Wait, they roomed together? Surprising celeb duos who once lived together

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What if your roommate was a future Oscar winner? You would probably think twice about pissing them off with passive-aggressive notes, obviously!

Long before they were stars, and before the multi-million dollar paychecks and enormous homes, some of today’s hottest celebrities lived a lot like us. Life as a struggling actor meant having to split the rent for a tiny apartment. And who better to run lines with than another aspiring star?

In light of awards season, which kicked off last week in Hollywood, we’ve rounded up a list of 10 celeb duos who were roommates. Some of these roomies you may have heard of before, like Matt Damon and Ben Affleck, or Ryan Gosling and Justin Timberlake, but what are the odds both roomies go on to become uber famous? It happens more often than you think.

Although some roommates end up as mortal enemies or cautionary tales, both members of each of these celeb pairings achieved their dreams. Was it because of innate greatness or just the mutual desire to be successful enough to live alone? Whatever the reason, some of these famous flatmates even remain good friends to this day.

1) Jonah Hill and Justin Long 


Jonah Hill and Justin Long are two lovable leading men known for being a little bit awkward, very funny, and impossibly endearing.These comedy stars have been besties for a long time, but their time as roommates almost tore them apart when they were roommates in 2009.

Though still friends, Long said he finally moved out because he was constantly nagging Hill to pick up after himself, so they decided to save their friendship by getting their own places. They’ve since achieved enough success that they can have their own living spaces, where they’re free to live in whichever way suits them best.

2) Lea Michele and Dianna Agron


Back when Glee first started, leading lady Lea Michele (Rachel) and head cheerleader Dianna Agron (Quinn) were best of friends and they were roommates in 2009. That was until Dianna had to move out because she was allergic to Lea’s cats. Unfortunately, their friendship didn’t seem to survive either, and the two are no longer close.

3) Judd Apatow and Adam Sandler


Judd Apatow and Adam Sandler met when they were both young comics at the Hollywood Improv, and still completely unknown.

The pals shared a small apartment in the San Fernando Valley, and Apatow has said that living with Sandler was like living with “the comfortable naked guy at the gym.”

 4) Matt Damon and Ben Affleck


It is no secret that this duo grew up together in Boston and were childhood friends. They lived together while writing their hit film, “Good Will Hunting.” 

“We rented this house on the beach in Venice and 800 people came and stayed with us and got drunk,” Affleck once said.

Clearly now, these Oscar winners no longer need each other’s help to pay their rent.

5) Kiefer Sutherland and Robert Downey Jr.


Although both Kiefer Sutherland and Robert Downey Jr. had parents who were successful in the entertainment industry, they had to pay their dues like any other young actors. For three (presumably wild) years in the ’80s, the pair lived together in a Los Angeles apartment while trying to start their careers.

6) Jude Law and Ewan McGregor


Although they both hail from Great Britain, Jude Law (English) and Ewan McGregor (Scottish) didn’t meet until 1990 in Los Angeles. A director gave them $30 and told them to “get drunk to see what happened.”

They ended up moving in together, and eventually co-founded their own production company called Natural Nylon.

7) John Cusack and Jeremy Piven


John Cusack and Jeremy Piven may have been childhood friends, growing up together in Evanston, Ill., but living together in Chicago may have ruined their friendship.

When asked how Cusack handled his success, Piven said, “No comment. I mean, you could fill in the blank, I bet.”

8) Michael Douglas and Danny DeVito


A-listers, Michael Douglas and Danny Devito shared an apartment on New York’s W. 89th St. back in 1966, when they were both just starting out in the world of showbiz. Two years later they moved in together and are still friends today.

“Michael did the laundry,” DeVito once dished, while his old roomie claimed, “Danny was sloppy. No, really, he was a great roommate. It was a magical time. We were getting paid to act!”

 9) Chace Crawford and Ed Westwick


When Chace Crawford and Ed Westwick first landed their roles on CW’s “Gossip Girl,” they rented a New York City apartment together in 2007. These young bachelors lived together for about two years, until Crawford moved to a new place in the Financial District in 2009, partly because Westwick was a total slob…that would have been a juicy story for GG.

10) Ryan Gosling and Justin Timberlake


Justin Timberlake and Ryan Gosling lived together in the early 90s when they were pre-teens on The Mickey Mouse Club. Don’t worry — JT’s mom was there too. That didn’t stop the scamps from “stealing” a golf cart to joyride around the set lot though!

The next time you’re tempted to lecture your roommate about cleaning the bathroom or to argue about whose turn it is to do the dishes, imagine that person holding an Academy Award or millions of dollars. You never know who your roommates could turn out to be—so you’d better keep them on your good side.

Trouble splitting rent with your soon-to-be famous roommate? Check out Pay with Roommates on RadPad!

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