Friends took the simple concept of six close-knit friends navigating the ups and downs of their twenties and turned it into a pop culture phenomenon that continues to captivate audiences even two decades after its series finale. While Monica, Chandler, Joey, Phoebe, Ross, and Rachel have secured permanent spots in fans' hearts, Friends also gave us countless iconic and unforgettable side characters, from the official co-founder of the “I Hate Rachel” club to the hilariously sad stripper at Phoebe’s bachelorette party.
From awkward exes and A-list crushes to disgruntled friends and pushy neighbors, here are the 10 best celebrity guest cameos Friends pulled in during its 10-season run:
Reese Witherspoon
Friends has had its fair share of quirky relatives, from Phoebe’s half-brother Frank to Chandler’s estranged dad, but one who truly made her mark was Rachel’s favourite sister, Amy Green, played by Legally Blonde’s Reese Witherspoon. Amy visits in “The One with Rachel’s Sister” during Season 6 after being cut off by their father. Though she only appeared in two episodes, Amy left a lasting impression, not just for briefly dating Ross and adding a fun twist to the ongoing Ross-Rachel saga, but also for highlighting how much Rachel had grown since running away from her old life back in Season 1. Witherspoon and Aniston maintained their off-screen friendship long after Friends ended and later reunited as co-stars in Apple TV’s newsroom drama, The Morning Show.
Brad Pitt
Brad Pitt and Jennifer Aniston were Hollywood’s golden couple in the late '90s, long before the Brangelina era. Unlike Brangelina, who worked together on two feature films, Mr. & Mrs. Smith, which famously sparked their initial romance, and By the Sea, Pitt and Aniston only shared screen space once, when Pitt made a guest appearance in Season 8’s Thanksgiving episode, “The One With the Rumor.” In the episode, Pitt plays the role of Will, Ross’ longtime school friend and Rachel’s nemesis, who co-founded the “I Hate Rachel” club back in high school. Watching Hollywood’s sweethearts play frenemies on one of the biggest sitcoms of the '90s definitely marked a memorable moment in television history.
Ellen Pompeo
After 21 seasons, it’s hard to imagine Ellen Pompeo as anyone other than Meredith Grey on Grey's Anatomy. However, before becoming one of the most iconic doctors in television history, Pompeo made a guest appearance on Friends as Missy Goldberg in the episode “The One Where the Stripper Cries.” She plays the girl Ross and Chandler both had a crush on back in college, making for a hilariously awkward reunion years later.
Danny DeVito
Ellen Pompeo isn’t the only famous face in “The One Where the Stripper Cries.” The episode also stars Danny DeVito, who you may recognise from his memorable roles on the hit sitcoms Taxi and It’s Always Sunny in Philadelphia, but after his Emmy-winning performance as a taxi driver in Taxi, DeVito surprised fans by playing the role of a sad, ageing stripper at Phoebe’s bachelorette party, definitely one of the most lasting celebrity performances in the series’ 10-season run.
Jennifer Coolidge
The White Lotus revived Jennifer Coolidge’s career and gave her the well-earned recognition and boost she truly deserves. Often cast in supporting roles or typecast in a certain way, Coolidge hasn’t had it easy by any means, but no matter how big or small the part, she always manages to leave a lasting impression. You might recognise her from 2 Broke Girls, American Pie, and Legally Blonde, but she also played the role of Amanda Buffamonteezi, Monica and Phoebe’s longtime friend who causes friction within the group when she decides to move back to New York City in “The One With Ross’ Tan.” Interestingly enough, Coolidge later found a more prominent role in the Friends spin-off series Joey, as Joey Tribbiani’s eccentric new agent, Bobby.
George Clooney
George Clooney has had a long-standing relationship with NBC, given that his stint as Doug Ross on the network’s hit medical drama ER offered him a major head start in his acting career. Friends gave ER fans a moment to relive the glory days of the show once again by casting George Clooney and his co-star Noah Wyle as the charming doctors Monica and Rachel double-date in Season 1’s episode “The One with Two Parts.” This was still the early days of Friends, and NBC’s crossover cameo helped push the series further into the spotlight.
Ben Stiller
Ben Stiller and Jennifer Aniston have a long-standing friendship dating back to their time on Friends when he guest-starred as her boyfriend in “The One with the Screamer,” where the entire group is taken aback by his short temper. The duo went on to work together again after the series wrapped in the lovable rom-com Along Came Polly, where Stiller plays a newlywed who gets dumped on his honeymoon, only to give love a second chance after reconnecting with his wildly different former school friend, Polly.
Charlie Sheen
Charlie Sheen is best known for, well, playing Charlie Harper, a womanising jingle writer with deep commitment issues on Chuck Lorre’s standout sitcom Two and a Half Men. That is what makes his guest appearance on Friends as Phoebe’s long-lost love interest (also a musician), who’s deeply in love with her and has to resist the urge of physical contact due to chicken pox, hilarious and somewhat uncanny. He appears on the series in the episode “The One with the Chicken Pox” in Season 2, which predates his stint on Two and a Half Men. It left a formidable impression and gave a glimpse of his comedic potential in sitcoms.
Julia Roberts
One of the things we love most about Friends is how the writers cleverly wove the actors’ real-life romances into the characters’ storylines. Matthew Perry and Julia Roberts surprised everyone with their whirlwind romance in 1995, which made her appearance in Friends’ Super Bowl special episode, “The One After the Superbowl,” in Season 2, even more memorable. If you enjoyed Roberts’ feisty cameo in the series, you should also check her out in Runaway Bride and Pretty Woman.
Helen Hunt
Not a lot of people know this, but before Lisa Kudrow was cast as Phoebe Buffay on Friends, she was already playing the role of Ursula, an ineffective waitress at Riff’s in the series Mad About You. So when Friends took off, the show creators brought Mad About You’s You Helen Hunt and her co-star Leila Kenzle down to Central Perk as coffee shop customers who confuse Phoebe for her twin sister Ursula to close out the loop and pay a fun nod to the fans who understood the reference.
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