Ranking 101 Will & Grace Guest Stars: Part 2

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

We continue out countdown of the 101 Will & Grace guest stars with the top 50. You will find plenty of Broadway divas and recurring guest stars on this section of the list. If you think we forgot anyone, sound off in the comments below. If you need to play catch up, you can find the first entry here.

50. Sara Gilbert as Cheryl
Episode – “Fanilow” – Season 6

When Will waits in line for Barry Manilow tickets, he meets “The leader of the Fanilows,” Cheryl. Gilbert offers her trademark heavy-lidded delivery, and you actually believe she spends most of her days pining for the beloved singer.

49. Nick Offerman as Nick
Episode – “Moveable Feast Part 2” (sometimes billed as a one-hour episode titled, “Thanksgiving”) – Season 4

One of the best things about your girlfriend being on a hit sitcom is that it can sometimes lead to awesome side gigs! Before Offerman became a regular on Parks & Recreation, he did a small gig as a plumber who becomes the object of Karen’s lust. Her husband, Stan, gives her permission to sleep with other men, but Karen struggles to decide whether she wants to do it. Offerman was dating Mullally at the time, and they were married in 2003.

48. Janet Jackson as Herself
Episode – “Back Up, Dancer” – Season 7

Apparently Ms. Jackson can’t make up her mind. When Jack becomes her latest back up dancer, she keeps changing how many dancers she actually wants on her newest tour. Will Arnett and Jack must battle it out for the coveted spot, but Jackson gets points for just joining one of our favorite shows. She does get an amazing entrance in her first scene.

47. Tracey Ullman as Ann
Episode – “Looking for Mr. Good Enough” – Season 6

I’ve actually always wanted to take a cooking class, but I know I’d be bummed if Ullman wasn’t teaching it. Will, Jack, Stuart, Joe, and Larry take a cooking class, but they don’t know it’s really for couples, leaving Will to prepare everything alone while everyone loudly comments on it. Ullman takes a thankless role and makes it silly by being a cooking teacher who is proud of her prosthetic finger (“Sometimes I throw it in the dishwasher!”)

46. James Earl Jones as Himself
Episode – “Me and Mr. Jones” – Season 6

Have you always dreamed of watching the legendary James Early Jones read dialogue from Sex and the City? Well, look no further! Jack lands a role in a production of The Iceman Cometh with Jones, but the director only praises Jack’s acting. Jones decides to take Jack’s acting class to get back to his roots, but Jack thinks he should find “the James Girl Jones” and has him read scenes as Samantha from Sex and the City. The voice of Darth Vader and CNN, Jones hasn’t really done anything like this in his career. Try getting his high-pitched voice screaming “Jimmy Choo!” out of your head. You can’t.

45. Reed Alexander as Jordy Truman
Episodes – “A Little Christmas Queer” and “The Mourning Son” – Season 8

Alexander was only one two episodes late in the series, but he made a big impression with his hutzpah and verve. Will and Jack help Will’s flamboyant 10 year old nephew, Jordy, put on a Christmas show even though his mother, Marilyn, was never supportive of Will’s childhood pageantry. Jordy is an assured little boy, and he doesn’t mince words about performing (he makes his father listen to the RENT soundtrack on loop the entire ride there). To quote Jack upon meeting Jordy: “I…love him!!!”

44. Camryn Manheim as Psychic Sue
Episode – “Gypsies, Tramps, and Weed” – Season 3

We all need a little more Camryn Manheim in our lives, am I right? Manheim guest starred on one episode as a psychic who predicts that Will will spend his life with a man named Jack, sending Will into a tailspin about his love life. Her sing-song attitude is quite reminiscent of her role in Romy & Michele’s High School Reunion.

43. Natasha Lyonne as Gillian
Episode – “Girl Trouble” – Season 3

In the early 2000’s, Lyonne was everywhere. She was in countless movies, but one of her best roles was as Grace’s design intern who falls in love with Karen’s lazy lifestyle. We don’t get to see Grace do a lot of designing (even though we spend tons of time in her office), but Messing lets the inner geek come out in this episode. Lyonne’s transformation from ideal protege to Karen’s spawn makes you think she’s going to pull up another assistant desk and not answer phone calls right along Karen.

42. Mira Sorvino as Diane
Episode – “Last Ex to Brooklyn” – Season 6

When Leo invites his ex-girlfriend Diane to come over for dinner with him and Grace, he doesn’t expect her to the only woman that Will has ever slept with. This is a personal favorite of mine, because everything goes haywire in this episode, and everyone is allowed to go a little bonkers. Things start off well between Diane and Grace: “You’re a gorgeous redhead, I’m an adorable blonde. But we know we have something in common: brown hair.”

41. Ellen DeGeneres  as Sister Louise
Episode – “My Uncle the Car” – Season 3

Will sells Grace’s beat-up old car, but then she wants to buy it back. Doing so proves to be a little tricky when the new owner is a stubborn (but very sweet) nun who needs it to sell cheesecakes. If her Dory catchphrase “Just keep swimming” is her most quoted catchphrase, I’m sure her “We’re going to the zoo” is a close second.

40. Macauley Culkin as J.T. Towne
Episode – “May Divorce Be With You” – Season 6

Transitioning from child actor to adult stardom is quite tricky, but you can succeed if you play against type. When Karen learns that Will cannot represent her in her divorce proceedings against Stan, she hires a young kid who allegedly got Debbie Harry a huge settlement. J.T. actually manipulates Will into giving him everything he needs to win the case, and it turns out he’s a dirty little stoner boy. I’m not sure if viewers were prepared to hear Kevin McAllister say, “Get yourself a bikini wax. I like a clean workspace.”

39. Wendie Jo Sperber as April
Episode – “My Fair Maid-y” Season 1

Will & Grace didn’t have a lot of guest stars in the first two seasons, but Sperber’s maid is the most memorable. Grace gets down on herself when she prepares for a big design showcase, and Will and Grace’s new cleaning woman guides her to enlightenment by screaming in her face and just telling to shut up and do the work.

38. Edie Falco and Chloë Sevigny as Deirde and Monet
Episode – “East Side Story” – Season 6

The Flipping Dykes sounds like a show that HGTV would have greenlit. When Will and Grace start flipping houses, they get competition from a powerful lesbian real estate couple played by Falco and Sevigny. Will comes up with a plan to divide and conquer them, but it turns out these ladies have the same idea for them. Falco capitalizes on her strong presence and Sevigny is delightfully ditzy.

37. Lily Tomlin as Margot
Episodes – “Partners” and “Forbidden Fruit” – Seasons 7 and 8

Tomlin can elevate anything handed to her, and Margot is one of the most eccentric side characters of the later seasons. She’s very up front and direct, and Tomlin is one of the few openly gay actors to appear on the show. You don’t want her as a boss.

36. Christine Ebersole as Candy Pruitt
Episode – “Poker? I Don’t Even Like Her” – Season 3

Karen wants to have bigger shoulders, but she doesn’t know if she wants to submit herself for the experimental surgery. She tricks her old rival Candy into getting them first just to see how they look. Broadway legend Ebersole has a smile plastered on her face almost the entire episode as if a Botox specialist forgot how much he was filling in her face. This role was originally supposed to be Helena Barnes, but Joan Collins turned down the opportunity to reprise her role.

35. Bebe Neuwirth as Herself
Episode – “No Sex ‘N’ the City” – Season 6

Jack and Karen are so distraught over Friends and Frasier ending that they can’t even find new life experiences for themselves. When Bebe Neuwirth comes into their local coffee shop, they almost literally take her hostage in order for her to say lines as her Frasier character, Lilith. We don’t get to see her o n screen very often anymore, so we need to soak in every performance she gifts us with.

34. Britney Spears as Amber-Louise
Episode – “Buy, Buy Baby” – Season 8

The Princess of Pop stops by to play the new co-host of Jack Talk, much to Jack’s chagrin. Even worse is that Out TV is bought by a conservative conglomerate attempting to make everyone support George W. Bush, but Amber-Louise is secretly a lesbian just trying to climb the entertainment ladder. Does anyone else think that that could happen in Trump’s America?

33. Rosie O’Donnell as Bonnie
Episode – “Dyeing is Easy, Comedy is Hard” – Season 4

TV’s former Queen of Nice pops up after Jack allows his son, Elliot, to dye his hair blonde. His mother, Bonnie, angrily confronts Jack, but he thinks she has a problem with him being gay and hanging out around her son. She later confesses that she lashed out at him because she’s also gay, and she’s terrified of coming out to him. O’Donnell came out of the closet shortly after her guest appearance, and then she played a similar character on Showtime’s Queer as Folk.

32. John Slattery and Steven Weber as Sam Truman
Episodes – “Big Brother is Coming,” “A Little Christmas Queer,” “The Mourning Son” – Seasons 1 and 8

This is the Darren Stevens of this NBC sitcom. Slattery played Will’s estranged brother in a two-part episode early in the first season, and he ended up sleeping with Grace. In the last season, however, he was replaced by Weber (conflicts with AMC’s Mad Men, we assume?) when he returned to rekindle the flame with Grace in the final season. If the show had continued its original run, Sam might have been a decent fit for Grace. We’ll never know…

31. Taye Diggs as James
Episodes – “Von Trapped,” “The Definition of Marriage,” and “Grace Expectations” – Season 8

Some would argue that James was Will’s hottest romantic prospect, but I personally reserve that title for another of Will’s beaus. Will meets James in probably the gayest meet-cute of all-time. Will is meeting Grace for the Sound of Music Sing-a-Long, but he goes to the wrong theater. James is about to step into a showing of Memoirs of a Geisha. Almost everyone comments on how good-looking Diggs is during his arc (“Mismatch!”), and he even marries Grace to stay in the country. Don’t feel too bad for James, though. It turns out he’s just an asshole in a very beautiful, muscled package.

30. Patti LuPone as Herself
Episode – “Bully Woolley” – Season 7

There is an entire storyline where Jack is stealing locks of hair from Broadway actress to create a wig. Yes, I’m serious. The last person he needs is Patti LuPone, and SHE SINGS DON’T CRY FOR ME ARGENTINA!!! Talk about a Rainbow High!

29. Elton John as Himself
Episode – “The Honeymoon’s Over” – Season 5

Jack is convinced that The Gay Mafia is after him after he kicked out a student from his acting class, and he scrambles to get back into good graces the entire episode. Will shoves him off the entire time, but then comes face-to-face with the Don himself at the end of the episode. John’s appearance is very, brief, but well worth the wait.

28. Bernadette Peters as Gin
Episode – “Whatever Happened to Baby Gin?” – Season 8

In the next to last episode of the series, we find out that Karen has a sister (apparently every time she says ‘gin’ she didn’t mean the drink), and it’s a fun send-up of the cult classic, Whatever Happened to Baby Jane? Karen needs to conserve money, and she tries to tell Gin that she can’t support her anymore. When Karen and Gin were kids, Gin was in a Twister-related accident when Gin and Karen played in a “rickety old saw mill that juts out over the falls” and Gin fell through the floorboards. Peters doesn’t get to sing at all during the episode, but she does get to dance a little. She also makes an insanely dramatic entrance every time she “hobbles” into a room.

27. Dan Futterman as Barry
Episodes – “Fagmalion: Parts 1-4” – Season 5

Sometimes Will can forget what it’s like to come out of the closet. He’s so jaded that he cruelly reject Futterman’s Barry because he dresses badly and has an bushy beard. Since Barry is Karen’s cousin, she offers to bankroll an operation for Will and Jack to do the ultimate makeover in time for the annual Human Rights Gala, and Will falls for Barry in the process. Futterman is sweet and unexpectedly funny, and the My Fair Lady jokes just keep on coming.

26. Suzanne Pleshette as Lois Whitley
Episodes – “Someone Old, Someplace New,” “Something Borrowed, Someone’s Due,” and “Looking For Mr. Good Enough” – Seasons 4 and 6

Jack discovers that Karen’s mother is actually alive when he films a documentary about Karen’s life for her birthday, and he is bent on reuniting them as the ultimate gift. Lois used to drag Karen from town to town pulling cons on innocent people, and she eventually ropes Karen in to do one more job. The raspy-voiced Pleshette bounces well off of Mullally who finds herself in a vulnerable position every time her character appears.

25. Jennifer Lopez as Herself
Episodes – “I Do. Oh, No, You Di-int” and “FYI: I Hurt, Too” – Seasons 6 and 7

Jennifer Lopez is a celebrity who has some of the most fun playing herself on Will & Grace. She originally pops up to poke fun at how overworked she is when she sings at Karen and Finster’s wedding, and Jack becomes one of her back up dancers. J. Lo or Jenny from the Block was constantly in the tabloids for her marriage to Ben Affleck and she even comments on her love life when she gives a toast at the wedding: “Congratulations, Karen and Lyle. And just remember, the secret to a happy marriage is… Ah, who am I kidding? Thank you. Good night.”

24. Sydney Pollack as George Truman

Will considers his father his hero, and they seem to have one of the healthiest father/gay son relationships on television. George serves as an example of how we come to terms with realizing that our parents aren’t perfect. Will discovers that his dad is cheating on his mom and finds out that he never told his co-workers that Will is gay (George eventually makes it right). One of the biggest surprises of the series is the fight between George and Will where George tells Will that he wish he wasn’t gay, and George suddenly dies afterwards. It’s one of the biggest emotional turning points for McCormack.

23. Parker Posey as Dorleen
Episodes – “Loose Lips Sink Relationships” and “Jingle Balls” – Season 4

I’m surprised more drag queens haven’t adopted Dorleen’s persona for performances. Jack is a hellish employee to have on staff, so it’s only fair that he have a verbally-abusive, bitchy, chain-smoking boss at Barneys New York. Jack first deceives Dorleen into thinking Will is interested in her in order to get time off of work for a Caroline in the City acting showcase, and then she grants him the opportunity to design a window during the Christmas season (“You have 24 hours to get this right, or not only will I fire you; I will rehire you, pull your hair, and fire you again!“) . It’s kind of like everyone else abandoned the 80’s coke scene, and no one managed to tell her. Why isn’t she more of a gay icon?

22. Michael Angarano as Elliot

Even though Elliot is Jack’s son, he is everything that he isn’t. He’s kind, considerate, and rather quiet. His presence adds an unexpected layer to Jack’s character, but his performance feels distinctly authentic. He’s adorably lost in a lot of episodes, but he is a great straight man to the zaniness that always surrounds him.

21. Gregory Hines as Ben Doucette

Ben Doucette is a man that doesn’t take no for an answer, and it leads to an unexpected romance with Grace. He approaches romance the same way he does his business, and he usually gets what he wants. When Grace tries to break up with him, he firmly just says, ‘no’ and walks away. Hines and Messing do have a cute, soft, sparring chemistry, and no guest appearance with Hines would be complete without a tap dancing number.

20. John Cleese as Lyle Finster

Karen’s rivalry with Lorraine Finster leads to a romance with her father. At first she sleeps with him for revenge, but she develops actual feelings for him. It’s not all beating hearts and romance since Finny has a knack for talking in dirty sexual innuendos, and Karen can certainly enjoy his massive wealth. All the dirty, raunchy sex doesn’t equal to a happy marriage, however, and Karen announces she wants a divorce at their reception. At least there’s booze for everyone to drink!

19. Glenn Close as Fannie Lieber
Episode – “Hocus Focus” – Season 4

When you want a guest star to be as manic as can be, you hire Glenn Close. As photographer Frannie Lieber (probably the most obvious nod to another living person…), Close photographs Will and Grace for an upcoming family coffee table book. During their first session together, the “recovering drug addict” kisses Will on the mouth and unzips her pants before happily dry humping her. Casting someone like Close means you can go for broke. And she took advantage of it.

18. Gene Wilder as Mr. Stein
Episodes – “Sex, Losers & Videotape” and “Boardroom and a Parked Place” – Season 5

There’s something simultaneously sad and awkwardly funny about Will’s boss, Mr. Stein. He returns from the London office after Ben Doucette retires, but we learn later that he actually was spending time in a mental institution. Will becomes his guide as he shuffles around the office, and he eventually starts a fling with Karen. Wilder is unpredictable in the role. You never know if he’s going to start sobbing uncontrollably or just fire one of his colleagues.

17. Eileen Brennan as Zandra

I bet it was hard for Zandra to cash Jack’s acting class checks since he’s such a horrible student. As his insulting, chain-smoking drama teacher, Brennan is always an inch from exploding at Jack when he turns in half-assed work in her acting classes. It’s a shame that one her last main storylines revolved around Zandra leaving the apartment she always had in Manhattan to live in an actors retirement village. She was rightfully nominated for an Emmy for her work in 2004.

16. Alec Baldwin as Malcolm

Before Will & Grace, Baldwin had only done a few arcs on television (I see you, Knot’s Landing), but he’s quite at home as the mysterious man who helps Will at a government job. Malcolm lures Will to work for a vague charitable organization, and we don’t get a lot of answers at first. It takes a few episodes to discover that Malcolm actually helped Stanley Walker fake his own death but that doesn’t deter Malcolm from trying to get into Karen’s pants.

15. Madonna as Liz
Episode – “Dolls and Dolls” – Season 5

Ok, ok. Is Queen Madge the best actress? No, and she still gets flack for some of her earlier film roles to this day. Liz says she’s in the music business, but she really is an office manager for a company that puts together those cheesy compilation CD’s that you could order off of your TV. Liz and Karen become roommates when Karen decides to get out of the mansion to gain more life experience. Liz got the apartment so her and her boss could continue their affair, but he “got murdered” so she needed someone to move in. Madonna hasn’t played a “real person” since Desperately Seeking Susan, so we shall accept this as gay atonement for The Next Best Thing.

14. Kevin Bacon as Himself
Episodes – “Bacon & Eggs” and “The Finale: Part 1” – Seasons 5 and 8

It feels like Jack has posters of Kevin Bacon in every bedroom we see him in. Not only does Bacon play up a cheap character version of himself, but he gives us what we want: a Footloose dance break.

13. Lesley Ann Warren as Tina

It is hard to play a ditz or a bimbo and not have it get tired or annoying. Warren has been playing roles like this her entire career, but Tina forces us to ask: does ‘the other woman’ have feelings? Will’s father, George, keeps going back to Tina, and Marilyn Truman begins to like their arrangement after a while. The sounds that come out of Warren’s mouth are insane and difficult to replicate. Warren should have been nominated for her performance. Shame on you, Television Academy!

12. Minnie Driver as Lorraine Finster

Lorraine could be written off as a traditional gold digger, but she’s so much more than that. She met Stanley Walker while working in the cafeteria at the prison where he was incarcerated, and they quickly started having an affair. If that wasn’t enough of an insult to Karen, Lorraine tried to steal Jack away from her (but to be fair, Jack was attracted to the Walker bank account), and then Lyle admitted that she was born with both boy and girl parts and decided to raise her as a girl. Driver’s harsh cockney accent recalls if Eliza Doolittle was drunk and fell off of a pier.

11. Harry Connick Jr. as Dr. Leo Markus

This may sound like a controversial, but Leo is the least deserving of all of Grace Adler’s suitors. When Connick Jr. started his arc on Will & Grace, there were a lot of people who said the show jumped the shark because it pulled focus from the dynamic of the central best friends. Leo coming into Grace’s life only strengthened the bond between Will and Grace, because he was able to hurt her in a way that Will never could.

10. Tom Gallop and Leigh-Allyn Baker as Rob and Ellen & Jerry Levine and Tim Bagley as Joe and Larry

These friends are oftentimes forgotten when talking about the greatness of Will & Grace. Rob and Ellen endure most of the scorn from our friends, but Joe and Larry have to put up with a lot of crap from them too. While they may not have huge storylines devoted to them all the time, we should enjoy their company and appreciate how much crap they took for 8 full seasons.

9. Blythe Danner as Marilyn Truman

Mothers are a huge theme throughout the run of Will & Grace, but no mother evolves more than Will’s mother, Marilyn. In the hands of veteran actress Blythe Danner, Marilyn is the poster child for WASP-y New England living. Even though sha has a knack for saying selfish things to the guests that walk into her home, she has learned a lot about being a good mother to her openly gay son. In the final season, she admits that wants to be a better person to her grandkids than she was with Will because she didn’t know how to cope with his coming out. Danner is always a classy woman, and Marilyn is one of her best roles.

8. Sandra Bernhard as Herself
Episodes – “Swimming Pools…Movie Stars” and”Someone Old, Someplace New” Seasons 3 and 4

When Will and Grace find out that cabaret singer Sandra Bernhard is hosting an open house of her apartment, they want to just check out her medicine cabinet and bathroom. They don’t expect to become so chummy with her that Will bids $1 million in order for the celebrity magic to continue. When the truth comes out, she lets out a barrage of swears that can only be attributed to Bernard’s no-nonsense persona.

7. Molly Shannon as Val

If you want crazy, Molly Shannon will deliver you some grade-A nutjob. In her first appearance as eccentric neighbor Val, she becomes a substitute Grace for Will, and she’s pretty buttoned-up for the most part. You can see the crazy trying to leak out, but she keeps shoving it back in. But with each new guest episode, she lets loose more and more. She goes Alex Forrest on Jack after seeing his one-man show, steals a family heirloom of Grace’s, and even tries to take over Grace’s design business. In a lot of scenes you can see Messing trying not to laugh, and it’s a feat that they got through the episodes at all, because Val is so unpredictable.

6. Bobby Cannavale as Vince D’Angelo

Vince is a perfect match for Will because he calls him on all of his crap. Coming from a traditional Italian family, Vince’s main problem is that he can’t pass up an opportunity to try on gloves or accessories when he’s on duty as a cop. Sure, some people get injured in the line of…fashion…but he’s a dreamboat with a big heart. Not only is he handsome and dorky, but he brings out the best of Will. When Vince loses his job, Will has to learn how to be a supportive partner and put aside his judgement. And, yes, he looks damn good in uniform.

5. Woody Harrelson as Nathan

Grace isn’t consistent when it comes to picking ment to date. She left Danny at the alter, and one of her first relationships after that was with lawyer Ben Doucette. Her next major love interest in Harrelson’s Nathan. They instantly don’t get along (he takes her wet laundry out of a washer without her knowledge and then she criticizes how he plans to woo an ex-girlfriend), but they do say opposites attract. At this point in the series, you could even say that Grace needed someone like Nathan to change her perceptive of her expectations of love and marriage. Nathan is simple-minded, loving, and the best fit for Grace. There. I said it.

4. Matt Damon as Owen
Episode – “A Chorus Lie” – Season 4

In one of the most theatrical episodes of the entire show, Oscar-winner Matt Damon plays a straight guy who infiltrates the New York City Gay Men’s Chorus. When Jack sees him checking out a woman, he sets his sights to destroy Owen for trying to take a spot in the coveted singing group. This is a near-perfect episode: an overly horny Grace, Jack and Matt Damon singing “Let’s Hear It For the Boy,” and references to both Anne Heche and VH1 Divas Live. Owen even says that he has a high school boyfriend named Ben.

3. Cher as Herself
Episodes – “Gypsies, Tramps, and Weed” and “A.I. – Artificial Insemination: Part 2” – Seasons 3 and 5

Even though Cher only appears in 2 episodes in the entire series, her presence is felt throughout. It’s probably because Jack constantly does impressions of her and the Cher doll is featured throughout the show. It’s fitting that she appears as a godlike figure in her second appearance (in a dream sequence where she hijacks the spotlight to hock some albums), because the gays would worship her until the end of time. Cher could appear as an extra in the background and still make the top of our list, because she’s one of the first huge celebrities featured on the show.

2. Leslie Jordan as Beverly Leslie

Leslie Jordan finally won an Emmy for his role as pint-sized Beverly Leslie in the final season. He’s everyone’s enemy, but most routinely squares off against Karen and Jack during the series. Even though he’s “not gay” we usually find him swishing into scenes to cause a ruckus before sashaying back out again and delivering a snappy quip on his way out of the room. Jordan’s soft, Southern drawl and bitchy ‘tude make him the ultimate adversary mainly because he’s so obnoxious. You just want to flick him out of the room. He’s absolute perfection.

1. Debbie Reynolds as Bobbi Adler

The late, great Debbie Reynolds tops our list, because she’s the ultimate entertainer. Even though Grace complains that her mother hogs he spotlight and demands too much attention, she’s lovable all the while. Maybe because she’s not our mother? If you watch Reynolds’s first appearance in the debut season, she brings an old school verve that’s absolutely hysterical. Grace and Bobbi clashed so much because they were so much alike, something that Grace admits but is reluctant to accept. Deep down, Bobbi is a loving mother. The recent loss of Reynolds is going to make the revival hurt so much when she doesn’t barge into a room singing at the top of her lungs.