Flavorwire

There are some celebrity friendships that seem perfectly natural: Kanye and Jay-Z, Jon Stewart and Stephen Colbert, Hugh Laurie and Stephen Fry. And then there are the pairs who you’d never put in the same room — until they end up there, splitting a bottle of wine. That’s what happened with the Beastie Boys’ Mike D and Bright Lights, Big City author Jay McInerney at downtown Manhattan spot Acme last week, and they’re not alone. Apparently, celebrity makes for strange bedfellows; click through for photos of some of the most unlikely cross-genre pairings, from a country music queen and a famed street artist to two of the most powerful ladies in the entire world.

Dolly Parton and Keith Haring

Photo credit: Andy Warhol via Awesome People Hanging Out Together

Neal Stephenson, Neil Armstrong, and Neil Gaiman

Photo via Neil Gaiman’s Journal

Marcel Duchamp and John Cage, Toronto, 1968. Photo via Awesome People Hanging Out Together

Marilyn Monroe and Carl Sandburg

Photo credit: Len Stackler

RZA and Yoko Ono

Photo credit: Lester Cohen

Brad Pitt and Frank Gehry

Photo via Awesome People Hanging Out Together

Bear Grylls and Jake Gyllenhaal

Anthony Kiedis, David Bowie, and Johnny Depp

Photo via Awesome People Hanging Out Together

David Bowie and Elizabeth Taylor

Photo credit: Terry O’Neill

Pee-wee Herman and Cyndi Lauper

Carlos Santana and John McEnroe 

Photo credit: Lynn Goldsmith

Paul Simon and Lorne Michaels

Mr. T and Louis CK

RuPaul and Nirvana

Photo credit: Kevin Mazur via MTV

Betty White and Slash

Colonel Sanders and Alice Cooper

Jimmy Page and William S. Burroughs

Photo via Arthur Magazine

Meryl Streep and Hillary Clinton

Photo via BuzzFeed