Fierce From Every Side! The 15 Most Androgynous Celebrities

August 29, 2013  |  
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Celebrities have been gender bending long before B. Scott hit the scene. Some men look like women, some women look like men. And they all made it big while pushing gender boundaries. Check out 15 of the fiercest androgynous celebrities.


Prince is so fabulous it’s like he’s a man and a woman at the same time. What other man can make women throw their panties on the stage while wearing lace and stiletto heels?

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Michael Jackson

How does the joke go?: “Only in America can a man go from a poor black boy to a rich white woman.” Too soon?

David Bowie

Prince’s only competition for king of the androgynous pop gods was David Bowie.

Source: WENN

B. Scott

BET was so wrong for asking B. Scott to change at their awards show this summer. He had his hair done, his face beat and then they made him put on a suit and wing tips. We’re supposed to be getting better at embracing the LGBT community. We bet they wouldn’t have made Prince change…

Boy George

The Karma Chameleon made his name as the boy who dresses like a woman. And we love that even though the androgynous ’80s are over, Boy George is still repping for gender benders with his fabulous blue eye shadow.

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Grace Jones

Nobody is fiercer than Grace Jones. This Jamaican sister turned a modeling contract into a recording deal and an acting career. We don’t know what it is about her, but the world can’t seem to get enough. She’s 65 and still packing houses when she performs.

Annie Lennox

Annie Lennox and the Eurythmics topped the charts for decades. Annie is one of the most successful gender bending recording artists and the UK’s most successful female artist.

Milli Vanilli

We don’t know who’s better at gender bending: Milli or Vanilli. But we do know that neither one of them can sing.

Andrej Pejić

A lot of models are androgynous, but Andrej Pejić takes gender bending to a whole new level. He primarily models women’s clothes and looks better than most women doing it.


Whatever happened to Bahamadia? She’s one of our favorite female MCs. Her lyrics are butter-smooth and her voice is testosterone-deep.

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Carrot Top

Comedian Carrot Top has been going through some…interesting changes since his hey day in the 90s. And he looks more and more like a woman with each transformation.

Jaye Davidson

Remember actor Jaye Davidson from “The Crying Game”? He looks so much like a woman that he broke into the industry playing a transsexual. And that role made him the first black British actor to be nominated for an Academy Award.

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Jared Leto

Even with a beard, Jared Leto looks a lot like a woman.

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Tilda Swinton

Actress Tilda Swinton is so androgynous she almost looks out of this world. We’d love to see Tilda and Grace together in a photo shoot.

Terence Trent D’Arby

Remember “Wishing Well”? Unfortunately,Terence Trent D’Arby only had a couple of hits back in the day. We think he should have put his effort into modeling instead. His voice was OK, but we know women who’d kill for his look.

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