1. Brad Pitt as Will Colbert
Yes, Brad Pitt—actual Fight Club Brad Pitt—played a guy who hated Rachel Green. In the Season 8 Thanksgiving episode, he shows up as Will Colbert, Ross’s high school buddy who co-founded the “I Hate Rachel Green Club.” The best part? He was married to Jennifer Aniston at the time, making it an inside joke so sharp it practically left a scar. Wearing a chunky sweater and holding a grudge, Will is petty, salty, and completely hilarious. His beef with Rachel escalates into high school confessions and fried food shade. It’s peak Friends energy and a blink-and-you-miss-it Brad cameo that absolutely lives rent-free in our minds.
2. Reese Witherspoon as Jill Green
Long before she was leading Big Little Lies or building an empire of book clubs, Reese Witherspoon dropped into Friends as Rachel’s spoiled little sister, Jill. She breezes into Central Perk in Season 6 in head-to-toe mall chic, wielding a credit card and zero chill. Jill flirts with Ross, steals her sister’s thunder, and drops lines like, “I want to buy a tee-pee!” with total sincerity. The tension is fabulous, and Reese plays bratty with a comedic edge that hinted she’d be dominating screens for decades. Fun fact: she only did two episodes—but her character made enough of an impact that fans still hope for a Green Sisters spinoff. Reese nailed rich-girl meltdown energy before Elle Woods made it cool.
3. Bruce Willis as Paul Stevens
Bruce Willis, action hero and tough guy extraordinaire, showed up on Friends not to fight crime—but to date Rachel and cry in front of a mirror. As Paul Stevens, the overprotective father of Ross’s student-turned-girlfriend Elizabeth, he goes from intimidating to awkward in record time. In one of the show’s funniest visual gags, he gives himself pep talks shirtless and weepy, whispering affirmations like “I’m just a love machine” in a bathroom. His chemistry with Rachel is peak sitcom chaos, and his inability to stay cool around Ross is pure gold. Willis actually appeared in three episodes and reportedly did it for free after losing a bet with Matthew Perry. That’s right—Friends got Bruce Willis for free, and he still stole the scenes.
4. Gary Oldman as Richard Crosby
Gary Oldman—yes, Oscar-winning, Sirius Black-playing Gary Oldman—guest starred in Friends as Richard Crosby, the outrageously over-the-top actor cast alongside Joey on Days of Our Lives. Richard is known for “spitting” his words… literally, showering Joey with saliva mid-scene in the most hilariously disgusting performance ever. His method acting involves a lot of slurring, gesturing, and over-enunciating, which drives Joey completely bonkers. Things escalate when Oldman’s character shows up drunk to set on Monica and Chandler’s wedding day, forcing Joey to juggle groomsman duties and dramatic monologues. Watching Oldman go full soap-opera ham is pure joy. It’s theatrical chaos, and somehow… it works.
5. Aisha Tyler as Charlie Wheeler
Aisha Tyler made history as the first Black actor with a recurring role on Friends, and she absolutely delivered as Charlie Wheeler, the whip-smart paleontology professor who dated both Joey and Ross. She brought brains, beauty, and a no-nonsense attitude to a show full of emotional chaos, holding her own in a sea of neurotic exes and café drama. Charlie was refreshingly confident and grounded, with some of the sharpest one-liners in the later seasons. Tyler’s comedic timing was effortless, and her chemistry with both guys gave the love triangle real depth—until she wisely chose dignity over dysfunction. Plus, she was one of the few guest stars who didn’t fall into the usual ditzy or quirky trope. Honestly? Charlie deserved her own spinoff.
6. Ben Stiller as Tommy (a.k.a. “The Screamer”)
Before he was Zoolander or managing awkward parents, Ben Stiller had a very memorable meltdown on Friends. In Season 3’s “The One with the Screamer,” Stiller plays Tommy, Rachel’s new boyfriend with rage issues so intense it’s almost art. To everyone else, he seems charming—but to Ross, he’s a full-blown fury tornado who yells at theatergoers, ducks, and eventually Chandler. Ben’s unhinged, wide-eyed rants are iconic, especially when he flips out over a chick pooping on his hand. “Step away from the duck!” deserves an Emmy of its own. It’s over-the-top Stiller comedy at its finest—and somehow fits perfectly into the Friends universe.
7. Anna Faris as Erica
Anna Faris showed up in Season 10 as Erica, the sweet-but-ditzy birth mom to Monica and Chandler’s future twins, and honestly? She crushed it. With perfect comedic timing and a knack for wide-eyed confusion, she navigates a classic Friends misunderstanding thinking Chandler is a doctor and Monica is a reverend. She’s earnest, slightly chaotic, and just vulnerable enough to make you root for her. Her scenes added real heart to the final season and gave Monica and Chandler their long-awaited parenting arc. Plus, her delivery of “I like that you’re not blond. Blonds are not trustworthy” is legendary. Anna’s role might’ve come late in the series—but it was unforgettable.
8. Sean Penn as Eric
Yes, that Sean Penn—Oscar-winner, method actor, world-class brooder—showed up in Season 8 wearing a giant solar system costume. He played Eric, the fiancé of Phoebe’s twin sister Ursula (who had been lying to him… obviously). When Eric meets the real Phoebe, sparks fly and confusion ensues because identical twins + chaos is always a Friends staple. Watching Penn try to play adorkable in Halloween face paint is surprisingly delightful. You can tell he’s trying really hard to keep up with the sitcom pace, and that’s part of the charm. Two episodes, one mix-up, and one deeply uncomfortable turtle neck later, Eric is history—but what a weird ride it was.
9. Jon Favreau as Pete Becker
Before he was directing Marvel blockbusters or voicing a beloved Mandalorian sidekick, Jon Favreau played Monica’s eccentric millionaire boyfriend Pete in Season 3. He’s rich, overenthusiastic, and casually buys her a restaurant because nothing says romance like a surprise career pivot. Pete’s dream of becoming the Ultimate Fighting Champion (yes, really) takes their relationship from “fairy tale” to “emergency room” pretty fast. Watching Monica try to support his bizarre dream is both hilarious and deeply cringey. He gets pummeled in the ring while Monica cheers in horror—and somehow, we still feel bad for him. It’s the kind of offbeat, over-the-top arc Friends loved—and Favreau went all in.
10. Winona Ryder as Melissa Warburton
Winona Ryder had a blink-and-you’ll-gasp cameo in Season 7 as Melissa, Rachel’s sorority sister who once kissed her at a party. Rachel tells Phoebe the story and claims it meant nothing, only to be confronted by Melissa—who, it turns out, has been harboring feelings ever since. Winona delivers a masterclass in emotionally unhinged grace as she insists the kiss meant everything and tries to reignite the spark. The best part? The kiss happens again, and Melissa deadpans, “And I’m straight… I just made out with my college roommate.” Rachel’s face = priceless. It’s chaotic sapphic comedy, delivered by one of the ‘90s biggest stars—and we’re still not over it.
11. Alec Baldwin as Parker
Alec Baldwin showed up in Season 8 as Parker, Phoebe’s hyper-enthusiastic, scenery-loving, compliment-hurling boyfriend. He’s so aggressively positive it borders on performance art, delivering lines like, “This is the most beautiful cake I’ve seen in my life!” with Oscar-level intensity. At first, it’s charming—then it gets… a lot. Even Phoebe, the quirkiest of the bunch, can’t handle his relentless awe over coat racks and traffic cones. Baldwin nails the over-the-top energy with a manic smile and jazz hands, like if a motivational speaker drank six Red Bulls. It’s hilarious, weird, and very, very Friends.
12. Christina Applegate as Amy Green
Before she was earning Emmy nominations for Dead to Me, Christina Applegate was earning laughs (and an actual Emmy!) for playing Rachel’s self-absorbed sister Amy. She appears twice and instantly causes chaos—calling Emma “Ella,” assuming Ross is a gynecologist, and asking if her niece’s ears are “too big to ever wear earrings.” Christina delivers every line with the kind of clueless confidence that makes you want to both hug and throttle her. She’s the perfect foil to Rachel’s slightly-more-evolved energy, and the sisterly bickering is sitcom gold. If sarcasm were an Olympic sport, Amy Green would have medals.
13. Susan Sarandon as Cecilia Monroe
Yes, Oscar-winner Susan Sarandon once graced Friends as Cecilia Monroe, a soap opera legend whose character on Days of Our Lives is being replaced… by Joey. In Season 7, Joey’s character “Dr. Drake Ramoray” is getting a brain transplant, and Cecilia is not having it. Sarandon struts onto the set in full diva mode, oozing glam and delivering cutting barbs with delightful drama queen flair. She and Joey end up sharing a passionate kiss that weirdly kind of works. The best part? She later passes her legacy (and possibly her brain?) to him in true soap fashion. It’s the most dramatic thing to ever happen in a room full of fake hospital equipment.
14. Charlie Sheen as Ryan
Charlie Sheen shows up in Season 2 as Ryan, a Navy man on shore leave who’s in a long-distance, infectious-disease-filled romance with Phoebe. Their brief but hilarious reunion involves both of them catching chickenpox and trying (unsuccessfully) not to scratch while snuggling. Sheen delivers a surprisingly sweet performance, covered in oven mitts and doting like a lovesick porcupine. It’s delightfully bizarre, even by Friends standards. Watching two adults in full-body rashes make out while resisting the urge to claw their own skin off? Equal parts funny and disturbing. Classic Charlie Sheen chaos meets peak Phoebe weirdness—and we wouldn’t have it any other way.
15. Hank Azaria as David
Long before voicing half of Springfield on The Simpsons, Hank Azaria played David the Scientist Guy—Phoebe’s nerdy, lovable on-again, off-again boyfriend. He first appears in Season 1 as the sweet but slightly clueless physicist who moves to Minsk (because apparently, that’s what physicists do), leaving Phoebe heartbroken. He pops up several times throughout the series, each return full of awkward timing and doomed romantic tension. David is so sincere, you kind of root for him—even when he competes with Mike (Paul Rudd) for Phoebe’s heart. Azaria nails the tragic dork vibe with charm and vulnerability. We still wonder if David ever made it big in Belarusian science circles.
16. Freddie Prinze Jr. as Sandy
Freddie Prinze Jr. shows up in Season 9 as Sandy, the sensitive male nanny who melts hearts—and makes Ross wildly uncomfortable. With his lullaby guitar skills and emotional intelligence, he’s basically a preschooler’s dream and a sitcom dad’s worst nightmare. Freddie leans all the way into the soft-boy energy, gently telling stories and demonstrating baby-soothing techniques that terrify Ross’s fragile masculinity. It’s a sharp, hilarious take on gender roles, and Freddie plays it perfectly straight. Bonus points for making Rachel cry with a bedtime story. Honestly, Sandy deserved his own spinoff—he was that good.
17. Denise Richards as Cassie Geller
Denise Richards appeared in Season 7 as Ross and Monica’s cousin Cassie, whose good looks send everyone into a spiral. With her flowing hair and slow-motion entrance, she quite literally turns heads—and causes Ross to have one of his most cringeworthy moments ever. Rachel can’t stop staring, Chandler forgets how to form sentences, and Ross… well, he tries to kiss her. Yes, his cousin. Richards plays it cool and confident, completely unbothered by the chaos she causes. The whole episode feels like a slow-motion car crash—with perfect hair. It’s awkward, it’s hilarious, and it’s one of the boldest guest arcs on the show.
18. Jeff Goldblum as Leonard Hayes
Jeff Goldblum shows up in Season 9 as a theatrical big shot auditioning Joey for a role in a stage play. He’s eccentric, intense, and gives off major “method actor meets yoga guru” vibes. In a classic Friends twist, Joey’s audition only works when he drinks too much water and is forced to pee—which Goldblum interprets as artistic vulnerability. Goldblum’s signature stammer and over-enunciated praise (“You… were… magnificent!”) take the whole scene to the next level. It’s peak absurdity, and somehow totally believable that this guy would cast Joey. If Jeff Goldblum told you your panic pee was powerful? You’d believe him too.
19. Rebecca Romijn as Cheryl
Before she was Mystique or a real-life supermodel, Rebecca Romijn played Cheryl, Ross’s date who turns out to be an absolute disaster. On the surface, she’s gorgeous and charming—until Ross discovers her apartment is a landfill. We’re talking pizza boxes on the floor, clothes everywhere, and something that may or may not be alive under a pile of laundry. When Ross tries to gently mention the mess, Cheryl doesn’t even flinch—she just invites him to sit on a questionable surface. Watching Ross, king of cleanliness, squirm in horror is sitcom gold. Rebecca plays it straight-faced, chaotic, and totally unforgettable.
20. Danny DeVito as Roy “the Stripper”
In one of the most unexpected and hilarious cameos, Danny DeVito shows up in Season 10 as Roy, the world’s most unlikely male stripper. Hired last-minute for Phoebe’s bachelorette party, Roy is short, sweaty, and wildly committed to his art. The friends are horrified at first, but DeVito’s performance is so enthusiastic and over-the-top, it becomes oddly endearing. He dances, he weeps, and he delivers one of the most awkward lap dances in television history. It’s a masterclass in physical comedy and self-deprecation. Only Danny DeVito could make you feel emotional for a guy in tearaway pants.
21. Kristin Davis as Erin
Kristin Davis made a one-episode splash as Erin, Joey’s brief love interest who the rest of the gang absolutely adores. In Season 7, Erin charms Monica, Chandler, and Phoebe so completely that they’re ready to make her a permanent fixture—until she realizes Joey isn’t actually that into her. Davis brings her signature sweetness and confidence to the role, making it genuinely painful when she decides to walk away. It’s the rare Friends guest arc where everyone likes the new person except the person dating them. The episode ends with the group mourning a breakup that technically wasn’t even theirs. Honestly, Erin deserved better—and maybe her own spinoff.
22. Tom Selleck as Dr. Richard Burke
Tom Selleck’s Dr. Richard Burke is the mustachioed, motorcycle-riding ophthalmologist who stole Monica’s heart—and honestly, most of the audience’s too. Debuting in Season 2, Richard is Chandler and Joey’s idol-turned-competition, and Monica’s older, unexpectedly perfect boyfriend. Selleck oozes charm, class, and dad-energy in a way that somehow works, even when the age difference raises some eyebrows. Their relationship had real emotional weight, and his goodbye? One of the show’s saddest. That mustache held a thousand feelings. And when he returns in later seasons to mess with Monica and Chandler’s storyline? Classic sitcom tension with premium nostalgia.
23. George Clooney as Dr. Michael Mitchell
Before he was saving lives on ER or sipping Nespresso in a Tuscan villa, George Clooney guest-starred on Friends as a dreamy doctor named Michael Mitchell. In Season 1, he and Noah Wyle played ER doctors who go on a double date with Monica and Rachel—pretending to be each other to dodge insurance drama. The whole setup is chaotic, hilarious, and peak 90s crossover energy. Clooney plays his role with his signature wink-and-a-smirk charm, delivering lines with that cool-dad energy that made him a star. Seeing him in a Friends living room instead of a hospital was surreal—in the best way. It was a brief but unforgettable cameo that made fans everywhere go, “Wait—is that George Clooney?!”
24. Jon Lovitz as Steve
Jon Lovitz guest-starred twice as Steve—the guy who proves that some people should never be invited over for dinner. In his first appearance, Steve shows up high as a kite to a job interview with Monica and immediately starts raving about her “mootant” crustaceans. He’s loud, inappropriate, and delivers every line with Lovitz’s signature dry sarcasm. Years later, he returns (miraculously sober) on a double date and is just as judgmental, proving sobriety doesn’t always fix everything. Monica’s face during both encounters is priceless. If you needed proof that chaos can wear a suit, Steve was it.
25. Jennifer Grey as Mindy Hunter
You might not recognize her at first glance, but yes—that was Dirty Dancing’s Jennifer Grey playing Rachel’s best friend-turned-fiancé-thief in Season 1. As Mindy Hunter, she reconnected with Rachel to ask her to be maid of honor… for her wedding to Barry, Rachel’s ex-fiancé. Grey played Mindy with a hilariously soft-spoken cattiness, delivering backhanded compliments and wide-eyed betrayal like a sitcom ninja. Her scenes with Jennifer Aniston are classic early-season awkwardness, complete with pastel bridesmaid dresses and emotional whiplash. Fun fact: Grey only appeared in that one episode—and the role was later recast in Season 2 with a different actress. Which means you didn’t forget she was on Friends… you just got Mandela Effect-ed.
26. Jason Alexander as Earl
In one of the show’s darker but more heartfelt cameos, Jason Alexander appears in Season 8 as Earl, an office worker Phoebe calls while trying to sell toner. Instead of hanging up, he tells her he’s suicidal—and she ends up spending the episode trying to cheer him up. Alexander plays against type here: quiet, sad, and a little snarky, giving the episode a surprisingly emotional core. His deadpan delivery makes Phoebe’s frantic optimism shine even more. The result is one of the most unexpected deep cuts of the series. Seinfeld may have made him famous, but Friends showed his heart.
27. Julia Roberts as Susie Moss
Julia Roberts played Susie “Underpants” Moss in Season 2, and yes—it was just as unforgettable as it sounds. She appears as a glamorous makeup artist who reconnects with Chandler, only to seduce him… and then completely humiliate him. Turns out, Susie is still mad about Chandler lifting her skirt in grade school, and now it’s payback time. Watching Julia Roberts giddily trick Chandler into stripping in a restaurant bathroom is deliciously devious. The best part? She pulls it off with total charm and zero remorse. Julia was already a megastar, but this role proved she could crush sitcom comedy just as hard as rom-coms.
28. Brooke Shields as Erika Ford
Brooke Shields made one of the most chaotic and hilarious cameos as Erika, the overly obsessed fan of Joey’s soap opera character, Dr. Drake Ramoray. She genuinely believes the character is real and that Joey is a brain surgeon who’s been cheating on her with that “slutty nurse.” Shields plays unhinged with elegance—teetering between adoration and total delusion with every bat of her eyelashes. Joey tries to explain it’s just a show, but Erika’s grip on reality is softer than her hold on Joey’s arm. Brooke steals every scene with her wildly exaggerated reactions and soap opera-level dramatics. It’s the kind of cameo that makes you shout, “Wait—was that Brooke Shields?!”
29. Jean-Claude Van Damme as Himself
The Muscles from Brussels showed up as himself in Season 2’s two-part Super Bowl episode, and it’s as weird and wonderful as you’d hope. Monica and Rachel both try to score a date with him on a movie set, leading to a mini war of flirting and sabotage. Van Damme plays it surprisingly well, leaning into his action-star image with a clueless charm and some hilariously awkward lines. Watching him hit on both women while name-dropping “three-way” like it’s small talk is peak sitcom absurdity. He’s suave, ridiculous, and weirdly perfect for the Friends universe. If you forgot this cameo existed… you’re welcome.
30. Greg Kinnear as Dr. Benjamin Hobart
Greg Kinnear played the manipulative and wildly awkward ex-boyfriend of Charlie (Aisha Tyler) in Season 10. Dr. Hobart just so happens to be the head of a grant Ross is applying for, and naturally, chaos ensues. Kinnear plays him with a weird blend of passive-aggression and desperation, offering Ross the grant if he’ll agree to break up with Charlie. He spirals from charming to unhinged in less than three scenes, and every moment is hilariously tense. Watching Ross navigate a moral crisis while Kinnear sips tea and grins like a villain is comedy gold. If you ever wanted to see Greg Kinnear weaponize academia, this is it.
31. Paul Rudd as Mike Hannigan
Paul Rudd didn’t just guest star—he low-key became everyone’s favorite late-game MVP. Introduced in Season 9 as Phoebe’s blind date (thanks to Joey panicking and yelling “Mike!”), Mike Hannigan turns out to be charming, awkward, and exactly what Phoebe needed. From accidentally revealing he plays air piano to dueling with David (her sciencey ex), Rudd brings just the right mix of sincerity and goofball magic. Fans quickly fell in love with him, and by Season 10, he was a full-blown Friend-in-law. His proposal scene? Swoon-worthy. And let’s be honest—Phoebe marrying anyone other than Paul Rudd would’ve been a crime against television.
