When Stars Split the Rent: Celebs Who Used to Be Roommates

Even the most famous celebrities struggled before making it big in the cut-throat entertainment industry. In order for these aspiring performers to pay their bills, they saved some cash by getting a roommate. Believe it or not, before they were rich and famous, splitting rent was a good way to keep food on the table until catching their big break!

Milo Ventimiglia on the red carpet in 2008 / Emma Stone on the red carpet in 2008 / Danny DeVito on the red carpet in 2008
Photo by Matt Baron, BEI, Shutterstock / Eric Charbonneau, Shutterstock / Matt Baron, BEI, Shutterstock

Some of these now-famous duos met on college, on set, or wandering around Hollywood looking for an opportunity. Before these talented stars had marble flooring and infinity pools in their lavish mansions, they had a typical roommate life: eating ramen, mismatched furniture, and trying to save as much money as they could. Everybody’s got to start somewhere. Wait until you see why Raven Symone’s roommate was never home. Spoiler Alert: The answer won’t surprise you.

You probably didn’t know that these celebrities used to be roommates.

Lea Michele and Dianna Agron

In 2009, Lea Michele and Dianna Agron moved in together while working on the hit Fox show Glee. On-screen, their characters were enemies, but, in real life, the co-stars were good pals. Michele commented that the roomies never brought any work drama back to their apartment.

Dianna Agron and Lea Michelle on the red carpet posing together goofily
Photo by Gregory Pace / BEI / Shutterstock

Back when they were living together, Michele told New York Magazine, “We have these smackdowns at work and come home and are like ‘Wasn’t it so funny when we were fighting today? Let’s make cookies!’ It works out.” Living with friends isn’t easy, but these two had a great dynamic, and it worked.

Eddie Redmayne and Jamie Dornan

In 2008, Jamie Dornan and Eddie Redmayne moved in together while waiting for their big breaks. Way before Eddie was an Oscar winner and Jamie starred in Fifty Shades of Grey, the struggling actors shared both an apartment and an agent. Dornan spoke about their living situation with James Corden: “We were both very desperate. It was slim pickings for work, and you all go to the same auditions.”

Eddie Redmayne and Jamie Dornan posing on a grey brick street
Source: Pinterest

Eddie Redmayne also reminisced about his roomie days on Good Morning America saying that “One of the amazing things about living with Jamie, is it’s basically like living with a puppy because he has more energy than any human you’ve ever met.” I’m loving this bromance.

Matt Damon and Ben Affleck

It’s pretty well-known that A-listers Ben Affleck and Matt Damon are good friends, but did you know that they lived together while writing their Oscar-winning screenplay for 1997’s Good Will Hunting? In 1999, Affleck told Playboy that the buds lived in a house in Venice Beach, but they had to move after running out of cash.

Ben Affleck and Matt Damon on the red carpet holding their Golden Globe awards in 1998
Photo by Bei / Shutterstock

“We lived in Glendale and Eagle Rock, and we lived in Hollywood, West Hollywood, Venice, by the Hollywood Bowl, all over the place,” he explained. “We’d get thrown out of some places, or we’d have to upgrade or downgrade depending on who had money.” Obviously, money is the least of their worries now.

Lauren Graham and Connie Britton

Before becoming the beloved TV stars that we all know and love, Lauren Graham and Connie Britton roomed together. But, at one point, the roomies couldn’t even afford furniture. “We lived in an empty house that we weren’t supposed to be living in,” Graham revealed to Andy Cohen, “we had no furniture, and all we ate were Rice Krispies Treats.”

A selfie of Connie Britton and Lauren Graham
Source: Instagram / Lauren Graham

Yum! I love Rice Krispy Treats! That’s pretty much all I ate back in college, so I get it. In 2015, in honor of Britton’s birthday, the Gilmore Girls’ actress posted a picture of her with her former roommate with the caption, “Let’s all party like it’s 1999!” If only we could go back to the good old ‘90s.

Wes Anderson and Owen Wilson

Director Wes Anderson and actor Owen Wilson have worked together on several occasions. The two collaborated on movies such as The Royal Tenenbaums, Rushmore, The Darjeeling Limited, and Fantastic Mr. Fox. You would think that these two met in the very exclusive Hollywood circuit, but that wasn’t exactly it.

Wes Anderson and Owen Wilson at an event together
Photo by Matt Baron / BEI / Shutterstock

Way before they built a professional partnership, they had a roommate relationship. The actor and director moved in together at the University of Texas. That’s where they co-wrote the 1996 film Bottle Rocket. Anderson and Wilson aren’t the only roommates who paved the road to success by writing a movie together while cohabitating.

Ed Westwick and Chace Crawford

We all recognize these Hollywood heartthrobs from the hit teen drama Gossip Girls. The two were best pals on-screen and apparently off-screen too. The co-stars shared an apartment in New York during the show’s first season. Luckily, working and living together didn’t harm their friendship.

Ed Westwick and Chase Crawford on the red carpet together in 2015
Photo by Jim Smeal / BEI / Shutterstock

In fact, their living arrangements were really convenient for Chase and Ed. Crawford spoke about living with Westwick during an interview: “We got along and figured it would be a smart move financially. And really, it was also just kind of out of laziness.” Either way, their off-screen relationship is clearly reflected in their on-screen bond.

Milo Ventimiglia and Penn Badgley

Penn Badgley had a pretty famous roommate during his time on Gossip girl. Gilmore Girl’s Milo Ventimiglia and Gossip Girl’s Penn Badgley shared an apartment. Despite being on separate shows, the two got along great. Milo was much older than Penn, which gave them almost a brotherly bond.

Penn Badgley on the red carpet / Milo Ventimiglia on the red carpet
Photo by Marion Curtis, StarPix, Shutterstock / Gregory Pace, Shutterstock

Penn spoke about the advantages of having an awesome roommate who happens to be ten years older. In 2011, the actor admitted to Bullett Magazine, “I used to borrow his ID to get into bars. I’ve still got it somewhere.” I would have loved to hang out at their place! It sounds like a fun apartment.

Brad Pitt and Jason Priestley

In 1987, way before getting their respective big breaks on 90210 and Thelma & Louise, Hollywood heartthrobs Brad Pitt and Jason Priestley moved into an apartment together. In his book, Jason Priestley: A Memoir, the TV star recalled some of his memories of his former roommate.

Jason Priestley at the Golden Globe awards in 1994 / Brad Pitt holding his Golden Globe award on the red carpet in 1996
Photo by Bei, Shutterstock / Bei, Shutterstock

“Just for fun, we used to have competitions over who would go the longest without showering and shaving,” he said. “Brad always won.” That must have been quite the bachelor pad. I mean, two hunks in the same apartment? I’m sure neither of them had problems with the ladies… even without a shave and shower.

Justin Long and Jonah Hill

Out of all the roommates on this list, this one is pretty random. When you think of Jonah Hill’s roommate, someone like Seth Rogan comes to mind. However, his roommate was none other than Justin Long. The actors lived together for a while but decided to part ways after bickering over minor issues such as recycling.

Jonah Hill and Justin Long on the red carpet in 2007
Photo by Alex Berliner / BEI / Shutterstock

“Jonah would recycle everything,” Long admitted on Watch What Happens Live. “We started getting in little fights – he left the bathroom door open, didn’t clean up after himself. Little things like that.” I can totally picture this situation, and it’s making me laugh. Everyone who has ever lived with roommates understands the struggle.

Lindsay Lohan and Raven Symonè

It doesn’t come as a surprise that these two former child stars crossed paths in Hollywood. Apparently, Lindsay Lohan and Raven Symone met at a photoshoot, and they decided it would be fun to rent an apartment together. And it was… at least for Lindsay. According to Raven, the living arrangement was pretty brief, and Lohan wasn’t around much while it lasted.

Lindsay Lohan on the red carpet in 2003 / Raven Symone on the red carpet in 2005
Photo by Picture Perfect, Shutterstock / Picture Perfect, Shutterstock

“She paid rent, and she was there probably three times,” Raven told US Weekly back in 2008. “She had her clothes in the apartment we were supposed to live in together.” Well, I’m sure I don’t need to remind you what Lindsay Lohan was up to in the early 2000s. But it makes sense that she wasn’t home much.

Adam Sandler and Judd Apatow

Judd Apatow and Adam Sandler are extremely famous faces now, but there was a time where both of them were relatively unknown. While they were struggling comedians in Los Angeles, the future stars were roommates in a San Fernando Valley apartment. As it turned out, the living arrangement was great!

Judd Apatow and Adam Sandler on the red carpet in 2009
Photo by Alex Berliner / BEI / Shutterstock

During a 60 Minutes Overtime segment, Sandler looked back at their time as roommates and said: “We were doing as comedians, good enough to get by. We could eat at Red Lobster once a month. That was a big night out.” I bet they never realized that one day they would be able to eat at Red Lobster every night.

Ryan Gosling and Justin Timberlake

Back in the ’90s, Ryan Gosling and Justin Timberlake starred on The Mickey Mouse Club, alongside future superstars Britney Spears and Christina Aguilera. The adorable kids were featured in skits together, but they also had a close off-screen relationship. When Gosling’s mom had to go back to Canada, Timberlake’s mom became his temporary guardian so that he could continue filming in Orlando.

Ryan Gosling on the red carpet in 2018 / Justin Timberlake holding his People Choice Awards in 2017
Source: Shutterstock / Photo by Jim Smeal, Shutterstock

“His mother had to keep her job in Canada that second year that we were on the television show,” Timberlake explained to Ellen DeGeneres. “We were probably a little closer than the rest of the kids that were on the show just because we had to share a bathroom.” Can you imagine if they were roommates as adults? That would have been the most epic apartment ever!

Kiefer Sutherland and Robert Downey Jr.

Robert Downey Jr. and Kiefer Sutherland lived in an apartment together for about three years in the ‘80s, before either of them landed their big breaks. The roomies grew to become close friends, and they were always there for one another. They loved living together, had a lot of fun, but also went through difficult times together.

Kiefer Sutherland on the red carpet / Robert Downey Jr on the red carpet
Photo by People Picture, Willi Schneider, Shutterstock / Lumeimages, Shutterstock

In 2016, Downey told Howard Stern that Sutherland “was a shoulder [to cry on]” for him, when he was dating girlfriend Sarah Jessica Parker, and their relationship hit a rocky point. Sure, that romance is history now, but, at the time, it was heartbreaking. They stuck together through thick and thin, so it’s no surprise that the ex-roommates are still friends.

Emma Stone and Bradley Cooper

It’s no secret that Bradley Cooper and Emma Stone know each other from the Hollywood circuit. But when they started working on the movie Aloha together, the two formed a close friendship. Cooper said, “I got to know her so well. When you spend four months with somebody, especially if you’re on location in an isolated area such as an island–”

Emma Stone and Bradley Cooper posing together
Source: Shutterstock

Emma interrupted, saying, “You’re forced to get to know them and hate them. You either hate them, or you know them, and then you hate them.” Well, when Cooper’s lease was up during filming, Stone asked him to move in and be her new roommate. Or, as Cooper puts it, “housemate.”

Christopher Reeve and Robin Williams

In the early ‘70s, before either of them had made a name for themselves, Robin Williams and Christopher Reeve were studying at the prestigious Julliard School of Drama in New York City. That’s right; the comedian and future Superman star were college roomies! Can you imagine how much fun that dorm room must have been? Reeve’s wife Dana referred the duo as “closer than brothers.”

Christopher Reeve and Robin Williams at an awards ceremony 1980
Photo by Fotos International / Shutterstock

Their strong brotherly bond continued after their college years and well into their Hollywood careers. Over the years, the two have always been there for each other – specifically, in 1995, when Reeve became a quadriplegic after an accident.

Conan O’Brien and Jeff Garlin

In the summer of 1988, way before either of them were successful, comedians Conan O’Brien and Jeff Garlin were roommates. And, let me tell you, they were just as funny then as they are now. They must have a ton of hilarious stories from living together, but O’Brian revealed one scenario where Garlin would kick open doors.

Jeff Garlin and Conan O’Brien on his late night show
Source: IMDb

“I’d be fast asleep, it would be 3 in the morning, he would kick my door open, kick my door open as and say, ‘It’s pudding pop time.’” O’Brien revealed on his show. If only I knew what pudding pop time is… either way, O’Brien has a lot of patience. If my roommate did that to me while I was sleeping, I would be so mad!

Winona Ryder and Gwyneth Paltrow

Winona Ryder and Gwyneth Paltrow were inseparable in the ‘90s. The two were seen together all over Hollywood and were known to be best friends. The aspiring actresses moved in together for a long time and even dated fellow Hollywood BFFs and roomies, Matt Damon and Ben Affleck.

Gwyneth Paltrow and Winona Ryder at an event together in 1996
Photo by Alex Oliveira / Shutterstock

Sadly, Ryder and Paltrow parted ways in 1998 after a rumored feud. Reportedly, Paltrow stumbled upon the script for Shakespeare in Love lying around the house and decided to audition for the part. Not only did she land the role, but she won an Oscar for her performance. Yikes! I could see how that might have caused a strain on their living situation.

James Corden and Dominic Cooper

Movie star Dominic Cooper and The Late Late Show host James Corden were flatmates back in London before they made it big in the United States. Yep, these two Brits lived together, and, apparently, the only piece of cutlery they owned was a spatula. To me, that sounds like a classic boy’s apartment.

James Corden and Dominic Cooper sitting at a dinner table at an event in 2009
Photo by Alan Davidson / Shutterstock

Cooper has since become known for his incredible acting career, and Corden is a beloved talk-show host known for his hilarious segments like the, oh so popular Carpool Karaoke. If you haven’t seen it, go watch it right now. It’s so funny! And, after all these years, I hope these guys have more dishes lying around.

Michael Douglas and Danny DeVito

Michael Douglas and Danny DeVito are both big names in the entertainment industry. They had a classic bromance from old school Hollywood. The two met back in the 1960s while attending the American Academy of Dramatic Arts, and, two years later, the aspiring actors got an apartment together in New York.

Michael Douglas and Danny DeVito posing together at an event
Photo by Globe Photos / mediapunch / Shutterstock

Even with all their fame and success, this celeb duo remained close throughout the years. Douglas confirmed this during an interview with The Talks. They even worked on multiple projects together, including three films: War of the Roses, Romancing the Stone, and Jewel of the Nile. It’s nice to see that these former roommates still share a strong bond, despite their celebrity status.

Before getting famous roommates and embarking on successful careers in Hollywood, these celebrities were teenagers. Do you ever wonder what your favorite celebrities were like in high school? These recognizable faces were jocks and cheerleaders before they were stars.