Crossdressing is a tradition in film stretching back into the silent era. No matter how the culture changes, there will probably always be something a little bit funny about a man in a dress. Women dressed as men are pretty funny, too, although somehow less so. Anyway, here are six movie crossdressers for you to peruse and enjoy.
Fatty Arbuckle. One of the originators of the classic gag, Roscoe "Fatty" Arbuckle was known for doing a particularly convincing imitation of a curvy and enthusiastic woman, both in his movies and on the stage. One famous story has Roscoe, as a child during the vaudeville days, taking the place of a sick female performer and doing such a good job that the audience couldn't tell the difference.
Ed Wood. Commonly considered the "worst director ever," Ed Wood is known for his liberal use of stock footage, amateurish actors, and cheap sets. He's also known for his love of Angora sweaters, as chronicled in his autobiographical film "Glen or Glenda". Ed Plays the titular Glen/Glenda, an L.A. transvestite just trying to make it in the world. Worth noting is that his story is narrated by Bela Lugosi.
Tony Curtis and Jack Lemmon. The two stars of the most famous crossdressing movie ever made, "Some Like It Hot", play characters who don't dress like women for fun; they do it because their lives depend on it. They're musicians, you see, and they have to go incognito as part of an all-female traveling band in order to escape the mob. They must do an okay job of it, too, considering they both end up with their fair share of gentlemen suitors.
John Lithgow. In Brian De Palma's psycho-thriller "Raising Cain", John Lithgow plays Cain, who suffers from multiple personality disorder. One of his personalities is Margo, who wears a red dress and basically looks just like a 50s suburban housewife-only she's probably a murderer, too (the rest of his personalities seem to have no compunction about killing). Her appearance in the final shot of the movie is one of the great shocks in movie history.
Greta Garbo. You might not think one of the most famous Hollywood beauties would make a convincing male, but she does a respectable job in "Queen Christina", in which she plays the Queen of Sweden who masquerades as a man to travel undetected. Respectable enough to fool John Gilbert, anyway, and that guy had a nose for sniffing out sausages.* (*Note: this is a ridiculous rumor with no basis in fact.)
Robin Williams. What better reason to throw on a dress and a high speaking voice than to reconnect with the kids you lost in a divorce? That is the gist of the plot of "Mrs. Doubtfire", in which Robin Williams does just that. We should also give props to the character of Mrs. Featherbottom, inspired by the Williams film and played by David Cross on "Arrested Development", though.