30 Best ‘Friends’ Guest Stars, Ranked

Although beloved for her recent work on “The White Lotus,” Jennifer Coolidge isn’t the first “Friends” guest star to come to mind. She popped up in the final season when the B-stories often got swallowed up by the show tying up a decade of loose ends. Her role as a vain former friend of Monica (Courteney Cox) and Phoebe’s (Lisa Kudrow) also wasn’t the most inspired character, except for the little dance she does for a bewildered Chander (Matthew Perry). That being said, her appearance gets credit for one thing –– Cox’s impeccable line-reading of her character’s name, Amanda Buffamonteezi.

A year before “Grey’s Anatomy” premiered, Ellen Pompeo played Missy Goldberg, a former college classmate and crush of both Chandler and Ross (David Schwimmer). When they encounter her at a college reunion, their rivalry resurfaces and unleashes a wave of secrets, including the revelation that what Ross thought was his first kiss with Rachel after a college party turned out to be his sister, Monica. Oh, those Gellers!

When Rachel (Jennifer Aniston) flies to London to stop Ross from marrying Emily (Helen Baxendale), she subjects her seatmate, a pre-”House” Hugh Laurie, to their convoluted love story, much to his chagrin. Laurie is doing what he does best –– disgruntled disinterest –– and tells her the last things she wants to hear in the middle of her sweeping romantic gesture: She shouldn’t be crashing the wedding and they were on a break.

Did you know that “Friends” is technically a spinoff of “Mad About You?” In the ‘90s sitcom starring Paul Reiser and Helen Hunt, Kudrow appeared in 24 episodes as Ursula, an ineffective waitress at Riff’s, the restaurant where the “Mad About You” characters hang on the show. Ursula, of course, is the twin sister of Phoebe. When “Friends” became an instant hit, Helen Hunt and her “Mad About You” costar Leila Kenzle popped in for one scene at Central Perk, where they confused Phoebe for Ursula in a fun nod for those who understood the connection.

One of the delights of “Friends” was the ever-evolving backstory for Phoebe, who seemed to have lived a dozen lives before we met her in Season 1. One of those lives involved marrying a gay Canadian ice skater who needed a green card to continue living in America. But Steve Zahn comes back into her life wearing a matador’s outfit to confess that he’s not gay. He’s straight, he’s in love and he needs a divorce.

Things that were considered funny on TV in 2001 don’t always age well in hindsight, and Kathleen Turner’s role as Chandler’s transgender parent is one of them. As Monica and Chandler’s wedding approaches, she pushes him to make amends with his father, who identifies as a woman after coming out in his childhood. Now performing as a drag artist named Helena Handbasket in Las Vegas, they visit her show, and boy does Turner put on the ritz. It’s a fun performance marred 20 years later by the show’s less-than-nuanced jokes about gender identities and pronouns.

Another storyline that doesn’t sit well all these years later is Freddie Prinze Jr.’s turn as a male nanny hired by Rachel and Ross for their daughter, Emma. Rachel loves his hands-on and educational techniques with Emma, but Ross can’t get over that he is a man working as a nanny. Prinze Jr. eventually changes Ross’ mind, but not before he offends everyone involved in that special way that Ross is wont to do.

An overly emotional stripper beaten down by years in the business and bad knees is not what most want out of their bachelorette parties, but it was perfect for Phoebe Buffay. The zany energy that has become Danny DeVito’s brand in the past 20+ years was on full display as he tried to awkwardly bump and grind his way through the motions, until he couldn’t hold back his tears anymore. But it is legitimately a thrill to watch him pull out all the stops once Phoebe convinces him to wipe away the tears and finish his performance.

As Joey (Matt LeBlanc) wrestles with the reality that Monica and Chandler are moving to the suburbs to raise their children, he has a heart to heart with the wise-beyond-her-years little girl living in the house they want to buy. Dakota Fanning was the prime of her early career when she appeared in this one scene with Joey, reminding him that he won’t lose his friends even if he lets them go. The fact that she may or may not have been a ghost is beside the point!

In Rachel and Ross’ early days of dating, the gang teases them about their “freebie” lists, a.k.a. the celebrities they are allowed to sleep with if the opportunity ever presents itself. Unfortunately for Ross, he took the assignment too seriously. When Isabella Rossellini, one of his candidates who didn’t make the final cut on the laminated list, walks into Central Perk, she shuts him down for excluding her.

Marlo Thomas appeared only a few times as Rachel’s pretentious mother Sandra, but her funniest turn came in Season 8 during Rachel’s baby shower. When party planner Monica invites everyone but the grandmother-to-be, she hilariously spends the entire shower trying and failing to suck up to a dismissive Sandra for forgiveness.

Chandler’s mother Nora is a famous romance author who comes into town after a whirlwind book tour, and wants to be more involved in her estranged son’s life. But she doesn’t help her case when she seduces his best friend Ross, making for an icy reunion. Her Season 1 appearance was fun, but Morgan Fairchild’s later appearances were largely centered on her contentious relationship with her ex-husband and Chandler’s father, who now identifies as a woman.

When Ross accidently knocks a Brown Bird Scout down a flight of stairs with his tennis backhand, he has to step in to try and sell enough cookies to send her to space camp. Most of Mae Whitman’s scenes are bed-ridden with a broken leg, but she is unbelievably endearing and incredibly skilled at nailing the punchline. But the highlight is her big grin when Ross fails to get her to camp so he, Chandler and Joey create an at-home rocket simulation. It’s no wonder Whitman was one of the most sought-after child actors of her generation.

In a clever bit of synergy for NBC’s Must-See TV lineup, “ER’s” hunky doctors George Clooney and Noah Wyle appeared as two different doctors who take Rachel and Monica out on a double date after Rachel injures her leg. But an insurance issue forces them to switch names, and they have to keep up the charade on the date. When a disagreement over which woman gets which doctor escalates, they start airing each other’s dirty secrets in front of their increasingly uncomfortable dates who just wanted a normal night away from the hospital.

To Joey’s delight, the one woman with whom Rachel had a romantic experience in college happens to stroll into Central Perk in this Season 7 episode. Winona Ryder is so often typecast as the Goth type she played in “Beetlejuice,” so seeing her play Melissa, a party planner plastered in pink, was a real joy. She is genuinely funny here, especially when Rachel tries to jog Melissa’s memory of their kiss by planting another on her –– only for Melissa to declare her love for her sorority sister.

Coming off three “Scary Movie” films, Anna Faris pivoted hard to play Erica, an otherwise wholesome Christian girl who gets pregnant and chooses Monica and Chandler as her baby’s adoptive parents. A universe away from the gross-out “Scary Movie” franchise, Faris has the distinction of being the last major guest star in the show’s run, and she closed it out on a high note. Her naive outlook on the world gave Monica and Chandler someone to care for before they all get the surprise of a lifetime when she unexpectedly gives birth to twins.

As the big celebrity hook in the first installment of the show’s star-studded post-Super Bowl episodes, Brooke Shields plays a “Days of Our Lives” fanatic who believes Joey is really his character, Dr. Drake Ramoray. Joey sleeps with her anyway, making it harder to sever ties when she suspects he’s cheating on her with one of the characters on screen. Luckily, his friends are there to literally throw cold water on the situation and create an elaborate story that he’s actually Drake’s evil twin, Hans, to run her off.

Joey’s grand return to “Days of Our Lives” as Dr. Drake Ramoray comes courtesy of a brain transplant, the donor for which doesn’t know it is happening. Joey accidentally breaks the news to veteran actress Cecilia Monroe that her character is unceremoniously being killed off the show. To do justice to Cecilia’s work, he convinces her to train him in her character’s extravagant mannerisms — and share in a brief romance. Sarandon clearly had a blast with the part, stage slapping both Joey and her real-life daughter Eva Amurri to great effect.

We count Giovanni Ribisi and Debra Jo Rupp’s characters Frank Jr. and Alice as one because there are very few instances where they aren’t together. Phoebe is initially hesitant to support her younger brother’s unorthodox relationship with his former teacher, but their genuine love and aggressively physical affection for each other was both undeniable and sometimes hard to watch. Phoebe carrying triplets for them made their sweet romance even more heartwarming.

While working at a 1950s-themed diner after her chef career briefly implodes, Monica initially rebuffs the advances of one of her frequent customers. But Jon Favreau’s charming Pete is persistent, and eventually convinces her to a date. Before long, she falls for him, but there’s one thing standing in their way. He is a tech millionaire with a death wish to become a mixed-martial-arts fighter, which just happens to be the one thing he isn’t good at.

Joey gets the opportunity of a lifetime working alongside Gary Oldman’s pedantic stage actor Richard Crosby in a World War II movie, but the excitement quickly wears off when he learns he excessively spits when he delivers dialogue. To make matters worse, he comes to set staggeringly drunk on the day of Monical and Chandler’s wedding, making it nearly impossible for Joey to make it in time to officiate. Not that we would ever doubt his talents, but Oldman is remarkably good at this brand of cartoonishly wacky drunk.

Some of the best guest spots in the series were short and sweet. Like this one with two of the greatest working comedians of their time, Billy Crystal and Robin Williams. They show up on a busy day at Central Perk and ask if they can share the gang’s infamous orange couch. But as soon as they scooch in, they launch into an emotional chat about Williams’ wife having an affair with a man who turns out to be Crystal. The telenovela drama of it all, in one scene no less, was hilarious and the perfect cameo.

The first of Rachel’s sisters to show up at her door was Jill, a self-absorbed interloper who comes to town hoping to follow in her sister’s footsteps after being cut off by daddy. But she didn’t take to cost-cutting measures as well as Rachel, and even defies her sister’s authority by trying to date Ross. Reese Witherspoon’s current on-screen partnership with Aniston on “The Morning Show” makes this guest arc even more fun to revisit.

Rachel gets more than she bargained for when she starts seeing Bruce Willis’ character Paul, the father of Ross’ college-aged girlfriend. At first, he’s just a handsome, successful lawyer who also happens to ruffle Ross’ feathers. But when they go away for the weekend, Rachel’s insistence that he be more open with her bursts a dam of repressed emotions that results in his endless weeping. Him curled up in a ball in her lap was a hilarious sight from John McClane himself. Surprisingly, Willis is one of only two guest actors to take home Emmys for the show.

Oh what could have been if Hank Azaria’s shy chemist David hadn’t gone to Minsk. When they meet at Central Perk, Phoebe is immediately taken with David’s sheltered, nerdy charisma. Spending his days with his nose in a beaker, he likes how unapologetically she walks through the world. But a research opportunity abroad ends their story before it begins. When he returns later in the series, they could never quite get the timing right.

Landing rom-com queen Julia Roberts was a huge get for “Friends” in its second season, and they didn’t waste her starpower. As a makeup artist on the set of “Outbreak,” she is thrown headfirst into a steamy hookup with Chandler, with whom she went to elementary school. Beguiled by her attention, Chandler obliges her every request, including wearing women’s underwear to dinner. When she lures him into the bathroom under the pretense of sex, she leaves him with nothing but the underwear to humiliate him. Turns out, America’s Sweetheart was out for revenge after Chandler pulled up her skirt in school and showed the school her own underwear. As they say, revenge is best served cold — and 20 years later.

The media frenzy covering Jennifer Aniston and Brad Pitt’s marriage perhaps reached its apex with this wickedly funny episode in which they play adversaries from high school reunited over an awkward Thanksgiving dinner. Pitt plays Will, a former classmate of Rachel, Ross and Monica’s who hated Rachel’s popularity in high school. So much so that he founded the “I Hate Rachel Green Club” with Ross, who was secretly pining over her. Watching the then-married couple go at each other was a brilliant move. Their chemistry and good looks were so off the charts in this episode, it was like staring into the sun.

Monica’s love life wasn’t in great shape in the early seasons of the series, but like Phoebe and David, there was one person that always had us wondering, “What if?” Tom Selleck’s ophthalmologist Dr. Richard Burke may have been older than her (he played golf with her dad!), but few people understood and accepted Monica like he did. Selleck’s empathetic and sexy presence was magnetic. And while we wouldn’t trade Moncia and Chandler for anything, the stoic shadow of Richard loomed large over their story.

Putting Paul Rudd on this list may be a little unfair to some of the other celebrities who had only a precious few scenes on “Friends.” But who doesn’t love his goofy piano player, Mike? In the last two seasons, his burgeoning love story with Phoebe is among the most rewarding things the show ever did. Phoebe’s eccentric personality was never going to be for everyone, but that’s OK because it was perfect for Mike. Rudd has done some over-the-top things in his career, but his finely tuned performance as Mike remains one of his best roles.

Despite being in only two episodes at the tail end of the series, Christina Applegate stands as the epitome of what a great “Friends” guest star could be. As Rachel’s other vapid sister Amy, she is appropriately narcissistic and incredibly funny in her narrow view of the world. But wanting more purpose in life, she lobbies to be the guardian of her Rachel and Ross’ daughter Emma should anything happen to them. When she realizes she is far down the list of responsible adults who would take over parenting duties, she and Rachel spiral into a childish fit (featuring some incredible physical comedy!) that shatters her chances at guardianship and Monica’s precious wedding China. Both of her episodes are among the best in the show’s later years, and Applegate is a riot from start to finish. An Emmy-winner for the role, she is one of our greatest comedic actors — and “Friends” knew exactly how to showcase it.