The 8 Best Friends Guest Stars, Ranked

Friends may be renowned for its cast, but the series also had some of the best guest star appearances in sitcom TV history.

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Can you imagine how different modern sitcoms would be if Friends had never seen the light of day? The show that defined the term “The One With…” has endured over three decades since its initial release, significantly affecting the course of TV culture in its wake.

The exploits of Ross, Rachel, Monica, Chandler, Phoebe, and Joey entertained audiences for ten seasons, with each cast member growing in reputation—and they were able to work with some of Hollywood’s finest actors and celebrities throughout the run of Friends.

We fondly remember the best guest stars to show up on Friends, who ranged from cult heroes to Hollywood icons of the age. But which of those guest star appearances were the best?

8. Hugh Laurie

As a desperate Rachel makes her way to London to stop Ross’ wedding to Emily, she sits next to a tall English gentleman on her flight who becomes quite irritated by Rachel and her nervousness.

To get away from her, he puts on his headphones—yet overhears Rachel telling another passenger her story with Ross, at which point Hugh Laurie’s character takes off his headphones and tells Rachel the blunt truth from an outsider’s perspective.

Laurie gives it to her in a straightforward-yet-sarcastic manner in his cameo role, which ends with him telling Rachel that she and Ross “were definitely on a break.”

7. Robin Williams & Billy Crystal

Few comedians have elicited stronger public adoration than Robin Williams. So, when he and his old friend Billy Crystal appeared in Central Perk, interrupting the gang when they ask to sit on the end of their favorite sofa, the moments that followed were special.

Williams and Crystal portray two men, with Williams’ character suspecting that his wife is cheating on him with her gynecologist—only for Crystal to reveal his suspicions are correct, because he’s the man responsible.

Williams explodes in a fit of anger and tears, sprinkling the sequence with his unique brand of hilarity.

6. Bruce Willis

When Ross begins dating one of his students, Rachel begins dating that student’s father: Paul Stevens, who’s played by the iconic Bruce Willis. His appearance lasts for a few episodes, and his persona is much like any clichéd Willis character with his gritty and intimidating presence.

He dislikes Ross for dating his daughter. But when Ross accidentally catches him posing strangely in the mirror, the pair suddenly begin to get along. Meanwhile, Rachel becomes disillusioned when Paul opens up his feelings to her and won’t stop crying, so she eventually dumps him.

It’s fun to witness the action hero lose his tough exterior and cry like a little child, as the series makes fun of Willis’ cinematic image.

5. Hank Azaria

Hank Azaria, the legendary Simpsons voice actor and on-screen performer, makes several appearances throughout the series as Phoebe’s one-time boyfriend David.

Unfortunately for Phoebe, David has to move to Minsk for his job, which forcibly ends their relationship despite them loving one another. However, he comes back to New York at a later time, only to find that Phoebe is dating Mike—and moves to propose to her anyway.

Azaria’s role in the show became intriguing as he presented a hard choice for Phoebe. Though, in the end, she chose correctly.

4. Isabella Rossellini

When Ross and Rachel each devise a list of celebrities they’re allowed to sleep with outside of their relationship, Ross puts Isabella Rossellini on his list—but then removes her for the “more local” Winona Ryder. 

One innocuous day at Central Perk, Isabella Rossellini walks in to grab a coffee. Ross is encouraged to speak to her and attempts to tell her about his list; however, she isn’t impressed and wittily removes herself from the conversation, leaving Ross embarrassed. 

Rossellini’s appearance in the series only lasted three minutes, but the impact has become one of Friends’ funniest cameo moments. 

3. Brad Pitt

Turning up as one of Ross’ old school friends, Brad Pitt—who was then-husband to Jennifer Aniston—appears in one of the series’ most memorable roles in one of the most memorable Thanksgiving episodes.

He plays Will Colbert, who has a strong dislike of Rachel because she bullied him during their school years. However, she has no idea who he is and thinks he’s attractive. He later reveals that he and Ross founded the “I Hate Rachel Club” at school, and Rachel becomes angry at him.

The episode ends well, but the excitement of seeing Pitt as a character that openly hates Aniston’s Rachel is a feeling that doesn’t grow cumbersome throughout—in fact, it’s quite a lot of fun!

2. Kathleen Turner

Meeting Chandler’s father became a big deal for Monica in the lead up to their wedding, while Chandler tried—in vain—to avoid it at all costs. However, Monica convinces Chandler to go with her to Las Vegas and see his father, who works as a drag artist with his own show.

Played by the indomitable Kathleen Turner, she brought Charles Bing to life with comedic flair and visceral undertones as he reveals his disappointment in Chandler for not speaking to him for many years.

In the end, Chandler apologizes and they reconcile, with Charles agreeing to attend Chandler and Monica’s wedding.

1. Danny DeVito

Who doesn’t want to see a beloved movie legend turn up on TV as a male stripper? Well, Friends made it happen for us when it delivered this hilarious sequence with aplomb. 

At Phoebe’s bachelorette party, she expects Rachel and Monica to have booked her a stripper—which, of course, they haven’t. So, after a last-minute booking, Danny DeVito arrives wearing a cop outfit and doing his best to entertain the ladies. 

What makes the sequence so funny is DeVito’s commitment to the material. He gives it his all as Officer Goodbody, an emotionally fragile stripper. And when Phoebe displays dissatisfaction at him and his performance, he angrily cancels the performance and starts crying.

As a bonafide icon, DeVito didn’t have to accept the role, but his presence as the stripper became one of the best parts of the entire series.

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