Vintage Photos of Pop Culture Icons in Drag

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Cross-dressing, whether for pleasure or for mischief (or for plays or films), is no new phenomenon. Every little child experiments with putting on the opposite gender’s designated garb, all on-stage women in Elizabethan theatre were played by men, and many people of both sexes have dressed in drag for a variety of reasons, from personal to professional. So why should our pop culture icons be any different? Click through to join in our celebration of drag in all its forms, and see some of our favorite musicians, artists and writers (though by no means a complete selection — we couldn’t find any photos of J. Edgar Hoover) indulging in a little cross-dressing from as far back as 1910.

Virginia Woolf and her friends dressed as Abyssinian dignitaries (she’s the one on the far left), 1910.

Marcel Duchamp’s alter ego Rrose Sélavy, photographed by Man Ray, 1921.

Frida Kahlo in drag, with sisters Adriana and Christina and cousins Carmen and Carlos Verasa, photographed by Guillermo Kahlo, 1926.

Two shots of F. Scott Fitzgerald in 1916, the leftmost of which was published in The New York Times as a publicity photo for Princeton’s Triangle Club musical, “The Evil Eye!.” The Times called Fitz “the most beautiful” show girl in the whole production. [Image via]

Two of Andy Warhol’s famous self-portraits in drag, 1981.

Mick Jagger and Jerry Hall. Photographed by Philippe Morillon, 1978.

Another side of Mick Jagger, photographed by Anton Corbijn, 1996 (we know this one isn’t exactly vintage, but look how great it is).

The legendary Ed Wood in drag, from the bonus materials of Legend Films’ release of Plan Nine From Outer Space. Also see Johnny Depp’s interpretation.

Keith Richards, in an outtake from the photo shoot for the cover of Have You Seen Your Mother, Baby, Standing in the Shadow?. Photo by Jerrold Schatzberg, 1966.

Keith Moon, 1973. [Image via]

But of course. Queen in their “I Want to Break Free” garb, 1984.

We tried to resist any photos of actors playing roles, but this photo of Charlie Chaplin from 1914’s A Busy Day is just too good. [Image via]