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10 Best Friends Guest Stars, Ranked

Friends

The 1990s sitcom Friends stands as one of the best TV comedic shows of all time, as well as one of the most–if not the most—rewatchable TV show ever. It's one of those shows you can rewatch countless times and laugh all the same. The hilarious interactions of the main cast and the ridiculous situations they get themselves into never cease to entertain.

RELATED: Friends Likely Leaving Netflix After Warner Streaming Service Launches

But aside from the six friends, the show has also had some pretty awesome guest stars over its 10-season run, who have been responsible for some of the shows funniest moments. In their honor, here are the 10 of the best Friends guest stars, ranked.

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Friends Winona Ryder
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10 WINONA RYDER

Friends Winona Ryder

Stranger Things star Winona Ryder made an appearance in the season seven Friends episode “The One with Rachel’s Big Kiss.” Ryder portrayed Melissa, Rachel’s friend from college, whom Rachel claims she shared a kiss with after having too much sangria. Phoebe, however, doesn’t buy the story because she thinks Rachel is “so vanilla.”

To prove that she’s not vanilla, Rachel invites Phoebe to have dinner with her and Melissa. Unfortunately for Rachel, Melissa denies that the kiss ever happened. Not one to give up easily, Rachel plants one on Melissa, who then declares her love for Rachel. Turns out Rachel is a good kisser, which Phoebe then puts to a test, deciding that she's had better. Funnily enough, in season three, Ross put Winona Ryder on his Freebie list and yet she wanted Rachel.

9 SUSAN SARANDON

Friends Susan Sarandon

In “The One with Joey’s New Brain,” Joey doesn't exactly get a new brain, but his character on Days of Our Lives does because soap operas. As it turned out, one of the biggest stars on the show is getting the ax and the producers want to put her character's brain into the head of Joey’s comatose character, Drake Ramoray. Susan Sarandon plays Cecilia Monroe who portrays the fictional Days of Our Lives character Jessica Lockhart, who's about to get thrown from a horse into an electric fence.

Cecilia decides to help Joey better understand how Jessica’s mind works so that he could do a faithful impression of Drake with Jessica's brain — or is an impression of Jessica with Drake's face? Of course, this is Joey we’re talking about and naturally, he ends up sleeping with her, and Rachel and Monica get to fangirl over her the morning after.

8 REESE WITHERSPOON

Friends Reese Witherspoon

The Green sisters truly are something else. We thought there couldn’t possibly be a person out there who’s more spoiled, self-centered, and disconnected from the real world than Rachel. Oh boy, how wrong we were. Enter, Reese Witherspoon as Jill Green, Rachel’s youngest sister who makes season one Rachel look like a well-adjusted adult by comparison.

RELATED: Legally Blonde 3 Moving Forward, Reese Witherspoon In Talks to Return

So, what did Jill do? Well, she bought a boat for a friend—you know, as you do—and then her father threatened to cut her off. She ran to Rachel, who decided to help her start a life on her own, but Jill proved not to have Rachel’s resolve. She went on a shopping spree and tried to seduce Ross to spite Rachel, ultimately running back to daddy.

7 JASON ALEXANDER

Friends Jason Alexander

In “The One Where Rosita Dies,” Phoebe’s job at a call center turns into a suicide prevention lifeline when she encounters a potential client who tells her that he’s planning to take his own life. The man in question, Earl, was portrayed by none other than the Seinfeld star Jason Alexander (aka George Costanza). Earl hangs up, but Phoebe is determined to help him and ends up going to his office.

RELATED: 15 Minor Seinfeld Characters Who Stole The Show Every Time

In the true spirit of Phoebe Buffay, she makes up a few details about her mother and her suicide and gets Earl to give up on the idea.

There is actually a fan theory out there that Earl is, in fact, Seinfeld's George Costanza in disguise because of how similar the two are.

6 HUGH LAURIE

Friends Hugh Laurie

Before he was Dr. House, Hugh Laurie had a small, but hilarious, role in the season four episode “The One with Ross’ Wedding: Part Two.” Credited as the Gentleman on the Plane, Laurie sat next to Rachel on her flight to London to stop Ross from marrying Emily. Rachel ended up telling the entire story to the guy across from her, but Laurie heard her even over his headphones and decided to interject.

He let Rachel know, in no uncertain terms, that what she was about to do won’t do anyone any good. He called her out for being a horrible person and even went as far as informing Rachel that they were on a break, all the while sounding like a British Dr. House.

5 CHRISTINA APPLEGATE

Friends Christina Applegate

In season nine, we meet Rachel’s sister Amy in “The One with Rachel’s Other Sister.” Portrayed by the hilarious Christina Applegate, Amy shows up at Rachel’s door on Thanksgiving Day totally out of the blue. Spoiled, pampered, and self-absorbed even more so than the season one Rachel, Amy immediately gets off on the wrong foot with everyone.

She thinks Rachel and Ross had a son Emmett, and even when she’s told that it’s a girl, named Emma, Amy keeps calling the baby Emily. She doesn’t remember Ross but does remember Rachel’s fat friend’s creepy brother with an ugly afro. Applegate returned in season 10 to babysit little Emma, at which point she mistook Ross for the falafel guy from around the corner.

4 GEORGE CLOONEY AND NOAH WYLE

Friends George Clooney Noah Wyle

In “The One with Two Parts: Part 2,” we got one of the show's coolest cameos when George Clooney and Noah Wyle, at the time stars of NBC’s hit medical drama ER, guest-starred on Friends as two handsome ER doctors.

RELATED: Friends: The 15 All-Time Best (And 10 Worst) Episodes, Officially Ranked

They end up going on a double date with Monica and Rachel – only, they think that Monica is Rachel and Rachel is Monica... Because Rachel has no medical insurance, the girls are committing insurance fraud to avoid expensive medical bills. The poor doctors are already worried that Monica and Rachel would turn out to be the same as other women they’ve met on the job, i.e. crazy, and are in for quite the spectacle when their dates start revealing embarrassing details about each other while staying “in character.”

3 BRUCE WILLIS

Friends Bruce Willis

Remember that time when Ross dated a student? And then Rachel started dating Ross’s student's/girlfriend’s dad? Yea, those were some pretty hilarious times. We can only imagine what went through Ross’s head when he realized that his young girlfriend’s father is freaking John McClain. Well, sort of anyway.

RELATED: Friends: The 15 All-Time Best (And 10 Worst) Episodes, Officially Ranked

Bruce Willis appeared on a number of Friends episodes as Elizabeth's dad, Paul, and has had some pretty fantastic moments; every single time he interacted with Ross, his relationship with Rachel, especially when he opened up and started crying uncontrollably. To top it all off, the most awkward double date ever happened where Paul learned about Ross’s failed marriages. But, most of all, Paul was just a really neat guy.

2 JULIA ROBERTS

Friends Julia Roberts

A man walks into the restaurant restroom fully clothed and walks out several minutes later carrying a door to cover his half-naked body. This hilarious scene comes from the season two episode “The One After the Superbowl: Part 2” and the man in question is Chandler Bing. But how did he end up in such a predicament?

Well, it all goes back to the fourth grade when he lifted up the skirt of one Susie Moss, later nicknamed Susie Underpants, portrayed by the amazing Julia Roberts. After reuniting with the man who ruined her life, Susie decided to get revenge by deserting him in a public restroom, clad in nothing but a pink thong. Susie's rant before she runs out on Chandler is hilarious.

1 BRAD PITT

Friends Brad Pitt

In season eight episode “The One with the Rumor,” Brad Pitt guest stars as Will, Ross’s previously overweight high school friend/co-founder of the “I hate Rachel Green Club.” Monica invites Will to her Thanksgiving dinner, but the party goes south when it turns out that, despite looking... well like Brad Pitt, Will still holds a grudge over how Rachel treated him back in high school.

NEXT: 4 Cameos That Hurt Friends (And 21 That Saved It)

Hilarity ensues as age-old secrets and rumors are revealed left and right. Brad Pitt gets to tease his then-wife about her “teenie weenie,” and say lines like “My two greatest enemies Ross, Rachel Green, and complex carbohydrates” while giving Rachel his most vicious death stare.

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