10 Funniest Celebrity Guest Appearances

Danny DeVito, Gary Oldman and Susan Sarandon in a split image from Friends

First airing in 1995, the American sitcom Friends has remained a firm favorite for fans, with six main characters all different in personality and style. Alongside Monica, Joey, Ross, Rachel, Chandler, and Phoebe, the show was abundant in celebrity guest appearances, ranging from George Clooney to Helen Hunt.

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Including new characters with small parts, that well-known actors played gave Friends an added layer of excitement and often took the storyline in a new direction. While the core characters were always a delight to see on screen, new faces were always welcome, especially when they arrived with good humor and were unexpected roles.



10 Julia Roberts

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As a sitcom that had many unexpected celebrity cameos, Friends added to their ongoing list with Julia Roberts. She played Susie Moss, an ex-classmate of Chandler’s. The pair decided to date each other, but Chandler didn’t realize Susie’s reasoning was to seek revenge on him for exposing her underpants in front of their class years ago.

Roberts’ charm is exuded in her portrayal of Susie, which draws Chandler in. However, she was just as capable of showing the bitterness felt by Susie. The combination of her quick thinking and Chandler’s bafflement made for another funny subplot.

9 Ben Stiller

<!–[if IE 9]> <![endif]–>Ben Stiller guest starring as Tommy in Friends

Most of actor Ben Stiller’s best movies involve comedy, and while his role as Tommy was still full of humor, it also showed Stiller’s ability to deliver an angry and somewhat unpleasant part. Tommy entered the show when he began dating Rachel.

Unbeknownst to Rachel, however, he had a very fiery personality that he didn’t let her see, even when Ross tried to point it out. Tommy’s outbursts were unnerving, but sidesplitting for audiences. Adding to the humor, Ross’ reactions were always a great contrast and timed impeccably.

8 Isabella Rossellini

<!–[if IE 9]> <![endif]–>Isabella Rossellini talking to Ross in Friends

Unlike many other cameos in Friends Isabella Rossellini appeared as herself on the show. When Ross tried to flirt with her in front of his friends, she didn’t buy into his chat, and it didn’t quite go to plan for him.

The hilarity ensued with Rossellini’s classy and calm approach to Ross’ bumbling attempt to seduce her. The pair were worlds apart, and it was plain to see from the outset that she wouldn’t fall for him. Rossellini didn’t have a lot of screen time, but she was skilled enough to have a memorable impact on the episode.

7 Bruce Willis

<!–[if IE 9]> <![endif]–>Bruce Willis guest stars on Friends

Die Hard, Pulp Fiction, and The Sixth Sense are just a few of the big movies that Bruce Willis is known for. Playing Paul in Friends further exemplified Willis’ talent as a performer, taking on a completely different role from what he’d done before. Starting out as a daunting character who dated Rachel, he scared Ross who was seeing his daughter.

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Nevertheless, it soon became abundantly clear that Paul wasn’t as scary as he seemed. He had his own hang-ups and peculiar ways of hyping himself up. Fans know that Willis had an aptitude for playing hard characters. But seeing that he was happy to not take himself seriously and play a funny character only added to his well-rounded skill set.

6 Jeff Goldblum

<!–[if IE 9]> <![endif]–>Jeff Goldblum guest starring in Friends

Jeff Goldblum’s eccentricity has put him as an actor who regularly works with Wes Anderson, but this time, his unique characterization gave him his role on Friends. Joey auditions for a role in Leonard Hayes’ (Goldblum) project, who is a well-known director.

Joey is overawed by Leonard’s company, and Goldblum was the ideal actor to present the fictional director’s intimidating, but friendly personality. Leonard misinterpreted Joey’s need to use the bathroom as a character trait, which he liked. As Joey was so impressed with Leonard, he didn’t correct him, making the scene (and Goldblum’s appearance) one of the funniest in the show.

5 Gary Oldman

<!–[if IE 9]> <![endif]–>Gary Oldman in military uniform guest starring on Friends

As an actor playing an actor, Gary Oldman made his appearance when Joey was on set for a wartime movie. Joey stars opposite Richard Crosby (Oldman) who spits too much when he’s delivering his lines. Eventually, Joey sees the benefit of the actor’s peculiar technique and joins him.

The comedy really comes into play when Joey has to be on set on the day of Monica and Chandler’s wedding, and he wants to wrap up his scenes with Richard as quickly as possible. Unfortunately, Richard gets drunk and slows the production down. Oldman did a great job of portraying the two sides of Richard.

4 Susan Sarandon

<!–[if IE 9]> <![endif]–>Susan Sarandon guest stars on Friends

Joey’s career once again allowed for the inclusion of a celebrity appearance, this time from Susan Sarandon. Playing Cecilia Monroe as Jessica Lockhart in Days Of Our Lives, she found out through Joey that his character would have a brain transplant and become Jessica, removing Cecilia from the show.

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Cecilia didn’t take kindly to the news, but eventually warmed to Joey, helping him with his role before they ended up sleeping together. Sarandon brilliantly dramatized the news of her character losing her job, but was equally successful at transitioning to a warmer personality, all while maintaining a high level of humor.

3 Jennifer Coolidge

<!–[if IE 9]> <![endif]–>Phoebe and Monica feeling Amanda's abs in Friends

Friends was often able to make episodes relatable, none more so than “The One With Ross’ Tan,” which included Jennifer Coolidge as Amanda Buffamonteezi. An ex-friend of Monica and Phoebe, she was a self-centered character that had no real interest in other people.

Monica and Phoebe both wanted to avoid her, much to no avail. Coolidge conveyed the over-the-top, larger-than-life role, making it clear why her old buddies didn’t want to spend much time in her company. Though annoying for them both, it was hilarious for viewers.

2 Robin Williams & Billy Crystal

<!–[if IE 9]> <![endif]–>Billy Crystal and Robin Williams guest starring in Friends

Robin Williams and Billy Crystal came as a comedy duo in “The One With The Ultimate Fighting Champion,” with an equally hilarious presence from both. Cameo roles such as theirs contributed to making Friends one of the best comedy series of the 2000s, even though they had a short amount of screen time.

The two took a seat next to the six main characters in the coffee house when Tomas (Williams) told his friend Tim (Crystal) that his wife was sleeping with someone else. As it transpired, Tim was the adulterer, sending Tomas into a frenzy. The scene was succinct but gave Williams and Crystal enough time to get viewers laughing aloud, just as they always knew how.

1 Danny DeVito

<!–[if IE 9]> <![endif]–>Danny DeVito as a stripper in Friends

A minor role that was the focus of the episode’s title “The One Where The Stripper Cries” really enhanced the continual humor that Friends is famous for. Danny DeVito stepped into stripper Roy’s shoes, showing up for Phoebe’s bachelorette party. Monica and Rachel hadn’t realized she would want a stripper, so at the last minute, they hired Roy.

Roy’s stature wasn’t what Phoebe expected to see, but once he’d regained his breath after climbing up the stairs, he soon got into the swing of putting on a good show. DeVito is a dab hand at getting audiences laughing, and this episode expressed his talents again through his superb timing and physical comedy.

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