Lady Gaga has made headlines once again, this time for the cover are of her new single, You And I (pictures one and two), in which she appears styled as a man (striking an uncanny resemblance, we at Stylist think, of Prince, Bob Dylan and Shane MacGowan in equal measures).

It's not Gaga's first foray into cross-dressing as a man – she first appeared in drag in Japan's Vogue Hommes (pictures three and four) - and she’s by no means the first star to step into the shoes of the opposite sex, as these photos show…

Annie Lennox

In 1984 Annie Lennox performed at the Grammy Awards dressed in drag. She explains, "There had been quite a controversy about my gender and so just to really push the envelope I took it on myself to shake them up a bit. I got a man's suit and I had makeup stubble. When I got to the stage to perform, the stage manager was totally freaked out because he couldn't see me. He didn't realize who I was. When the curtain came up, you could almost hear the audience inhale."

Gael Garcia Bernal

Actor Gael Garcia Bernal starred in Pedro Almodovar’s 2004 film Bad Education as Ángel Andrade, an actor who plays a drag artist and transsexual called Zahara in the film within the film.

Hilary Swank

Actress Swank played Brandon Teena in the 1999 film Boys Don’t Cry which told the real life story of Teena, a transgender man who was raped and murdered by his male acquaintances after they discovered he was biologically female. She won a Best Actress Oscar for her performance, and spent a month living as a man so convincingly that neighbours believed her brother was visiting.

James Franco

We like a man who isn’t afraid to drag up from time to time, and James Franco proved he’s up for the challenge when he was photographed by Terry Richardson in full make-up and women’s clothes for Candy magazine – a “transversal style magazine”.

Sharleen Spiteri

The frontwoman dressed up as Elvis (complete with sideburns) in the video for Texas’ 2000 hit, Inner Smile.

Marc Jacobs

Designer Jacobs was styled by Katie Grand in pieces from her wardrobe (that he designed) for Industrie magazine. Sans beard, we think he’d make quite a pretty lady – just look at those dainty ankles…

Cate Blanchett

The actress was the only female actor chosen to play Bob Dylan in the ensemble cast of I’m Not There, the 2007 biographical film inspired by the legendary singer-songwriter. With her beatnik shades and tousled tresses, Cate manages to look convincing both as Bob and in her own right.

Image credits: Rex Features, Nick Knight for Vogue Hommes, Terry Richardson for Candy, Patrick Demarchelier for Industrie