1. Barry, played by Mitchell Whitfield.
Then: Before there was "The Rachel," there was "The Long Island Rachel," a spoiled daddy's girl engaged to Barry the orthodontist. Except then she ditched him at the altar and fled to Manhattan in her wedding dress, where she bumped into her old high school friend Monica. The rest was Central Perk history.
IRL: Mitchell Whitfield actually auditioned for the part of Ross but was cast as Rachel's jilted fiancé instead. He has since guest-starred on TV shows like CSI and Curb Your Enthusiasm,and does a boatload of voiceover work for video games and animated series like The Legend of Korra and Transformers: Robots in Disguise. He's also editor in chief of a tech website and hosts a radio show on SiriusXM. No word on what happened with Mindy.
2. Paolo, played by Cosimo Fusco.
Then: With her newfound big city freedom, Rachel did what anyone would do: She found a hot foreigner to bone. Rachel and Paolo's relationship irked a pining Ross to no end, but, fortunately for Ross at least, it didn't take long for Paolo to put the moves on Phoebe and get himself banished from the group.
IRL: Italian actor Cosimo Fusco has appeared in films like Angels & Demons and several other German and Italian series. He lives in Rome and is aging very, very well, as Italians often do.
3. David, played by Hank Azaria.
Then: David, the mild-mannered scientist who popped in and out of New York, was a real heartbreaker. After quickly falling in love with Phoebe, he left her to pursue his career in Minsk — which, sure, isn't quite as far away as Yemen but still far enough to make the whole long-distance thing difficult. And this was the '90s, aka pre-Skype. When he finally returned for good, Phoebe had moved on to her (eventual) husband, Mike. Yay, Mike.
IRL: Hank Azaria is a prolific TV, film, and theater actor (you may recognize him from the Night at the Museum series, Ray Donovan, Dodgeball, and Along Came Polly, to name a few), and is best known for his voice work as a slew of characters (like Moe, Apu, and Chief Wiggum) on The Simpsons. He dated Helen Hunt for what seemed like forever and then they got married ... and divorced after a quick minute. What happened there?!
4. Ryan, played by Charlie Sheen (!!).
Then: Another long-distance love, not-so-long relationship for Phoebe, and this time it was a sailor on shore leave who showed up to visit (you know, conjugally) just as she was coming down with a case of the chicken pox. She passed it on to him and they spent two weeks trying to scratch one another's itches. That's commitment and probably good fun — at least when you hit the spot just right. Winning!
IRL: Ryan was played by Charlie Sheen, one of many well-established celebrity cameos. Sheen went on to a long career in TV comedy with Two and a Half Men, before, um, going a little off the rails and anointing himself a tiger-blooded Twitter warrior. We prefer the kinder, gentler '90s Charlie, at least when he's not contagious.
5. Fun Bobby, played by Vincent Ventresca.
Then: Everybody loved Monica's boyfriend, but after a few dates, Monica noticed it was booze (and lots of it) that put the "fun" in Fun Bobby. After gently broaching the subject, Fun Bobby decided to quit drinking, turning him into Sad Bobby. To cope with his new mopey disposition, Monica turned into Drunk Monica.
IRL: Vincent Ventresca has worked steadily since his days on Friends (and he played the douchebro-turned-sadsack in Romy and Michele's High School Reunion alongside Lisa Kudrow and current Jennifer Aniston manpiece Justin Theroux). He'll always be Fun Bobby to us, but he's also widely known for his role on the cult classic The Invisible Man.
6. Danny, played by George Newbern.
Then: What do you do when you come across a yeti in your apartment building? Fog him, of course! And when that yeti shaves his beard and turns out to be pretty cute, well, you date him (if you're Rachel). Despite things looking pretty promising with Danny, the relationship ended after Rachel was weirded out by his touchy-feely relationship with his sister.
IRL: Although we're sure he's a lovely person, George Newbern does play a great creep. He's currently freaking us out as B613 agent and Quinn's on-and-off again boyfriend on Scandal.
7. Roger, played by Fisher Stevens.
Then: With a squad this tight, bringing in any outsider is hard. Why do you think they mostly ended up with each other, after all?! But when that outsider is a psychiatrist and takes pleasure in pointing out your girlfriend's friends' ticks and secret insecurities, well, it's a dating death sentence. When Phoebe told Roger that everyone, like, hated him, he lashed out at the group's codependent tendencies.
IRL: Fisher Stevens has guest-starred on TV shows Elementary and Californication, and in movies like The Grand Budapest Hotel. He's also produced eco-conscious documentaries like The Cove and Mission Blue, and made this celebrity-heavy PSA (which includes Jennifer Aniston and Courtney Cox, don't you know) about dolphins in captivity.
8. Joshua, played by Tate Donovan.
Then: Rachel was demoted to a personal shopper position at Bloomingdales and was ready to quit when she met Joshua, a crushworthy divorcée. She tried several ways to ask him out (without actually asking him out) and eventually the two started casually dating … But he was quickly scared off by what appeared to be Rachel's obsession with getting serious.
IRL: Tate Donovan was Jennifer Aniston's boyfriend at the time of filming — he's one of many real-life partners who made it onto the show. Others include Julia Roberts (who dated Matthew Perry), David Arquette (married to Courtney Cox at the time), and Brad Pitt. OK, let's not go there.
9. Ethan, played by Stan Kirsch.
Then: This storyline probably wouldn't fly on TV today (although, hello, Ezra Miller in Trainwreck), but it did seem funny at the time. Monica started dating a younger guy, only to find out, post-deflowering him, that he's really young. As in "can't stay over, I have a calculus quiz first period tomorrow and I need to study" high school young. Yeah, there's a reason they called this episode, "The One With the Ick Factor."
IRL: Actor Stan Kirsch just looked boyish at the time — he was actually born in the '60s, making him perfectly legal, thank you very much. He continues to work as an actor and runs his own performing arts school in L.A.
10. Duncan, played by Steve Zahn.
Then: While we like to think of Ross as "the divorce guy," Phoebe also had a significant significant other. When a cute ice dancer showed up looking for her, because that's the sort of thing that would happen to Phoebe, the gang was shocked to find out that (1) she was married and (2) she legit loved her husband — even though he was gay. And Canadian. When you think about it though, this is quintessential Buffay brilliance (and not shocking at all). Unfortunately for Phoebs, Duncan resurfaced only to request an end to their green card marriage so he could marry — shocker — another woman.
IRL: Steve Zahn has appeared on Modern Family, and in films including Dallas Buyers Club and the Diary of a Wimpy Kid trilogy. He remains close friends with Jennifer Aniston (no pun intended) and, fun fact, once upon a time was almost cast as Breaking Bad's Walter White.
11. Dr. Richard, played by Tom Selleck.
Then: After bumping into longtime family friend Richard at a party, Monica became, in the words of Phoebe, a smitten kitten. Despite their 21-year age difference (and the fact that he was friends with her parents, and a grandpa), Richard and Monica embarked on a long-term relationship that only ended when he decided he wasn't up for having more children. He tried to reconcile later on, but she'd already moved on to Chandler.
IRL: Tom Selleck's mustache has been a Hollywood mainstay for decades, from his days on Magnum, P.I. to classic films like 3 Men and a Baby to TV series like Las Vegas and Blue Bloods.
12. Mark, played by Steven Eckholdt.
Then: After months of will-they-or-won't-they tension, Ross and Rachel were happily dating when along came Mark, a fashion executive who was more than happy to help Rachel advance in the fashion merchandising business. Ross's jealousy over this new friendship led to the epic "we were on a break" fight and bad breakup. Eventually Mark admitted that he did have a crush on Rachel and the two dated, albeit very briefly. He resurfaced in the last season to hook Rachel up with a job at Louis Vuitton in Paris. (It's never explained how or why this guy could pass out fashion jobs like candy, because yeah, that doesn't happen.)
IRL: Steven Eckholdt went on to work on The West Wing, The L Word, Bones, and Rizzoli and Isles. According to his IMDb page, his nickname is Mr. Perfect. Bet Ross doesn't think so.
13. Pete, played by Jon Favreau.
Then: After a series of professional mishaps, Monica was struggling to find work as a chef and took a job in a 1950s-themed diner (the one where she was forced to wear a boobtastic uniform). It's there that she met Pete, a regular customer and multimillionaire who took her to Rome for their first date. I mean, where else can you get good pizza? The two got pretty serious, but when Pete decided to devote his energy to, of all things, being a UFC fighter (he's pretty bad at it), Monica broke up with him.
IRL: Jon Favreau played Pete and at that time was famous for making indie films with his buddy Vince Vaughn. (We hold them responsible for "Vegas, baby!") He's gone on to be a successful producer, actor, and director with hits like Elf, Cowboys & Aliens, and Iron Man under his belt.
14. Tag, played by Eddie Cahill.
Then: When searching for a new assistant, Rachel found Tag, a very cute, very young, and very unqualified candidate. Obviously, she hired him immediately; look at those eyes. The two began a workplace affair that Rachel ended when Tag showed up at her 30th birthday on a razor scooter. The shame of it all.
IRL: New York-based actor Eddie Cahill went on to roles in Charmed, Felicity, and Dawson's Creek, and has more recently starred in CSI: New York and Under the Dome.
And 15. Russ, played by David Schwimmer.
Then: After getting into a fight with Ross over a list he made of all her faults, Rachel started dating Russ, a Ross look-alike with a similar, halting way of speaking. Upon realizing the glaring similarities, Rachel dumps Russ (and he moves on to Ross's ex, Julie).
IRL: No surprise here, Russ is Ross — David Schwimmer played both parts, but the credits listed a pseudonym, "Snaro," for the role. We'll see Schwimmer playing Kardashian patriarch Robert Kardashian this fall in American Crime Story: The People vs. OJ Simpson.
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