Brad Pitt
How could we forget Pitt (then married to Jennifer Aniston), who played Will, a co-founder of the "The I Hate Rachel Green Club”?
George Clooney and Noah Wyle
The worlds of mid-‘90s NBC heavy hitters collided when ER stars Clooney and Wyle showed up—in scrubs!—as the cute doctors treating Rachel’s ankle.
Julia Roberts
Roberts played Chandler’s former classmate, Susie Moss (aka “Susie Underpants”), whom he humiliated in the fourth grade. Jean-Claude Van Damme also guest starred in the same episode.
Winona Ryder
Back when the Fendi Baguette reigned supreme as the leading It bag of the early aughts, Winona Ryder made her appearance on the show as Melissa Warburton, Rachel's old college friend she kissed after a wild, sangria-fueled night of partying. Melissa pretended not to remember that encounter—until a kiss from Rachel to prove it happened elicits a long-held love confession.
Christina Applegate
Applegate played Amy, one of Rachel’s materialistic sisters, who comes over to spend Thanksgiving with the gang.
Anna Faris
Faris guest starred as the pregnant mother whose twins Monica and Chandler end up adopting.
Reese Witherspoon
Rachel’s younger sister Jill (an even more baby-faced Witherspoon!) comes into town and goes on a date with Ross.
Brooke Shields
Joey went on a date with Erika Ford (Shields), a fan who believed he’s actually Dr. Drake Ramoray—and quickly revealed her stalker tendencies.
Susan Sarandon
Joey got a chance to rejoin Days of Our Lives when his comatose character receives the brain of castmate Jessica Lockhart (Sarandon), who he ends up sleeping with off-screen.
Aisha Tyler
Tyler played Charlie, a professor who starts off dating Joey before becoming the love interest of fellow paleontologist Ross.
Tom Selleck
The famous mustachioed Selleck played Monica’s on-again, off-again boyfriend, Dr. Richard Burke.
Dakota Fanning
The former child actress played Mackenzie, the 8-year-old who is moving out of the house Monica and Chandler are buying, offering consolation to a saddened Joey.
Kristin Davis
Rachel and Phoebe found the perfect girl for Joey in Erin (Davis), but he doesn’t return her affections.
Billy Crystal and Robin Williams
The legendary comics cozied up on the famous Central Perk couch and shared a “private” conversation that had the rest of the friends all ears.
Helen Hunt
In another guest cameo by a fellow NBC star, Mad About You’s Hunt played Jamie, a customer of Phoebe’s twin sister Ursula, the always-confused waitress at their usual haunt.
Jon Favreau
Favreau played a recurring role as Monica’s boyfriend Pete, a wealthy man with Ultimate Fighting Champion aspirations.
Charlie Sheen
Chicken pox ruined what otherwise would’ve been a romantic weekend for Phoebe and her old Navy flame, Ryan (Sheen).
