One of the most famous TV shows in history, Friends ran for 10 years from 1994 - to 2004. It won the Emmy for Best Comedy Series in 2002. The show’s premise was pretty basic as 6 friends are trying to figure out life post-college as their friends have become their family. But it’s the cast chemistry and the brilliant writing that kept it going for a decade. Starring Jennifer Aniston, Courteney Cox, Lisa Kudrow, Matt LeBlanc, Matthew Perry, and David Schwimmer, Friends is one of the most quoted shows ever. Because of its popularity, it attracted a lot of famous guest stars. This particular group of guest stars also happens to be Oscar winners. But the real question is, how did they do on Friends?
12. Helen Hunt as Jamie Buchman
There was a time when Thursday nights on NBC were considered “Must-See.” One of those shows on Thursdays was Mad About You starring Helen Hunt and Paul Reiser. Lisa Kudrow played forgetful waitress Ursula, on the show. When Friends began, they addressed this as Ursula being Phoebe’s estranged twin sister. On a night of NBC crossovers, Mad About You characters Jamie (Hunt) and Fran (Leila Kenzle) dropped by Central Perk. When they see Phoebe, they assume it’s Ursula. Jamie and Fran mistake Phoebe’s confusion for Ursula’s usual disorientation.
In 1998, Hunt won the Best Actress Oscar for As Good As It Gets.
11. Robin Williams as Tomas
In 1997, Robin Williams and Billy Crystal were doing a press tour for their new film, Father’s Day. In a random cold open, the two appear in Central Perk in a clearly improvised skit. Williams plays Tomas who is weeping to his best friend that he found out his wife was having an affair only to discover that it’s Crystal she’s having the affair with. The Friends can only sit back and listen in astonishment as the drama unfolds. The scene has nothing to do with the episode and was clearly just an outlet for two tenured comedians to pop up on NBC’s biggest hit show. And how can you complain about watching that?
In 1998, Robin Williams took home the Best Supporting Actor Oscar for his role in Good Will Hunting.
10. Charlton Heston as Himself
Joey finally gets a big break and will be appearing in a movie with one of his acting idols, Charlton Heston. But in true Joey fashion, after a 3-day fishing trip, he oversleeps and doesn’t shower before sprinting to the set. Stinking to high heaven, he discovers that Mr. Heston has a shower in his dressing room. When Heston (playing himself) discovers Mr. Tribbiani, he gives him a lesson in acting, confidence, and staying the hell out of his dressing room.
Heston won the Best Actor Oscar in 1960 for Ben-Hur.
9. George Clooney as the Cute Doctor
When Rachel injures her ankle, she and Monica find themselves in the emergency room being treated by none other than George Clooney. He is not playing his ER character, Doug Ross, in the episode, but he and his ER co-star, Noah Wyle guest star as, you guessed it, cute doctors. When the girls decide to invite the doctors over, they are forced to pretend they are each other in order to get away with insurance fraud. Clooney and Wyle are increasingly frightened by Monica and Rachel’s behavior as it seems this is not the first time they’ve gotten dates at the hospital that haven’t turned out all that well.
Clooney has won two Oscars. One for Best Supporting Actor in 2005 for Syriana and one for being a producer for Argo which won Best Picture in 2012.
8. Jim Rash as the Nervous Passenger
Rachel is moving to France and Ross is desperate to stop her. Unfortunately, he’s at the wrong airport. In an act of desperation, Phoebe calls Rachel and tells her there’s a problem with the phalange (not a real plane part or a real word) of the plane. Rachel scoffs, but an anxious nearby passenger (Jim Rash) overhears her and freaks out causing the plane to be emptied. It’s a small role, but a clear indicator of Rash’s comedic abilities that a few years later he would illustrate to the world on Community.
Jim Rash took home an Oscar in 2012 for Best Adapted Screenplay with Alexander Payne and Nat Faxon for The Descendants.
7. Susan Sarandon as Cecilia Monroe
In Friends-land, Cecilia Monroe (Susan Sarandon) as Jessica Lockhart on Days of Our Lives is as famous as Susan Lucci as Erica Kane on All My Children. She is a character that people have loved for decades and is known for her infamous face slaps. So when Joey finds out he is going to have a new role, with her brain in his body, he is all too excited. However, he accidentally breaks the news to her that she is being fired off the show. So naturally, they end up in bed together. Sarandon’s daughter, Eva Amurri, also guest stars on the same episode within the episode.
Sarandon won her Oscar before her Friends appearance.
In 1995, she won Best Actress for Dead Man Walking.
6. Sean Penn as Eric
At Monica’s Halloween party, Phoebe meets her dream guy, Eric. (Sean Penn). Unfortunately, he’s engaged to her twin sister, Ursula (also played by Kudrow). When Phoebe discovers that Ursula has created an entirely fake persona to trick Eric into marrying her, she has to reveal the truth. At last, she and Eric can be together. The problem is, Phoebe looks exactly like the girl that just broke his heart, which only leads to double trouble.
Penn has won two Oscars for Best Actor. One for 2003’s Mystic River and the other for 2008’s Milk.
5. Gary Oldman as Richard Crosby
Gary Oldman may be known as one of the greatest dramatic actors of our time, and so is his Friends’ character, Richard Crosby. However, Oldman got to show off some comedic chops when Mr. Crosby not only loves to spit in his co-star's face when he acts, he also has a bad habit of showing up drunk. With a director who refuses to cancel the shoot unless Mr. Crosby isn’t able to walk, Joey resorts to desperate measures as he is in a time crunch to get to Monica and Chandler’s wedding to officiate.
Oldman won the Best Actor Oscar for The Darkest Hour in 2018.
4. Fisher Stevens as Roger
In Season 1, Phoebe has a new boyfriend named Roger. (Fisher Stevens). At first, everyone loves the psychoanalyst, but as he starts to pick them apart one by one, they all begin to really hate that guy. Defensive at first, Phoebe soon realizes she too hates that guy just as much as her friends.
Stevens took home the Oscar for Best Documentary in 2008 for producing The Cove.
3. Julia Roberts as Susie Moss
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In a special episode that aired after the Super Bowl in 1996, Chandler runs into his old friend Susie Moss (Julia Roberts). Back when they were young, Chandler was not so kind to her and pantsed her in front of the entire school. This led to her nickname “Susie Underpants” for the rest of her years in school. As Susie keeps flirting, Chandler can’t believe his luck. It all comes to a head when Susie leaves Chandler with nothing but his underwear in a restaurant bathroom as Susie finally gets her revenge.
Roberts won Best Actress for Erin Brockovich in 2001.
2. Reese Witherspoon as Jill Green
Rachel always speaks of her younger sisters with disdain. The first time we meet one of them is when Jill (Reese Witherspoon) arrives at Rachel’s doorstep after a fight with their father. (We meet her other sister Amy, played by Christina Applegate in Season 9.) Jill is just as spoiled and selfish as Rachel described. Seeing how Rachel was the same way when she arrived at Monica’s, she decides to take Jill under her wing to try and teach her how to be an adult in the real world. But when Jill starts to come on to Ross, Rachel realizes that she may be a lost cause and the sisters may have to come to blows. Even if Rachel isn’t with Ross, she doesn’t want him to be with her sister.
Witherspoon won her Best Actress Oscar in 2006 for Walk the Line.
1. Brad Pitt as Will Colbert
When one of Monica’s only friends from HS, Will (Brad Pitt) is in town for Thanksgiving, she invites him over. He has changed a bit since everyone last saw him, but one thing that hasn’t changed is his hatred of Rachel Green. Rachel has zero recollection of him and is even more stunned to learn that he and Ross had formed an “I hate Rachel Green” club. Thanksgiving episodes of Friends are classics for a reason, and this is one of the best. It’s a little bittersweet to watch now as Aniston and Pitt have since divorced, but it’s hard to beat the Will Colbert hair flip as he’s mocking his HS nemesis, Rachel Green.
Pitt has two Oscars. His first came in 2014 for producing Best Picture Winner 12 Years a Slave. His second came in 2020 for Best Supporting Actor in Once Upon a Time in Hollywood.