creep. Poor Will. Don’t worry, Vince is worth the wait!

79. Shohreh Aghdahloo as Pam
Episode – “Cowboys and Iranians” – Season 8

When Grace is forced to hire a second assistant, she feels guilty about her privilege and hires Aghdashloo’s Pam, an incompetent secretary who happens to be Iranian. It still hurts that Renee Zellweger beat out Aghdashloo for Best Supporting Actress a few years prior to this episode. Aghdashloo doesn’t get to flex her comedic muscles very often, so this is a nice sarcastic showcase for her.

78. Joan Collins as Helena Barnes
Episode – “My Best Friend’s Tush” – Season 2

Early on in the series, Grace mentions that she keeps Karen on as an assistant because she uses her contacts to stay afloat. We don’t see much of that, but Grace is discouraged when the glamorous Collins competes with her for a design job. She later discovers Helena Barnes slathering guacamole all over her face in a Mexican restaurant that caters to uptight socialites. It’s fun to see Collins to full-on bonkers while stuffing her face.

77. Stuart Townsend as Edward AKA Pastry Chef
Episode – “The Fabulous Baker Boy” – Season 7

Will & Grace doesn’t exactly have the best track record when talking about fluid sexuality (don’t be too hard on it–it ran from 1998-2006), but Townsend strutted around this episode as a proud, bisexual baker. When Will advises Karen to fire some of her ridiculously titled staff, he doesn’t expect to have a tryst with Karen’s pastry chef. Edward then turns around and sleeps with Karen before offering to have a threesome with the two them because “we are all sex.” Don’t lie. You’d want to try his macaroons, too.

76. Andy Richter as Dale
Episode – “The Old Man and the Sea” – Season 8

Karen calls out Grace for being a snob when she scoffs at a blind date with Richter’s Dale. Grace tries to prove Karen wrong by going on a second, but then she opens up her big mouth to sing “Being Alive” from Sondheim’s Company. That’s hard to bounce back from…

75. Tim Curry as Marion Finster
Episode – “I Do. Oh, No, You Di-in’t” – Season 6

When Karen and Finster “elope” to Las Vegas for their wedding, it’s a family affair–except for Grace since Debra Messing was off having her child. We meet Finster’s brother, Marion, and you can’t have two Monty Python alums in the same show without a little zaniness. Marion kisses Karen and then his brother within the first 5 minutes of being introduced to him. His trademark smirk is a welcome presence to the Will & Grace family–even if the marriage lasts about 10 minutes.

74. Laura Kightlinger as Nurse Sheila
Best Episodes – “A.I. -Artificial Insemination: Parts 1 & 2” – Season 4

You don’t get more droll and dry than Kightlinger’s delivery as a lazy nurse. She’s most prominent in the episodes where Will and Grace try to get pregnant together, and it leads to this awesome exchange:
Grace: Save little Sheila!
Will: No Sheila. We talked about this. Sheila’s a whore’s name.

Grace: He’s right. Sheila’s a bit whore-y, don’t you think?
Nurse: We haven’t met. Hi, I’m Sheila.

73. Rosanna Arquette as Julia
Episodes – “Women & Children First” and “Fagmalion: Part 1” – Season 5

When Grace marries Leo and moves into his apartment, she befriends the massage therapist that lives in her new building. While the storyline where Grace thinks Julie is coming onto her is really amusing, it’s Julie’s digs at her absent actor husband that make her stand out in her episodes.

72. Jeff Goldblum as Scott Woolley
Various episodes through Season 7

Over the course of 8 seasons, Karen has had her share of romances and adversaries, but none stranger than with Goldblum. Scott Woolley is hellbent on destroying Walker, Inc., but then this devious trickster reveals to have quite the complicated past with our favorite boozehound. It’s hard to think of an actor who would pull off such absurd material, all the while allowing the other characters to continually make fun of how tall and thin he is.

71. Jamie-Lynn Sigler as Ro D’Angelo
Episode -“Queens for a Day” – Season 7

Lesbians get a lot of jokes thrown their way on this show, but there aren’t a lot of coming out stories. During this two-parter, Will is trying to prove himself worthy of Vince to Vince’s mother, but a lot goes berserk this Thanksgiving. One of the competing storylines is that Ro, Vince’s engaged sister, is really gay, and she goes back and forth on whether to come out or not while her entire family is assembled for the holiday. Sigler was playing Meadow Soprano for HBO at the time, but here she gets to play up some different Italian family stereotypes. At least there’s a lot less blood on Will & Grace.

70. Jason Marsden as Kim
Episode – “It’s the Gay Pumpkin, Charlie Brown” – Season 5

Grace is gung ho about going on a bike trip with Leo in the Catskills, but Will wants to stay home and be miserable. When Leo promises to set Will up on a date, he reluctantly agrees to go, but is disappointed when he finds out that Kim is quite short. Jack encourages him to not overlook the south after pocket gay, (“The perfect travel-size homosexual. Just pop him in a man-purse, a briefcase, and you’re good to go. In ten years they’ll be making ’em all that way”), and Will eventually has a good time. We don’t get a lot of opportunities to see Will relax when it comes to romance and sex, and when he sneaks Kim into his apartment later, he gets a very loud response from the live studio audience.

69. Chita Rivera and Michele Lee as Lenore and Lucille
Episode – “Dance Cards and Greeting Cards” – Season 7

On Valentine’s Day, Will and Jack run into this dancing duo at Karen’s country club. They originally introduce themselves as sisters, but Will learns that they only say that because of the club’s homophobic policy against gay members. Instead of running away or continuing to keep it a secret, Will dances with Jack and Lucille and Lenore take the dance floor as a proud out couple. It’s a sweet episode, and who wouldn’t want to see these Broadway divas dancing live?

68. Michael Douglas as Detective Gavin Hatch
Episode – “Fagel Attraction” – Season 4

At the top of the episode, Will’s laptop is stolen at a coffee shop, and the detective assigned to the case is a closeted man who makes up elaborate stories in order to spend time with men. Douglas is surprisingly game, and even grinds on Eric McCormack during “Get Your Freak On” in a dance club scene. You might raise your eyebrows more than laugh, but at least he’s willing to try more comedy.

67. Veronica Cartwright as Judith McFarland
Episode – “Homo for the Holidays” – Season 2

One would think that Jack wouldn’t have to actually come out to anyone since his flame proudly burns bright. And, you know, he talks about boys and butt-robics constantly in the first few seasons. It’s a shock to everyone when he tells everyone that his mother doesn’t know that he’s gay (“What is she, headless?!” Karen asks), and Will demands that Jack tells his mother the truth when she arrives for Thanksgiving. Her reaction is classic: “Looking back on it… There have been clues. When you were a child, you were overly fond of the nursery rhyme “Rub-a-dub-dub, 3 men in a tub.”

66. Candice Bergen as Herself
Episode – “Strangers with Candice” – Season 6

Karen and Candice Bergen in a prank war? Sign us up! With Jack pursuing the noble nursing trade, he tries to put a stop to these women joking each other at a fancy restaurant. It’s not overly original or plausible, but anything that gets Candice Bergen back on our televisions gets a pass in our book!

65. Richard Chamberlain as Clyde
Episode – “Steams Like Old Times” – Season 8

The later seasons of the show find Will struggling to find purpose in his life. Clyde is one of the people who benefits from Project Angelfood, the meals program Will participates with, and he invites the older gay gentleman over for the 10th anniversary of the Suck On it Cup. Since Will is now all about giving, Clyde gets paired up with Grace much to her dismay. His conviction to the wrong answers punctuated with angry outbursts from Grace makes this a game night that no one will be able to forget.

64. Sharon Stone as Dr. Georgia Keller
Episode – “The Blonde Leading the Blind” – Season 7

Will encourages Grace to see his therapist because her aggressive style (which he calls tough love) has been really helping him. He’s taken aback when Grace exits her first session laughing and truly connected with the woman who spends his sessions berating him, but the final straw is when Will tells Grace that he will be a case study in Dr. Keller’s new book. They each try to out-psycho each other which leads to yet another discussion about Will and Grace’s strange bond. Stone is all ice (not icepick) and hard sarcasm here, and it’s fantastic that she isn’t expected to be a sex symbol.

63. Nicollette Sheridan as Dr. Danielle ‘Dani’ Morty
Episode – “24” – Season 5

Co-creator Max Mutchnick always stated that Sheridan was a front-runner to play Grace when the show was originally being cast, and it’s hard to imagine her in the role. Sheridan appeared only once as Leo’s Doctors Without Borders colleague who leaves a seductive letter in Leo’s luggage only to have it discovered by Grace. Before meeting Dani, Leo only referred to her as Dr. Morty, and Grace assumed he was a man and was “and old, blotchy Jew.” Sheridan is perfectly cast: she’s leggy, gorgeous, and intelligent.

62. Ellen Albertini Dow as Sylvia Walker
Episode – “The Young and the Tactless” – Season 3

Karen is terrified for her mother-in-law to find her, but she’s actually embodied by the tiny, sweet Dow. Even though Jack and Will are looking forward to the opening of The Atom Bar, Sylvia ends up going out with the boys when Karen abandons her at Will’s apartment (in what Karen refers to as “government-assisted housing”). Will plucks up the courage to accept the advances of a younger guy, and when he turns to Sylvia for a small celebration, she realizes that everyone around her is gay. She storms out of the bar just like your own grandmother did when she found out that you were gay.

61. Orson Bean and Piper Laurie as Joseph Dudley and Sharon Timmers
Episode – “There But For the Grace of Grace” – Season 2

Will and Grace travel to meet a former professor from college and are shocked that he has become a pessimistic curmudgeon, but they are even more shocked when they realize that Dudley has a “Grace” of his very own. Dudley and Timmers fight like a bitter, old married couple, and Will and Grace become terrified that they will end up like these two since they got into a similar fight on their journey up to meet them. Laurie and Bean have such an acidic hatred for one another that makes you kind of wish you could flash forward and see Will and Grace angry and resentful with one another.

60. Geena Davis as Janet Adler
Episode – “The Accidental Tsuris” – Season 6

Is it too early to demand a Commander in Chief revival?It took six seasons for us to meet Janet, and she’s embodied by a towering, bohemian Davis. Janet comes to New York to launch her jewelry line, but Grace has no faith in her and tosses her out. After a few days, Janet re-emerges as a woman who has everything: a great job, a nice apartment, and fresh new do! Davis excels at playing put-together, strong women (hello, Dottie Henson!), so it’s great to see her messy and sloppy for a change. Anything to keep her away from those Stuart Little movies!

59. Ed Burns as Nick
Episodes – “Dance Cards and Greeting Cards” and “The Birds and the Bees” – Season 7

When you want some real New York authenticity, you grab Ed Burns. Burns plays Nick, a greeting card writer who romances Grace after her divorce from Leo. They meet on Valentine’s Day, and she gives him a hard time for writing Hallmark staples (“I prefer to think of them as very short stories,” Nick tells her). It doesn’t last long, but it’s a nice alternative after Harry Connick Jr. left the picture. There’s something sexily stable about Burns as an option for Grace

58. Demi Moore as Sissy
Episode – “Women and Children First” – Season 5

Moore was such a huge movies staple in the 1990’s, but she gets to play a sillier maternal figure as Jack’s former babysitter who comes back for a new batch of supervision. Jack will always be a kid, and he’s thrilled when he has someone bake him cookies and tell him stories (“Well, I don’t want to be an adult anymore! It’s very hard!” Jack yells to Will). It’s really unlike anything we’ve seen Moore do, but her asking us to use our indoor voices would probably be annoying if she was to come back for more episodes.

57. Dave Foley as Stuart Lamarack
Various episodes – Season 6

Stuart was one of Jack’s most stable relationships–maybe his best? Stuart comes to Will to sell his company, and Will then bribes Jack to go out on a date with him. When the truth comes out, Stuart is hurt, but not as hurt as Jack who finally found a meaningful relationship. It’s one of the only times we see Will encourage Jack to go after a relationship. Foley’s weird charm makes him a great foil for Jack’s ADD-addled exuberance.

56. Will Arnett as Artemis Johnson
Episode – “Back Up, Dancer” – Season 7

No one desperation like Will Arnett. As Janet Jackson’s oldest back up dancer, he goes toe-to-toe against Jack in a dance off to see who will stay on tour with Jackson. It might be the role that Arnett was born to play. Artemis is like the long-lost Bluth family member who happens to be able to dance his face off.

55. Neil Patrick Harris as Bill
Episode – “Girls, Interrupted” – Season 2

Six years before Harris confirmed that he was gay, he played Bill, the leader of a gay conversion group called Welcome Home. Jack sees his picture on a flyer and ropes Karen into playing “former homosexuals” at a local meeting. At first it appears that Bill will only reject Jack’s advances, (“I have to say something here. The back-slapping and the head-rubbing was one thing, but the ear-blowing and the butterfly kisses are not standard NBA practice,” Bill tells Jack after watching a basketball game), but we all know that those groups are total bull. Right, Mr. Vice President? It’s one of the most buttoned-up performances of Neil Patrick Harris’ career.

54. Chris Penn as Rudy
Episode – “Fanilow” – Season 6

Is Rudy one of the only bears featured during the entire run of Will & Grace? That’s a shame. As Barry Manilow’s road manager rejected by Will while waiting in line at a Subway, Penn plays a character that might feel a tad ostracized by the standard Will & Grace audience. While Will is always our uptight and dorky hero, we sometimes forget how shallow he can be. If he gave Rudy an actual chance, maybe he’d find love a little quicker. I mean, Rudy does have lashes for days.

53. Dylan McDermott as Tom
Episode – “Heart Like a Wheelchair” – Season 6

When Will has to take care of his injured mother, he initially think it’s going to be a huge burden. That is until he meets Tom, a gay man who has a passion for turtlenecks, wheelchairs, and taking care of his own mother. Tom seems like a perfect match for Will–they’re both tall, fit, handsome brunettes, but Tom’s devotion for tending to his own mother might make Norman Bates roll his eyes.

52. Andy Garcia as Milo
Episode – “Field of Queens” – Season 5

Karen becomes smitten with a man for the first time since Stan. Garcia’s Milo is a slick restauranteur, and he’s everything Karen dreams of. He’s charming, handsome, and notices her heaving bosom when she comes into his restaurant. Unfortunately, he’s also a player. He takes Karen out and neglects to call her back even though he promised he would. Karen’s hurt is something very new to her since she’s been out of the game for so long, and Mullally really registers her pain in a tender scene between Karen and Grace at the end of the episode.

51. Patrick Dempsey as Matthew
Episodes – “Love Plus One,” “Crazy in Love,” and “Brothers, A Love Story” – Season 3

If anyone was perfect on paper for Will, it was Matthew. They originally have a meet-cute when Jack tries to pick up Matthew first and Will plays Cyrano. When Will and Matthew start dating, however, there’s a huge snag. Matthew, a sportscaster on the rise, is still in the closet, and Will refuses to go back in just for the sake of a relationship. While the connection between them is quite effortless, the character arc highlights closeted gay men in the workplace that no other sitcom has tackled before. Oh, and Dempsey is dreamy. Before he was McDreamy.

What do you think of our first set of guest stars? Did we rank someone too low? Who are you excited to see in Part 2?