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

This Friday, Martin Lawrence's Big Momma's House franchise embarks on its third outing (Big Mommas: Like Father, Like Son) in an attempt to pass the gender-bending comedy torch to a new generation. The "men in dresses" subgenre, however, is nothing new. Why, fellas have been going undercover as ladies for years on the silver screen! (And, believe it or not, Tyler Perry is not the reigning box office king of cross-dressing comedy.) Hit the jump as we count-down the most bankable cross-dressing male movie stars of all time.

First, a few ground rules. We'll focus on films in which men don ladies' garb as disguise and not, say, dramas such as The Crying Game, female cross-dressing films like Just One of the Guys, or films like The Rocky Horror Picture Show or The Adventures of Priscilla, Queen of the Desert, which feature transgender/transsexual characters. (Tyler Perry's Madea character, though genetically female, is included on the basis of the transparency of Perry's performance.)

And so, without further ado, behold America's most beloved cross-dressing male stars, ranked in order of box office love:

10. Eric Idle & Robbie Coltrane, Nuns on the Run $10.9M

menindresses120.jpgThe "hiding out from the mob in the church" gag had been done elsewhere, and better (namely, a year earlier in We're No Angels) before this 1990 British nun-sploitation comedy starring Eric Idle and Robbie Coltrane notched a modest $10.9M North American box office showing.

9. Miguel A. Nunez, Juwanna Mann ($13M)

menindresses120.jpgA cocky male basketball player finds salvation -- and love, natch -- by masquerading as a WNBA hoopster in this terribly-received 2002 comedy. Portrayed by character actor Miguel A. Nunez (who made his bball comedy debut in Slam Dunk Ernest, though not in drag), Juwanna Mann taught audiences the ultimate lesson in basketball etiquette: go for the backboard-shattering slam dunk, and your showboating can cost you. (That is, if your wig flies off and the world realizes you're really a man.)

8. Jonathan Brandis, Ladybugs ($14M)


Similar stakes were at hand in this beloved 1992 kids sports flick, in which Rodney Dangerfield enlists his girlfriend's son (Jonathan Brandis, swoon) to dress like a girl to lead his soccer team to the championships. Paired with the Chuck Norris fantasy pic Sidekicks, Ladybugs made a teen idol out of young Brandis -- but it only stayed in theaters for three weeks.

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