Top 20 Celebrity Guest Stars on Friends

#20: Dakota Fanning as Mackenzie

The “Ripley” star was a little girl when she appeared on “Friends”. However, her character, Mackenzie, was hilariously more mature than Joey. He was accompanying Monica and Chandler to their prospective new home, sulking about them getting a new place. Meanwhile, Mackenzie, whose parents were selling their house to the couple, was upset about losing it. The two bond, and Mackenzie gives Joey a much-needed lesson in letting go. Dakota was adorable, funny, and had all the sass we got from her in “Uptown Girls”. We wish we could’ve seen more of her!

#19: Isabella Rossellini as Herself

Imagine making a celebrity hall pass list, taking one of your crushes off it, and then bumping into them at your local coffee shop. That’s exactly what happens when Ross swaps Isabella Rossellini for Winona Ryder on his list. The problem is, the man thinks he has a chance with the legendary actress. Rossellini is graceful as ever, though intimidating, and Ross makes a complete fool of himself. What’s worse, the “Blue Velvet” star finds out about his list and isn’t too happy about not being on it. She doesn’t just turn him down, but also leaves him with a sick burn.

#18: Brooke Shields as Erika Ford

“The Blue Lagoon” actress played one of Joey’s love interests in “Friends”. Her character, Erika Ford, was a ten, but she was a stalker, convinced Joey was his “Days of our Lives” character, Dr. Drake. Things get out of hand when Erika thinks Joey’s cheating on her, and his friends come to his rescue, painting him as a fake. Joey and Erika share a passionate kiss before parting ways. Needless to say, Shields brought the perfect amount of over-the-top drama and ditzy glamor to her brief role. We still wonder how Erika fared in life, believing TV shows were real.

#17: Jon Lovitz as Steve

A job interview with a would-be boss who’s far from sober is a nightmare. In “Friends”, Jon Lovitz plays Steve, a restaurant owner who’s invited for dinner at Monica’s. She’s vying for a chef position at his establishment and has a lavish spread ready to impress him. However, Steve’s taste buds aren’t exactly at their best. The man is as high as a kite and couldn’t care less for a gourmet meal. Monica is rightfully bummed, but at least Phoebe gets revenge on her behalf by giving the guy a terrible massage. Steve turns up once in season nine, too, as Rachel’s self-deprecating blind date. With his impeccable comedic timing, the “Saturday Night Live” star stole every scene he was in.

#16: Jennifer Coolidge as Amanda Buffamonteezi

It is always an absolute delight to watch this icon on our screens. Her “Friends” character, Amanda, was a self-obsessed blonde bombshell with a lousy British accent. She used to be roommates with Phoebe and Monica and meets up with them after a long time. Unfortunately, Amanda turns out to be a harbinger of chaos and tells Monica about how Phoebe almost stopped being friends with her. This causes a rift between the two ladies, but it ultimately brings them closer. Jennifer Coolidge’s signature sass, larger-than-life screen presence, and unbeatable comedic talent make her cameo unforgettable. Her British accent has a fandom of its own, too.

#15: George Clooney & Noah Wyle as Dr. Michael Mitchell & Dr. Jeffrey Rosen

A petty fight led to Monica and Rachel fumbling two of the most handsome men ever. The “ER” stars play doctors who go on a double date with Geller and Green after meeting them at a hospital. Rachel was getting her ankle checked, but had switched identities with Monica so she could use her insurance. Later, during the date, the girls are worked up about their name swap and can’t stop throwing shade at each other as each other. Meanwhile, the docs grow hilariously uncomfortable. George and Noah are perfect heartthrobs here. Clooney’s suave demeanor and Wyle’s sweetheart charms give us all the butterflies. It’s a pity the double date did not go well.

#14: Teri Garr as Phoebe Abbott

The “Tootsie” actress played a very important role in “Friends”. She was Phoebe’s birth mother, who hadn’t been a part of her life until her daughter tracked her down. Right from her first appearance, the resemblance was striking. The Phoebes didn’t just look alike, but their mannerisms and even their voices were similar. So, when Abbott revealed that she was actually Buffay’s mother and not just her parents’ friend, it made total sense. The mother-daughter duo’s relationship starts rocky, but they slowly mend things. Teri Garr is so fitting as Phoebe Abbott that it’s a testament to the show’s picture-perfect casting. She matches Lisa Kudrow’s energy and complements her style of comedy. No one but Garr could’ve made this role as unforgettable as it is.

#13: Freddie Prinze Jr. as Sandy

A handsome, kind, empathetic, entertaining nanny who knows what he’s doing and gets along with everyone – that’s a dream come true for any parent! Well, except for Ross, apparently. When Rachel hires Sandy, the aforementioned nanny, to care for Emma, Ross is miffed. He thinks he’s too sensitive and can’t wrap his head around the idea of a man being a child’s caregiver. The fact that he’s a dreamboat – hello, Freddie Prinze Jr. – favored by Rachel and even approved by Joey, potentially added to his dislike. Just as Ross is about to let Sandy go, the manny gets him to open up about his emotional wounds instead. At that point, he probably understood what the Sandy hype was all about.

#12: Reese Witherspoon as Jill Green

We can never have enough of this queen. Reese Witherspoon plays Rachel’s youngest sister, Jill, in “Friends”, and the role was tailor-made for her. She absolutely nails Jill’s spoiled, bratty princess vibe. From shopping with daddy’s money to going after Ross just because Rachel told her not to, this Green had quite a few red flags. That being said. Reese delivers such a fun performance that we’re too entertained to judge her character. Sure, she kissed Ross to prove she could ‘have’ him, but it also made him realize he wanted something with Rachel again. We’ll count that as a win.

#11: Billy Crystal & Robin Williams as Tim & Thomas

“Friends” did viewers a great service by putting these two legends together and letting them do their thing. Billy Crystal and Robin Williams make a very short joint cameo in the show, and it is said that their entire scene was improvised! Apparently, the “Fathers' Day” stars just happened to be near the “Friends” set one day when they were asked to join an episode, and they obliged. The resulting bit, where their characters, Tim and Thomas, have an unhinged personal conversation publicly, was riotous. Despite their limited screentime, Crystal and Williams brilliantly showcased their comedic genius. Their chemistry, the way they played off of each other, and of course, Robin’s accent, created one of the best scenes in “Friends” history.

#10: Ben Stiller as Tommy

Soon after Ross and Rachel break up - and break our hearts! - Rachel brings Tommy to Joey's play. On the surface, things seem well, but in reality, Tommy’s got a real and not so secret rage that only Ross can see – at first. Eventually though, Ross is proven right when Tommy loses his mind on some unsuspecting victims. Stiller is no stranger to comedy, and his ability to take his energy from zero to 100 and back down again with only Ross as a witness is just what we like to see. All we know is that no one can yell like Ben Stiller.

#9: Julia Roberts as Susie Moss

We knew “Friends” was a heavy hitter when only midway through its second season, it aired a two-parter episode that featured not just one, but six guest stars and scored 52.9 million viewers. While Jean-Claude Van Damme brings the laughs- to say nothing of Chris Isaak, Fred Willard, and Dan Castellaneta- the standout for us is Julia Roberts. She plays Susie Moss, a girl from Chandler’s past who ends up playing a part in his present. Roberts was dating “Friends” star Matthew Perry when this episode was filmed, and their chemistry was visibly electric.

#8: Kathleen Turner as Helena Handbasket

Chandler Bing is a complex fellow, and he comes from a broken home thanks in part to his dad’s affair with the pool boy. Well, that sounds like a character we’d love to meet, and the brilliant minds behind “Friends” nailed the casting. In the role of the senior Bing is the sultry-voiced Kathleen Turner, who picks up on her real-life status as a gay icon to play Chandler’s drag queen parent. We can certainly see where the younger Bing gets his wonderful singing voice. We're not sure which pun we like better: her stage name Helena Handbasket, or that her burlesque show is called Viva Las Gay-gas.

#7: Alec Baldwin as Parker

For “The One in Massapequa,” “Friends” brought in a native… Massapequan, Alec Baldwin to portray Parker, Phoebe’s annoyingly positive boyfriend. Parker is one of those people who can see the silver lining in a hailstorm, but one you might want to lightly… punch in the face. It was really Baldwin’s first chance since “SNL” to show off his comedic chops, and he proved he knew how to time a line perfectly here. His signature blend of sarcasm is traded in for a sincerity that only a kid on a sugar rush would have. He’s like Santa Claus on Prozac at Disneyland… getting laid. Now there's a mental picture!

#6: Susan Sarandon as Cecilia Monroe / Jessica Lockhart

Who’s good at slapping, throwing drinks in people’s faces, and owning a room? Susan Sarandon. In this episode, she portrays legendary “Days of Our Lives” actress Cecilia Monroe, whose character Jessica Lockhart is killed off in order to bring Joey’s Dr. Drake Ramoray out of his coma – thanks to a brain transplant. We totally get why Matt LeBlanc would be nervous about acting alongside a pro like Sarandon, but he definitely rises to the occasion in this supersized episode, in which Cecilia helps bring out his inner Jessica-inside-of-Drake’s body. And guess what: she nabbed an Emmy nomination for her efforts.

#5: Gary Oldman as Richard Crosby

If you’re gonna get spit on, it may as well be by someone famous. As questionable as Joey Tribbiani’s acting talents may be, he’s had some impressive co-stars, including greats like Charlton Heston. But perhaps Joey’s best work came next to Shakespearean ac-tor, Richard Crosby, as played by the chameleonic Gary Oldman, who teaches Tribbiani the mark of a good actor. Oldman and Matt LeBlanc’s work together here was much more successful than their previous efforts in “Lost in Space” – at least Oldman earned an Emmy nod for “Friends.” It may not be an Academy Award, but he earned one of those eventually, anyway!

#4: Christina Applegate as Amy Green

When we met Rachel’s youngest sister Jill back in season 6, we didn’t think there was room for any more personality in her family, but man, were we wrong. Amy – as played by Christina Applegate – is Rachel’s younger, intensely honest sister, and a true Erin Brockovich – at least according to her. Originally, the writers wanted to bring Reese Witherspoon back for another appearance, but when she was unavailable, they turned to longtime sitcom actress Applegate to fill out the Green family tree. The result gave us a character we love to hate, and gave Applegate a Primetime Emmy Award.

#3: Danny DeVito as Officer Roy Goodbody

Who ya gonna call when your best friend demands a stripper… fast? Danny DeVito, obviously. The second we hear that goofy baritone voice on the other side of that door, we are excited - for all the wrong reasons. Not only did DeVito and his expert comedy chops completely steal the spotlight from a well-established cast, he earned an Emmy nod in the process. Officer Goodbody has got the moves and wears his heart on his tear-away sleeve, so we couldn’t be happier that Phoebe demanded pee-pees flying about at her bachelorette party. “Tainted Love” will never sound the same.

#2: Bruce Willis as Paul Stevens

For how much the friends say they love Die Hard, it's all too hilarious to bring in John McClane himself. He’s still a macho man, but his performance is an absolute roller coaster of emotions -- from a neat guy to… Chicken Boy? How'd they pull that off? On the set of The Whole Nine Yards, Willis bet against co-star Matthew Perry that the film wouldn't do too well at the box office. When the film opened at #1, Willis made good with the bet and gave his “Friends” salary to charity. We guess he’ll just have to settle for the Emmy he got. Not half-bad, you love machine.

Before we unveil our top pick, here are a few honorable mentions.

Hugh Laurie as the Man on the Plane Beside Rachel

He Had the Best Reactions to Green’s Love Saga

Winona Ryder as Melissa Warburton

Her Long-Held Love for Rachel Made for an Entertaining Episode

Steve Zahn as Duncan

He Was Phoebe’s Gay Husband, but Comes Out as Straight

Sean Penn as Eric

He Romances Both the Buffay Twins!

Greg Kinnear as Benjamin Hobart

He Gave Us Some Big Laughs as Ross’s Rival in Love and Academics

#1: Brad Pitt as Will Colbert

When it comes to our top pick, we’ll just let the studio audience do the screaming for us. Brad Pitt’s character Will was Ross’ pal in high school, who helped co-found the “I-hate-Rachel” club and started a persistent rumor about his nemesis. Pitt was on the show to plug his flick “Spy Game,” but that was overshadowed pretty quickly by his onscreen chemistry with his wife at the time, Jennifer Aniston. His blind hatred of Rachel is definitely worthy of his Emmy nomination, but we do kinda wish we’d gotten to see him don a fat suit in a flashback… We’re with Phoebe on how good he looks though.

Which of these characters left the deepest impression on you? Tell us in the comments!