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Celebrities who were once roommates

Raechal Leone Shewfelt
Editor, Yahoo Entertainment
Yahoo Style

Before they bought mansions in Beverly Hills or New York City penthouses overlooking Central Park, many celebs lived on a tight or nonexistent budget and often shared rent with someone in the same situation. Who knew they would both become famous?

Ryan Seacrest and Jensen Ackles

The talk-show host and the Supernatural star revealed on an episode of Live With Kelly and Ryan that they split the rent, before either was recognizable, and Seacrest even produced a photo. “You were on the radio,” Ackles said. “You were doing a morning show. I was doing a soap opera. We were the E-list. “Still, Seacrest teased, Ackles managed to get all the girls: “When you roll up to a party with him, no one wants to talk to me.” (Photo: Ryan Seacrest via Instagram)

Connie Britton and Lauren Graham

“We lived in an empty house that we weren’t supposed to be living in,” Graham confirmed on an episode of Watch What Happens Live. “We had no furniture and all we ate was Rice Krispies Treats.” Graham later revealed that Britton left the dishes in the sink “forever” and owned shoes that Graham liked to borrow on the sly. (Photo: Getty Images)

Kiefer Sutherland and Robert Downey Jr.

Downey “kind of” lived with both longtime girlfriend Sarah Jessica Parker and Sutherland for three years around the time the men co-starred in the 1988 movie 1969. Downey was dating Parker and — when they were having trouble, mostly because of his drug problem — Sutherland was around to console her. The Iron Man star told Howard Stern in May 2016, “He was a shoulder [for her to cry on]. Better him than some stranger.” (Photo: Getty Images)

Ryan Gosling and Justin Timberlake

While co-starring on The Mickey Mouse Club, the future heartthrobs were as close as brothers for a short time. “Funny enough, his mother had to keep her job in Canada the second year that we were on the television show and my mom was his guardian for like six months,” Timberlake told Ellen DeGeneres back in 2011. In fact, JT confessed the two once “stole a golf cart“! They’ve stayed friends, but the two are kinda busy these days. (Photo: Kevin Winter/Getty Images)

Penn Badgley and Milo Ventimiglia

While Badgley’s Gossip Girl co-stars Chace Crawford and Ed Westwick shared a space during the show, he lived with Ventimiglia, who happens to be a decade his senior. Of course, Badgley wanted to use Ventimiglia’s ID to get into the places that were off-limits to the then 18-year-old, and (of course) he said yes. (Photo: Getty Images)

Lindsay Lohan and Raven Symoné

Back in their Disney days, LiLo and Raven were all set to be roomies, but it didn’t quite work out that way. “She paid rent, and she was there probably three times,” Symoné explained to Us Weekly in 2008. “She had her clothes in the apartment we were supposed to live in together.” So she was a really good roommate! (Photo: Gregg DeGuire/WireImage)

Jude Law and Ewan McGregor

Sounds like American imports Law and McGregor had quite the time when they shared a residence in their pre-fame days, often hanging out with up-and-comers Angelina Jolie and her then-love Johnny Lee Miller in the U.K. “Jonny and Angelina were shooting Hackers, Jude had done Shopping. I’d done Shallow Grave,” McGregor told Nylon Guys for the February 2015 issue. “We were all kicking off. It was happening. We were having a right laugh. It’s the ’90s in London. It was quite fun… That’s all you’re getting.” (Photo: Getty Images)

Amy Smart and Ali Larter

The two met as models working in Italy and moved to L.A. to become actors. Soon both had roles in the 1999 teen classic Varsity Blues. (Photo: Michael Tran/FilmMagic)

Ben Affleck and Matt Damon

So, technically, Matt crashed at his childhood friend Ben’s couch when he first moved out to L.A., but surely that counts as at least an unofficial roommate. Ben, who was there because he had attended the local Occidental College, welcomed Matt and the unfinished script about a genius janitor that he brought with him. (Photo: Todd Williamson/Getty Images for Amazon)

Michael Douglas and Danny DeVito

It’s no coincidence that these guys worked together in several films, including the 1984 hit Romancing the Stone and 1989’s The War of the Roses. Douglas and DeVito roomed together, on West 89th Street in New York City, when both were taking acting classes. After a 2010 tribute to Douglas, New York magazine asked him about the kind of things they did together, to which Douglas replied, “Let’s just say, it was the ’60s.” (Photo by Allen Berezovsky/WireImage)

John Cusack and Jeremy Piven

The actors met while growing up in Chicago and shared the screen in many movies in which Cusack starred. (Remember Piven’s small role in “Say Anything…”?) They reportedly roomed together at one time — making them an earlier version of Matt and Ben –- but later had a public falling-out. (Photo: Gary Friedman/Los Angeles Times via Getty Images)

Tommy Lee Jones and Al Gore

In the ’60s, the Fugitive star and the future vice president of the United States shared an address while they were students at Harvard University. They became so close watching Star Trek and playing pool that, at the 2000 Democratic National Convention, Jones spokes favorably of Gore, calling him a “good, caring, loving man.” (Photo: Stephen Lovekin/WireImage)

Justin Long and Jonah Hill

Long was asked about the best and worst parts of living with the Superbad star back before they “made it big,” on an episode of Watch What Happens Live in 2016. “The best part,” Long answered, “was we laughed like hyenas. The worst was we were both equally pretty messy.” (Photo: Jason Merritt/FilmMagic)


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