The 16 Best Friends Guest Stars, Ranked

For 10 seasons, "Friends" was a tour de force comedy about friendship, dating, and life in the big city. During that time, many actors — quite a few of them famous — guest starred on the show. All of these guest stars brought something unique and engaging, and many times, they treated us to depictions of characters we wouldn't have seen anywhere else. Plus, many of these characters had unique senses of humor, from Will (Brad Pitt) and his "I Hate Rachel Green" club to Parker (Alec Baldwin) and his amazing optimism. As a result, the caliber of guest talent on the series was top-notch.

While we can't cover all of the guest stars "Friends" ever had (and there are many, many good ones), we are covering 16 of the very best. The rank and stars shown here were picked by this piece's writer — a resident "Friends" fan — although rankings from other outlets were also consulted to arrive at the order you see here. No recurring roles were considered, so no Janice (Maggie Wheeler) or Geller parents; only stars who were in three episodes or less were included in this list. Here are the 16 best "Friends" guest stars, ranked.

When Jennifer Coolidge guest starred in "Friends" Season 10, Episode 3 in 2003, she wasn't as well known as she is now, which meant she was largely overlooked in this role. However, she was perfect as Amanda Buffamonteezi, a woman who can't help bragging about everything happening in her life. Coolidge managed to make the role her own, fake British accent and all. She made Amanda completely hateable and yet hilarious, especially when she's bragging about her natural scent or dancing for Chandler (Matthew Perry).

Amanda even manages to accidentally reveal that Phoebe (Lisa Kudrow) once tried to cut Monica (Courteney Cox) out as a friend — the exact thing that Monica and Phoebe are trying to do to her. As Amanda says, she feels "like a perfect arse" for letting the beans slip. In the end, Chandler sums it up well: "That fake British woman's a real b****, but she sure can dance." Of course, if you're not impressed with her dancing either, we'll forgive you. 

While Coolidge was great in the role of Amanda, she's in last place on this list due to the character's sheer annoying personality. Although it's done on purpose (and done very well), many viewers were likely put off by the brash, show-offy character — much like Monica and Phoebe. 

In 1995, Steve Zahn guest starred as the titular husband, Duncan, in Season 2's "The One with Phoebe's Husband," but with the caveat that his character is gay and Phoebe just married him so he could get a green card. Having someone openly gay on TV was very cutting-edge at the time, and everyone in the cast lived up to the challenge. The other characters believe that Duncan didn't do anything wrong, but Phoebe made a mistake by marrying him because she has real feelings for him.

By the time Phoebe sees Duncan on "Friends," it has been several years since he'd been gone, yet she still holds a flame for him. So Phoebe is devastated to learn that he is, in fact, straight, and met a girl he wants to marry. Unfortunately, the dynamic doesn't quite stand the test of time — it's a lot less shocking today than it was when it aired — but Zahn does a fantastic job with the tricky nature of the role, making Duncan smart and funny. By flipping gay tropes on their head, the show makes a great point about people not choosing their sexuality. 

Before Alec Baldwin made his mark on "30 Rock" in 2006, he guest starred on "Friends" for two episodes in 2002. This was Season 8 and, even though Monica and Chandler are married, Ross (David Schwimmer) and Rachel (Jennifer Aniston) are having a baby, and Joey (Matt LeBlanc) is ... doing whatever he does, Phoebe is still looking for Mr. Right. Thankfully, she thinks for a moment she has found him in Baldwin's Parker in Episodes 17 and 18. Despite the rest of the friends' reactions, she likes his positivity — or so she says.

But then she realizes even she doesn't have the mental fortitude to stand up to his affirmations about everything. She tries to get on board the Parker train, but by the time the two of them are back at her apartment, she's had it, telling him he's "like Santa Claus on Prozac at Disneyland getting laid." Phoebe dumps him, after which Parker knocks on her door to tell her they've just had the best fight ever.

Baldwin more than held his own playing an optimist so cloying even Phoebe couldn't stand it. In fact, he was so annoying that even some of the viewers watching might have turned it off, but he gets this ranking because of his large role in the show.

Freddie Prinze Jr. was at the height of his popularity, having done a string of popular movies including "Scooby Doo" earlier in the year, when he did a guest spot on "Friends" in 2002. In Episode 6 of Season 9, titled "The One with the Male Nanny," he plays a nanny named Sandy whom Ross has trouble with simply because he's a guy. Sandy is completely secure with himself but Ross questions him at every turn, concluding he has to "be at least bi" to be a male nanny.

When Ross finally convinces Rachel to let him fire Sandy, she makes sure he knows it's because of Ross, not her. But it isn't a total loss. Sandy has a fan in Joey whom he periodically gives lessons to about friendship and other easy-to-understand topics. According to Joey, it's "the cheapest college ever."

Prinze Jr. completely committed to the part, getting choked up at the slightest thing and imparting words of wisdom to Emma ... and Joey. Even though the part is outdated today, he made Sandy funny and surprisingly understanding in even the worst of circumstances.

Winona Ryder guest starred as one of Rachel's former sorority sisters, Melissa Warburton, on Episode 20, Season 7 of "Friends." In the episode, she is as entitled and airheaded as many of the people in Rachel's life, but with a twist: Rachel and Melissa kissed in college — or at least that's what Rachel says. But when Phoebe doesn't believe her, she has Phoebe come to dinner with her and Melissa so she can bring up the incident ... and Melissa tells them it didn't happen.

Melissa and Phoebe are on the same page, and Rachel is so annoyed that Melissa doesn't remember that, to try to jog her memory, Rachel kisses her. Of course, Melissa takes this as a gesture of love and goes all gooey for Rachel. Misunderstanding aside, though, at least Rachel gets her confirmation. Their dynamic is a little dated — after all, today, many people wouldn't deny kissing someone of the same sex — but Ryder is hilarious as a former hookup of Rachel's who turns out to have completely unexpected feelings for her former schoolmate.

Sean Penn has a very serious reputation; he does serious movies and supports serious causes. But it turns out he has a funny side too, and one way he showed it was through a guest starring role on "Friends." He plays Eric in two episodes of Season 8 and is amusing, although not laugh-out-loud hilarious, in the role, which requires him to be Phoebe's identical twin sister Ursula's fiance.

Eric starts the first episode deeply in love with Ursula only to discover from Phoebe that she'd lied about basically everything about herself. But sparks fly between Eric and Phoebe and, in the second episode Penn appeared in, Eric asks Phoebe out. The problem is that Phoebe looks just like Ursula. Phoebe manages to get Eric to temporarily forget about the problem by kissing him, but when he accidentally has sex with Ursula instead of her while she's out, she dumps him. Penn managed to bring a light touch to the role that worked for the character and matched Phoebe's energy well.

Reese Witherspoon guest starred as Jill Green in two episodes of Season 6, the first of Rachel's two sisters to appear on "Friends," and she did not disappoint. She comes to Rachel after her father cuts her off and tells her to learn about being thrifty from "the one daughter he's actually proud of." While Rachel takes on Jill as a project, things quickly get derailed when Jill sparks up a relationship with Ross. Sure, Jill initially wasn't interested in him, but after Rachel accidentally encourages her, Jill asks Ross out.

Soon though, Ross is closing his drapes and Rachel is wondering what that means. At coffee the next day, she learns nothing happened, but Jill and Ross have a date for that night, Valentine's Day. When Rachel freaks out, Ross agrees to call the date off. But Jill, who has become increasingly annoying, is surprised by Rachel's desire not to have her date Ross, and retaliates by worming her way into Ross's apartment and then making out with him.

Witherspoon's Jill does a great job getting in the middle of Ross and Rachel's will-they/won't-they dynamic and then taking it personally when both of them choose each other over her. She isn't nearly as entertaining as Rachel's other sister Amy, but she is funny enough to make it to No. 10 on this list.

Jon Lovitz isn't the biggest name on this list but he had a genuinely funny guest-starring role all the way back in the Season 1 episode "The One with the Stoned Guy." He was the stoned guy, Steve, a restaurateur friend of Phoebe's in need of a chef for his kitchen. Monica wants the job and has him over to her apartment for a trial run, but in the car on the way over, Steve sparks up a joint and the rest of the night ends up being a blur for him. This leads to some hilarious food-related jokes, like Steve saying "tartlets" several times before announcing that the "word has lost all meaning."

Lovitz wasn't quite as funny when he guested in Episode 14 of Season 9. Although Rachel is there when Steve has his horrendous night with Monica, neither of them appears to remember one another when Phoebe sets them up for a blind date eight years later. By this point, Steve still loves pot, but instead of making him funny, it makes him sad. Lovitz's first guest-starring role was so funny it lands him on this list, but his second is what makes him rank so low.

When Ben Stiller guest starred on "Friends" he was still a year away from the start of the height of his career with "There's Something About Mary," but his turn here showed how he could make being a complete jerk absolutely hysterical. Stiller guest stars as Rachel's date Tommy in Episode 22 of Season 3, and while Tommy seems nice enough at first, Ross realizes he's not when Tommy yells at a couple that has sat in their seats at the theater. Ross spends the rest of the night waiting for Tommy to crack, but since no one but Ross saw Tommy yell at anyone, no one believes him.

That all changes when Tommy encounters the duck and the chick in Joey and Chandler's apartment when he goes to use the phone there. The chick poops in his hand and then the duck annoys him by quacking, and to top it all off, the "Friends" gang sees the whole thing from the door of the apartment. Obviously, that's the end of Tommy dating Rachel, but Stiller did a fantastic job with a role that required him to be a good guy and then a terror at the drop of a hat. His angry musings were a combination of mean and so over-the-top it's funny, making his place right in the middle of the list appropriate.

In Season 6, Ross starts dating one of his students, Elizabeth (Alexandra Holden) — but the storyline reaches another level when her father, Paul Stevens, comes to visit in a three-episode arc starting with Episode 21. Paul is played by Bruce Willis and he does not like Ross, but he turns out to like Rachel a whole lot. In fact, Rachel and Paul get very cozy, and Rachel tries to talk Ross up. However, after hearing Ross mock his age, Paul tells Ross if he doesn't break up with Elizabeth, he'll call the university and have him fired.

Ross and Elizabeth end up hiding their relationship from Paul, but when both couples go up to the Stevens' country house for the weekend, it appears Ross and Elizabeth are going to get caught — until Ross sees something Paul would prefer him not to. Suddenly, Paul is showing him to the guest room and not the exit.

Willis' stint on the show had to come to an end sometime — after all, a busy actor only has so much time — and Paul ends up getting a little too in touch with his feelings, then is dumped by Rachel. Despite the aspects of the character that were less than tough, Willis managed to knock the role out of the park, playing several different colors of Paul across three episodes and scoring with the audience every time.

Susan Sarandon guest starred in "Friends" Season 7, Episode 15, "The One with Joey's New Brain" as a soap opera star; not a far stretch from her real-life movie star profession. However, Sarandon's Cecilia Monroe really lived her character Jessica's more extreme moments, berating everyone and slapping them at will. So when Joey finds out his character is getting Jessica's brain on "Days of Our Lives," and that means Cecilia is leaving the show, Cecilia gives him hell. But it turns out Joey is right, so Cecilia agrees to teach him how to be Jessica.

Sarandon is hilarious as a spoiled, scorned star, telling Joey how to own the room, bragging about how different Mexican cinema would have been today if she had left "Days of Our Lives" 15 years prior, and kissing him with both her hands on his face because then "the camera only sees her." Sarandon and Matt LeBlanc's chemistry was so good that she earns the sixth spot on the list.

Danny DeVito guest starred in Season 10 in an episode called "The One Where the Stripper Cries," and as the titular stripper he does indeed cry — because Phoebe is mean. DeVito plays Officer Goodbody, the somewhat inappropriately named stripper who comes to Phoebe's bachelorette party at the last minute. He tries to introduce her to "the long arm of the law," but Phoebe cringes the whole time because Officer Goodbody is obviously past his prime. When he catches on, the waterworks start. 

Phoebe ends up feeling bad for him and encourages him to finish his last dance. He proceeds to writhe all around Monica's apartment but doesn't get very far, as he taps out after tearing off both of his sleeves. While it's an ignoble end for the stripper, for DeVito it was a triumph. He was hilarious and had all the right moves in a role that no one but the folks of "Friends" could have imagined for him. DeVito's go-for-broke attitude gets him fifth place on this list.

In 1996, well before Charlie Sheen was on the biggest sitcom on TV with "Two and a Half Men" (and then got fired for "winning"), Sheen guest starred on "Friends." It was Season 2, Episode 23, "The One with the Chicken Pox," and Sheen's Ryan comes to see Phoebe and, as the title suggests, gets chicken pox. See, Ryan is a sailor in the United States Navy who spends most of his time on a submarine, only resurfacing every couple of years, at which point he goes to see Phoebe. This time, though, Phoebe, the only friend who hasn't had them as a child, gets chicken pox because of Ross's son. Unfortunately, Ryan hasn't had them either and, when he makes a grand gesture of kissing Phoebe despite the pox, he gets them himself.

This leads to a two-week furlough spent getting over chicken pox with Phoebe. Instead of a romantic time going to places around New York, the couple spends their time in Monica's apartment trying — and failing — not to scratch. They even have their hands taped up with oven mitts to avoid scratching. It's not a noteworthy shore leave for Ryan, but for Sheen, it was a tour de force of comedic talent and timing that ultimately landed him this high on our list of "Friends" guest stars.

Jennifer Aniston married Brad Pitt in 2000, and in 2001, Pitt guest starred on "Friends." In Episode 9 of Season 8, "The One with the Rumor," Pitt plays Will Colbert, a commodities broker who was friends with Ross and Monica in high school. Although Will looks like "Brad Pitt" now, he was 150 pounds heavier in high school and still has some insecurities from that time. That's also why he hates Rachel; she was terrible to him during school. Will and Ross not only had an "I hate Rachel Green" club, but they retaliated by starting the rumor of the episode's title: that Rachel is intersex.

Rachel is horrified by this revelation, although it does explain a lot from her final years of high school. While Ross feels bad about spreading the falsehood, Will feels just fine and continues to hate Rachel years later. While the episode experienced backlash from the intersex community, Pitt put on his best and funniest game face to make sure the episode was top-notch. He was perhaps one of the best-known stars to ever guest on the show, and seeing him and his real-life wife at the time acting at odds together was fun enough to get him to number three on this list. 

Gary Oldman had the thankless task of joining "Friends" during Monica and Chandler's two-part wedding episode at the end of Season 7, but it turns out he was hysterical in his role as Richard Crosby, the actor who stars opposite Joey in a war epic. In Episode 23, he teaches Joey about the power of spitting as an acting technique, and by the end of the episode, the two of them are spitting their way through their scenes. Then in Episode 24, he shows up drunk and proceeds to ruin any chance Joey thought he had of attending Monica and Chandler's wedding — until Joey takes matters into his own hands and sees Richard out of the building.

Richard had several funny bits in the episodes: first, overly pronouncing every syllable he says and excusing it to Joey as enunciation, and then acting drunk and doing things like trying to cut his steak with a very large sword. Oldman excelled as the character and, once again, showed what a chameleon he is, no matter what the role. He was so likable in these two episodes that, even though he's not the main thing people were excited about, he deserves the second spot on this list. 

When Christina Applegate came on in Season 9, Episode 8 of "Friends" as Rachel's sister, Amy, she was spoiled, self-centered, and ... delightful. Amy manages to be completely obnoxious while being nothing less than hilarious, even starting a debate about who would be the best person to raise Ross and Rachel's baby Emma should they die. While Amy is put out that Monica is first in line to get the baby, she's even more put out that Rachel doesn't let her use her Ralph Lauren discount.

Applegate is so funny that she came back for Episode 5 of Season 10, "The One Where Rachel's Sister Babysits" — and if there's one thing the first episode didn't set us up for, it's Amy babysitting. Clearly, Rachel didn't think it through, because she didn't realize that Amy would have Emma's ears pierced.

Whether she is confusing Ross with other versions of Ross (and a guy who runs a falafel cart), finding everything about Emma boring, or generally making everything about her, Amy is a joy — twice. It's a feat that earned Applegate the No. 1 spot on this list.