The Best Celeb Guest Appearances on Friends

Before How I Met Your Mother, New Girl and a dozen other bestie-based shows, Friends made chit-chatting over coffee and hanging couch side cool. Ten seasons later, the classic comedy was still causing laughing fits on a weekly basis. A who’s who of famous faces, the television show was known for its witty one-liners, close-knit gang and revolving door of big names. From up-and-comers to superstars, the fan favourite welcomed a long list of somebodies throughout its remarkable run. Even better than laughing out loud and relating to the old school squad, re-watching Friends to throw it back to the ‘90s. A time when George Clooney claimed bachelor status for life and Charlie Sheen was (actually) winning. With so many celeb guest appearances to choose from, it’s hard to pick the best. It’s definitely worth the second binge-fest to see if your can’t miss moments match.

1. Brad Pitt (Season 8: The One with the Rumour)

The year: 2001 For those who are always and forever Team Jen, this episode is definitely must-see TV. Putting his comedy skills to work, Pitt plays Will Colbert, a high school classmate of Rachel, Ross and Monica from way back. Although married in real life, the couple takes on-screen frenemy status to the next level. Will reveals that in high school, he was a member of the I Hate Rachel Green Club. Rude!

2. Julia Roberts + Jean-Claude Van Damme (Season 2: The One After the Super Bowl)

Same episode alert! In this star-studded episode, Roberts plays Susie (“Susie Underpants”), Chandler’s classmate from the fourth grade. Looking to seek revenge more than score a date, she causes one of the most memorable scenes from the series. After stealing all of his clothes and leaving him in a public washroom, Chandler is seen exiting a fancy restaurant wearing only a hot pink thong and carrying a bathroom stall door to protect his private parts. That’s one way to get even. As for Jean-Claude, he plays himself in the ep. Just like Rach and Mon, we think he’s easy on the eyes.

3. Freddie Prinze Jr. (Season 9: The One with the Male Nanny)

As the prince of ‘90s rom-coms, Freddie Prinze Jr. personifies nostalgia. Switching things up, he appears as Sandy, the sensitive male nanny that R+R hire to care for Emma. As a forward thinking episode, the 30-minute block explores role reversal, stereotypes and gender issues. Plus, long before the trend, the character made gender-neutral names a thing. Three tears for Sandy!

4. George Clooney + Noah Wyle (Season 1: The One with Two Parts: Part 2)

Kind of a two for one doctor deal, George Clooney and Noah Wyle channeled ER vibes while guest starring as a pair of stethoscope wearing, smooth operating docs. With Rachel and Monica in the middle of an identity swap, their double date doesn’t exactly go as planned. With a change in name, all bets are off and all secrets are out.

5. Adam Goldberg (Season 2)

Although we weren’t happy about Joey and Chandler briefly falling out, Goldberg’s stint as Eddie Menuek (“Crazy Eddie”) made up for it. As Chandler’s new roomie, he’s a little kooky and a lot crazy. Similar to his goldfish, Buddy, his over the top, freak of nature antics are on point.

6. Reese Witherspoon + Christina Applegate (Season 6: The One with Rachel’s Sister + Season 9:

The One with Rachel’s Other Sister; The One Where Chandler Can’t Cry) While the blonde beauties appear separately as a member of the Green clan, both show up unannounced and share similar personal traits. Taking on the roles of Jill and Amy, respectively, the related combo of ditzy and spoiled makes for light and funny entertainment. With each sister having a different approach to interacting with Ross: asking him on a date vs. forgetting who he is, both times the sibling reunion is short and sweet.

7. Charlie Sheen (Season 2: The One with the Chicken Pox)

In this itch-central episode, Sheen plays Phoebe’s long-lost lover. As a military man, who knocks on the door holding a bouquet and sporting a uniform, the bad boy has never looked better. As the two fight the good fight together, scratching becomes a new form of foreplay.

8. Steve Zahn (Season 2: The One with Phoebe’s Husband)

Keeping with Phoebe’s quirky personality and colourful relationship history, Zahn is introduced to the gang as a gay Canadian ice dancer, who she once married to help him gain U.S. citizenship. Because, you know, she’s like that. Turns out he’s not gay and needs a divorce in order to pop the question for a second time – don’t worry, not to Phoebe (or Ursula).