Best Crossdressers

One of the best crossdressers of all time is Tim Curry in his role as the bizarre Dr. Frank N. Furter in The Rocky Horror Picture Show. The crossdressing extravaganza blazed a trail for dudes to get freaky in film. The sweet transvestite from Transexual, Transylvania may be more comfortable in ladies' underthings, but there's nothing feminine about Dr. Frank - he's an omnisexual predator who gets his jollies with whatever warm body he can find. Thankfully, his evil plans are foiled, but at what cost?

Most of the crossdressers on this list are satisfied with just a few items of clothing, but for Jame Gumb, the horrifying serial killer known as "Buffalo Bill" in The Silence Of The Lambs, that's not enough. Gumb wants to make a woman suit, and he wants to make it our of real women. To do so, he kidnaps them, keeps them in his basement, moisturizes their skin with the lotion in the basket, and then flays them. Pretty gross stuff, and the bit where he tucks it back and does his lady dance makes him one of the best crossdressers ever.

The merc with a mouth has never been one to let the rules of civilized society slow him down. So, when Deadpool was briefly inducted into the X-Men, he decided to get an old uniform out of storage - Jean Grey's. Needless to say, this didn't go over well with anybody. Especially since her original Marvel Girl duds showed a lot of skin, and Deadpool's skin is... how do we say this politely... completely repulsive. He claimed it was to give him a strategic advantage over his enemies, but I think he was just in it for the lulz.

In the classic Nintendo game Legend Of Zelda: The Ocarina Of Time, hero Link is aided in his quest by the mysterious Sheik, who guides Link to the hidden temples to awaken the sleeping sages and purge the land of Ganondorf's villainy. Sheik is a pretty ass-kicking dude, capable of a bunch of ninja tricks that Zelda can't pull off. She's also seen in two Smash Brothers games, and you can change from Zelda to Sheik at will.

Twin Peaks was chock full of quirky characters, so it's no surprise that was a crossdresser in the bunch. DEA agent Dennis Bryson comes to town to help Agent Cooper clear his name and investigate the drug ring at One Eyed Jack's, but Dennis has changed a little bit. On a case a few years back, Dennis needed to wear women's clothing to go undercover. He discovered that crossdressing relaxed him and has been doing it ever since. Played by David Duchovny, Denise (as he liked to be called) fit in just fine in Twin Peaks.

Sleaze classic, Beyond The Valley Of The Dolls, pulls out all the stops and the performance by John Lazar as the flick's villain is one of the best. As the psychopathic "Z-Man," Lazar chews scenery like a crazy person. His apotheosis comes when he puts on women's clothing and transforms into "Superwoman," his alter ego, who sets out to kill most of the cast. Z-Man takes things one step beyond the rest of this list, as he rips open his blouse to reveal a pair of surgically-added bazooms.

Adam Warren's Empowered comics are gleeful celebrations of sexual perversity, so it's no surprise that we'd see a crossdressing character. Guess what? He's awesome. The Maidman is a regular dude who has a deeply repressed personality that comes out when injustice rears its ugly head - and that personality loves to dress in a frilly French maid's uniform. That doesn't make the Maidman any less effective in the war against crime, however, as he's one of the most feared crime-fighters in the Empowered universe.

Neil Jordan's Breakfast On Pluto is a rich and robust tale of a dude who just loves to put on the clothes of a lady. Cillian Murphy plays Patrick "Kitten" Braden, a young Irish lad abandoned by his birth parents on the steps of a church. As he grows up, Patrick starts to embrace his inner freak, but the drugged-out lifestyle of the 1970s starts to drag him through the dirt. The flick is immensely touching and well worth watching, one of the best depictions of crossdressing ever.

It's important for a boy to love his mother, but things can go too far. Case in point: Norman Bates, the titular Psycho. Norman has a hard time letting go of his mommy, even though she's long dead, and he carries on long conversations with her. Things get even worse when we find out that Norman has a repressed personality that likes dressing up in his mom's old clothes and stabbing chicks to death in the shower. When we see Norman in full drag, it's quite the shock.

The Guilty Gear series of fighting games boasts a bevy of ludicrous characters, so it's no surprise that there's a crossdresser among the ranks. Bridget was born in a quaint English village where twins of the same gender were considered bad luck, so after a coin flip he was raised as a girl and made to join a nunnery. This kind of screwed with his brain, so he decided to prove that he was macho by becoming a bounty hunter. While still dressed in his nun's habit and skirt, of course.