The Most Overqualified Guest Star Performances On '90s Sitcoms

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Vote up the performers who made surprising appearances in '90s comedies - and nailed it.

Many actors have gotten their first big break by taking a guest spot on a television series. But another established tradition is the one of famous actors and other celebrities agreeing to make guest appearances. Friends, The Simpsons, and That '70s Show are just a few of the shows that have been able to boast of snagging multiple stars for guest roles. 

Although the majority of these guest appearances have been one-offs, there have been a few, such as Mary Tyler Moore's three-episode arc on That '70s Show, that were expanded beyond one episode. And occasionally, as with Jean Stapleton's performance as Brett Butler's eccentric aunt on Grace Under Fire, these roles have earned the guest star an Emmy nomination.

Here are some of the more notable celebrities who one might be surprised to learn appeared as guest stars on television comedies.

  • Ray Charles Appeared In Four Episodes Of 'The Nanny' As Yetta's Boyfriend Sammy
    Photo: CBS

    The Nanny  was another 1990s sitcom that utilized many famous celebrities in guest star roles. Most of these appearances were one-off appearances, but in the show's fifth season, legendary musician Ray Charles appeared in four episodes as Sammy Jones, the boyfriend - and later husband - of Fran's grandmother.

    It was the first time that Charles had played anyone other than himself in a sitcom. The Nanny star Fran Drescher was the one who approached Charles about taking on the role and was very excited when the musician accepted the offer.

    His first appearance on the show was in the first episode of Season 5, "The Morning After."

  • On 'Friends,' Julia Roberts Played Chandler's Former Grade School Friend Who Wants To Date Him - For A Secret Reason
    Photo: NBC

    Julia Roberts made a guest appearance on Friends during the sitcom's second season playing Susie Moss, a former classmate of Chandler's (Matthew Perry) in the episode titled "The One After the Superbowl."

    In the episode, Roberts's Moss (a makeup artist) runs into her old schoolmate on a movie set and reminds him about how she was christened "Susie Underpants" after he lifted her skirt up as a prank one day when they were in fourth grade. He apologizes and they begin dating. One night, she talks him into wearing her underpants at dinner - then leaves him stranded in the restaurant's men's room clad only in those panties after stealing his clothes. Ah, revenge!

    At the time of this guest appearance, Roberts wasn't just one of the biggest movie stars in the world - she also had twice been nominated for an Academy Award for her performances in the films Steel Magnolias and Pretty Woman.

    In an interview with The Hollywood Reporter, Kevin Bright, one of the co-creators of Friends, recalled that Matthew Perry was the one who reached out to Roberts about being on the show:

    She wrote back to him, "Write me a paper on quantum physics and I’ll do it." My understanding is that Matthew went away and wrote a paper and faxed it to her the next day.

    Although Roberts's character may have been faking her romantic interest in Chandler just to get revenge, there clearly was real chemistry between the two actors; Roberts and Perry dated briefly following her appearance on the show.

  • On 'That '70s Show,' Bruce Willis Played A Sleazy Security Guard For An Exclusive Club
    Photo: Fox

    In 2005, Bruce Willis appeared as a guest star on That '70s Show, playing the sleazy head of security at the Playboy Club in the episode entitled "Misfire."

    In the episode, Michael Kelso (Ashton Kutcher) travels to Chicago to visit his daughter and ends up at the Playboy Club, where he has an interview with Vic (Willis) about the possibility of Kelso getting his "dream job" of being a bouncer at the club. During the interview, Vic admits to spying on the Playboy bunnies through a peephole in his office and not wearing his wedding ring so the women working there won't know that he's married.

    Willis had gotten his first huge break as an actor on television, starring in the romantic crime comedy-drama series Moonlighting opposite Cybill Shepherd from 1985 to 1989 before the blockbuster film Die Hard (1988) propelled him to movie stardom.

    It was Kutcher who asked Willis to appear on the sitcom. The two men were close friends, despite the awkwardness of the former having married to the latter's ex-wife (Demi Moore) around the time of Willis's appearance on That '70s Show. Willis was not paid for his guest spot, instead donating his salary to the American Red Cross Disaster Relief Fund in order to help the survivors of Hurricane Katrina.

  • On 'Friends,' Joey Falls For A Crazed Fan Played By Brooke Shields
    Photo: NBC

    Julia Roberts was just one of several guests stars to appear in "The One After the Superbowl" episode of Friends. Brooke Shields portrayed a mentally ill fan who believes Joey (Matt LeBlanc) actually is Dr. Drake Ramoray, the character he portrays on the soap opera Days of Our Lives. Joey goes out with her, but she ends up accusing him ("Drake") of cheating on her. When she refuses to believe he's only an actor, his friends convince her that he isn't Drake, but his evil twin. This results in her leaving Joey alone.

    Shields had shot to fame as a child model before earning acclaim for her performance in the 1978 film Pretty Baby. She was performing on Broadway in a revival of Grease when she got a call asking if she had any interest in being on the sitcom. As she told The Hollywood Reporter:

    [I] said yes before I even knew what the part was because they said, "Would you be in the Super Bowl episode?" I was sort of obsessed with the show. There was no way I wasn’t going to do it.

    Series co-creator Marta Kauffman told THR, "Brooke Shields hit it out of the park. She surprised us."

    Warren Littlefield was the president of NBC Entertainment at the time. He was so impressed with a rough cut of Shields's performance that after talking to Friends' showrunners about how she'd been to work with, he reached out to the actor's representatives to say he wanted to do a sitcom with her (Shields ended up starring in the NBC sitcom Suddenly Susan).

  • On 'The Fresh Prince of Bel-Air,' Sherman Hemsley Played Uncle Phil's Rival Who Ruthlessly Campaigns Against Him
    Photo: NBC

    Sherman Hemsley became a television star in the 1970s when he played George Jefferson, an ambitious, opinionated, bigoted, hardworking owner of a chain of dry-cleaning stores, on the CBS hit sitcom The Jeffersons. In 1984, Hemsley was nominated for the Primetime Emmy Award for best actor in a comedy series for his portrayal of Jefferson.

    In 1992, Hemsley was cast as Judge Carl Robertson on The Fresh Prince of Bel-Air. Robertson was the former mentor turned rival of Will's Uncle Phil (James Avery). Hemsley first appeared as Judge Robertson in the episode "P.S. I Love You," an episode in which Uncle Phil decides to run against Robertson for the latter's judge position. In "Here Comes the Judge," Uncle Phil learns that his former mentor is willing to play dirty in order to win the election; indeed, in Hemsley's last appearance as the character (in "Asses to Ashes"), Robertson starts a smear campaign against Uncle Phil, accusing the latter of being a corrupt lawyer who helps get criminals off. 

    Uncle Phil refuses to play dirty and ends up losing the election. When Will goes to confront Robertson about his treatment of his uncle, Robertson suffers a fatal heart attack (after Will tells him to "drop dead"). The governor then appoints Uncle Phil to fill Robertson's now-vacant judge seat.

    Hemsley later appeared on two episodes of The Fresh Prince of Bel-Air as George Jefferson.

  • On 'Seinfeld,' Marisa Tomei Gets Pursued By George Even Though He's Engaged
    Photo: NBC

    During its run, Seinfeld had a number of well-known actors make cameos on the show. That included an appearance on the 1996 episode "The Cadillac" in which Oscar-winning actor Marisa Tomei portrayed herself.

    In the episode, George (Jason Alexander) is told by a friend of Elaine's that she is friends with Tomei and knows that the actor is attracted to funny, quirky, bald men like George. Even though he is already engaged to another woman, George harasses Elaine's friend into giving him Tomei's phone number. The actor agrees to go on a date with him, but when he tells her he is engaged, she punches him in the face and walks away.

    Tomei won the Oscar for best supporting actress for her performance as Mona Lisa Vito in the 1992 comedy film My Cousin Vinny. She was excited to be asked to do a cameo on Seinfeld, as it was the top-rated sitcom at the time. In a 2016 interview with Marie Claire, Tomei revealed why the show reached out to her:

    I just got so lucky that they asked me to participate. I think it didn't even have anything to do with me specifically, they just liked the way my name sounded. Because when I got there I did ask Larry David, "How did I get so lucky? How am I here?" He just said, "Well, when you say your name over and over, it just has a really strong rhythm: 'Marisa Tomei. Marisa Tomei.'"