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Top 10 Most Memorable Will & Grace Guest Stars

VO: Rebecca Brayton WRITTEN BY: Nick Spake

The stars of Will and Grace ran into some familiar faces over the years. For this list, we’re taking a look at big name performers who made guest appearances on this NBC sitcom. We’ve excluded celebrities who made cameos as themselves because that’s a list for another day. Our list includes Neil Patrick Harris, Ellen DeGeneres, Britney Spears, Alec Baldwin, Matt Damon, and more! Join MsMojo as we count down our picks for the Top Best 10 Will & Grace Guest Stars.

Check out the voting page for this list and add your picks: https://www.WatchMojo.comsuggest/Top%2010%20will Special thanks to our users MikeMJPMUNCH, Stine Pedersen and Looch Incali for suggesting this idea!

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Script written by Nick Spake

Top 10 Memorable Will & Grace Guest Stars


These four leads sure ran into a lot of familiar faces. Welcome to MsMojo and today we’ll be counting down our picks for the Top 10 Will & Grace Guest Stars.

For this list, we’re taking a look at big name performers who made guest appearances on this NBC sitcom. We’ve excluded celebrities who made cameos as themselves because that’s a list for another day.





#10: Neil Patrick Harris as Bill


“Girls, Interrupted”

Six years before officially coming out as a gay man, actor Neil Patrick Harris appeared on “Will & Grace” as the leader of an “ex-gay” support group. Claiming that he has forsaken his homosexual ways, Bill is convinced that he can lead gays down a straight and narrow path. Finding this ridiculous, Jack tries to bring out Bill’s “inner homo” by pretending to be heterosexual. The results are as hysterical as they are enlightening. With some additional help from Karen, the entire group eventually realizes that they’ve been kidding themselves. While Bill could’ve come off as mean-spirited, Harris molds him into someone who’s merely misguided and in denial, and ultimately switches to the winning team.







#9: Glenn Close as Fannie Lieber


“Hocus Focus”

In this episode, Oscar-nominee Glenn Close lampoons Annie Leibovitz as photographer Fannie Lieber. Will and Grace have no idea what they’re getting into when they land a free photoshoot with Fannie, who tears down all boundaries after emerging from behind a curtain. Since they’re never satisfied with their photos, they keep coming back for more insanity. Close does an exceptional job at conveying the erratic nature of a passionate artist who’s constantly flipping between being snarky and completely over-the-top. In addition to delivering the laughs, Fannie also gets up close and personal with Will and Grace, capturing them at their most vulnerable moment.



#8: Ellen DeGeneres as Sister Louise


“My Uncle the Car”

Having already opening up publicly about her sexuality, Ellen DeGeneres was a natural choice to guest star on “Will & Grace.” In an appearance that totally catches the audience off-guard, Ellen pops up as Sister Louise, a nun with a hilariously tragic backstory. In addition to being married to the Lord, she also operates a cheesecake business on the side. So when Grace tries to buy her late uncle’s car back, Louise is unwilling to part with her new delivery vehicle. Talking less like a nun and more like a stand up comedienne, Louise will have you laughing all the way to the zoo. It shouldn’t come as a surprise that this is Ellen’s favorite episode.







#7: Nick Offerman as Nick & Jackson Boudreaux


“Moveable Feast: Part 2” & “Friends and Lover”



Before he was Ron Swanson on “Parks and Recreation,” Nick Offerman appeared on “Will & Grace” as a plumber who has a near-sexual encounter with Karen. Two years after this episode aired, Offerman and actress Megan Mullally would tie the knot in real life. When the series returned for a ninth season years later, Offerman came back as another character named Jackson Boudreaux. A baker who commands every room he enters with intense sexual prowess, Jackson winds up in a relationship with both Will and Grace. Karen, meanwhile, doesn’t find him attractive at all. As absurd as things get, Offerman once again proves that he’s a master at maintaining a straight face.



#6: Matt Damon as Owen


“A Chorus Lie”



From “Good Will Hunting” to “Will & Grace.” Since actor Sean Hayes actually convinced Matt Damon to appear on the show, it’s only fitting that he plays Jack’s charismatic rival, Owen. Both men are in competition for a spot in the Gay Men’s Chorus, but Jack thinks that he has the upper hand upon realizing that Owen is actually straight. Owen puts up a convincing front, even claiming that he has a boyfriend named Ben (get it?), although he has a hard time controlling himself when Grace enters the mix. Despite being crafty, Damon also brings out Owen’s vulnerable side when he finally confesses the truth.





#5: Alec Baldwin as Malcolm Widmark


Various Episodes



In what could be viewed as a predecessor to “30 Rock” character, Jack Donaghy , Alec Baldwin made his debut on “Will & Grace” towards the end of season 7 as Malcolm. Initially approaching Will about a job opportunity, it’s eventually revealed that Malcolm is actually a government agent in cahoots with Karen’s not quite dead husband, Stan. Malcolm and Karen quickly take a liking to each other, commencing an on-again, off-again relationship. Malcolm notably makes a comeback in return season 9 where he rekindles old feelings with Karen. Malcolm's unfiltered mouth, commanding presence, and eccentric nature arguably makes him an ideal match for her.





#4: Michael Douglas as Detective Gavin Hatch


“Fagel Attraction”



Fifteen years after starring in “Fatal Attraction” and almost eleven years before playing Liberace in “Behind the Candelabra,” Michael Douglas appeared on this show as a gay detective with relationship issues. Gavin Hatch might be a confident crime fighter, but he’s incredibly insecure when it comes to dealing with men. He thus cooks up an elaborate ruse to spend time with an oblivious Will. Of course there is one thing that freaks Gavin out even more than being open: a set of teeth covered in cookies. On one hand, you could say that Douglas is playing against type as Gavin. At the same time, his versatility as an actor makes him perfect for the role.





#3: Madonna as Liz


“Dolls and Dolls”

This show is no stranger to hosting pop sensations, featuring appearances from Cher and Jennifer Lopez. What makes Madonna’s guest spot stand out from the others is that she doesn’t play herself. Rather, the Queen of Pop stars as Liz, a “real” office worker who has lived a very unreal life. Liz’s fun-loving personality seemingly makes her a compatible roommate for Karen. Sometimes when you get two extreme egos together, however, it can backfire. A fight over a man instantly turns the two friends into jealous rivals, resulting in Liz being evicted.



#2: Gene Wilder as Mr. Stein


Various Episodes

In his final role before retiring from acting, the late Gene Wilder turned in a Primetime Emmy-winning performance as Will’s boss, Mr. Stein. Nobody plays crazy better than Wilder and the writers took full advantage of his unique talent during his time on the show. Like many of Wilder’s characters, Mr. Stein frequently shifts between being calm and totally unhinged. Sometimes he’ll even turn on a dime mid-sentence. Unlike some of his other characters, though, Mr. Stein has actually spent time in a mental institution and he probably shouldn’t have left. The unpredictable dialog mixed with Wilder’s dead-on delivery make for an unforgettable guest spot, complete with “Young Frankenstein” and “Willy Wonka” references.



Before we get to our top pick, here are a few honorable mentions:



Macaulay Culkin as Jason 'JT' Towne

“May Divorce Be with You”





Britney Spears as Amber-Louise

“Buy Buy Baby”




Molly Shannon as Val Bassett

“Girls, Interrupted”





#1: Debbie Reynolds as Bobbi Adler


Various Episodes

It’s made abundantly clear throughout the series that Grace isn’t exactly an angelic singer. What makes this all the more hilarious is that Grace’s mother is played by one of the greatest musical talents of all time, Debbie Reynolds. Needless to say, Bobbi Adler’s voice was easier on the ears than Grace’s. As this recurring character, Reynolds portrayed a parent who could be overbearing and judgmental, but also came off as warm and nurturing. Even when their relationship hit a bitter note, Bobbi and Grace would always get back on tempo. Reynolds sadly passed away shortly before the revival, although the cast and crew didn’t forget to pay their respects to this unparalleled guest star.

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