Surprising Celebrity Drinking Buddies
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While we’d relish the opportunity to grab a cocktail with a star Hollywood actor, sometimes, after a long day, all we want is a stiff drink and the company of a good friend. And that got us thinking: Who do celebrities truly like to imbibe with?

Sure, there are plenty of well-known friendships, like 2013 Golden Globe hosts Tina Fey and Amy Poehler, but we found a few who made us do a double-take. From a pair of rival pop princesses to a legendary country star who’s best buds with an Oscar-nominated actor, here are seven sets of famous friends who like to hit the town.

Which pair surprised you the most? Tell us in the comments below!

Rihanna & Katy Perry

Pop princesses Rihanna and Katy Perry have had their fair share of ups and downs (don’t even get us started on John Mayer—or Chris Brown), but surprisingly, they aren’t the frenemies you might imagine. The two have been best buds since 2009 and are often spotted out on the town, Instagraming photos of their antics. But what do the ladies like to drink? While Riri is admittedly a fan of Jameson, Perry seems to be less loyal to a single brand. 

Robert Pattinson, Vince Vaughn & Joaquin Phoenix

On the spectrum of unexpected celebrity pals, this trio ranks pretty high, if not only for the fairly wide age gap. Earlier this year, the three amigos were spotted out together in LA while, we imagine, throwing back drinks and getting into some seriously odd conversations. 

Leonardo DiCaprio & Tobey Maguire

This duo’s friendship isn’t limited to just on-screen imbibing in The Great Gatsby (although we hope they drink Prohibition-era cocktails like the Orange Blossom and Gin Rickey in real life, too). The bromance between Leonardo DiCaprio and Tobey Maguire has supposedly been going on for more than 20 years, since the two both auditioned for a role on the early-‘90s sitcom Parenthood.

(Photo courtesy Warner Bros. Pictures)

Charlie Sheen & Antonio Villaraigosa

Former mayor of Los Angeles Antonio Villaraigosa may not recall this particular wild night out, but Charlie Sheen was more than happy to give details of their supposedly “memorable” time partying together in Cabo earlier this year. According to the actor, it involved lots of women and booze at his suite’s bar in the Hotel El Ganzo. While the evidence may be suspect at best, this is definitely one of the most surprising pairs we’ve ever heard of—even it is just a figment of Sheen’s vivid imagination.

(Photo via Twitter/@charliesheen)

Jay-Z & Kanye West

Perhaps it’s not so surprising that these two rap greats would grab a drink every now and then; they did work on an album together. But knowing how ambitious both stars are, with ‘ye designing a clothing line and Jay starting a sports management agency on the side, it’s hard to think of them just kicking back and enjoying some Champagne or cognac.

Woody Harrelson & Willie Nelson

Woody Harrelson may have gotten his start as the dim-witted bartender on Cheers, but the Oscar-nominated actor has gone from hanging out with bar flies to drinking with legendary country star Willie Nelson. The pair even co-hosted a Texas hold ‘em tournament for charity.

George Clooney & Cindy Crawford

It’s not what you think. George Clooney is good friends with former rock-star bar owner Rande Gerber, and the two even created Casamigos Tequila together. (They were spending a lot of time down in Mexico supervising the construction of their vacation homes when they decided to start their own brand.) So what does this have to do with super model Cindy Crawford? Well, she’s married to Gerber, and they all hang out together often.

(Photo courtesy Casamigos Tequila)

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  1. Leonardo DiCaprio & Tobey Maguire

  2. This is an a poor list. Lots of rich people, but a poor list nonetheless.

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