Who Is America's Most Beloved Cross-Dressing Male Movie Star?

7. Jack Lemmon & Tony Curtis, Some Like it Hot ($25M)

Billy Wilder's 1959 hit about two musicians who hide out from the mob in drag (clearly, mobsters are the dumbest villains in movie history) not only tipped the box office at $25M, it also won an Oscar and earned five additional nominations including Best Director, Best Screenplay, and Best Actor.

6. Shawn and Marlon Wayans, White Chicks ($70M)

Sometimes men in dresses work better in pairs than alone (see: Some Like It Hot). Other times, twice the cross-dressing means twice the freak-out factor, as in the Wayans bros. comedy White Chicks. Granted, the terror owed more to the whiteface than what Shawn and Marlon were wearing as two African-American FBI agents/brothers who go undercover as, well, blond Caucasian women. Despite the frightening prosthetic work and White Chicks' five Razzie awards, it debuted at #2 with a $19M opening weekend and went on to make over $113 worldwide. A sequel is reportedly in the works, so consider yourself warned.

5. Tyler Perry, Tyler Perry's Madea Goes to Jail ($90M)

The grand dame of modern male cross-dressing in the movies is, hands down, Madea -- or rather, her portrayer and creator, multi-hyphenate Tyler Perry. Taken as a whole, Perry's theatrically-released cinematic filmography has raked in over $519M worldwide in ten feature films, though the character of the feisty matriarch Madea, played by Perry in disguise, has only shown up in five of those films. And of those five Madea films, Madea Goes to Jail -- the popular character's most prominent starring vehicle -- earned the biggest box office at $90M. Can her next outing, April's Madea's Big Happy Family, top her biggest performance to date?

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