Jack & Jill & Yentl: Hollywood's Cross-Dressing Double Standard

Adam Sandler's new Jack and Jill is the latest example of a cinematic cliche: When a man plays a woman, it's funny. When a woman plays a man, it's drama. Why?

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If you're looking for smart, nuanced depictions of gender in cinema, an Adam Sandler film probably isn't the best place to start. But for anyone who's curious to see Sandler's grating shtick applied to contemporary womanhood, Hollywood is giving you the chance. It isn't pretty.

Jack and Jill, which arrives in theaters today, stars Adam Sandler as both the titular Jack and the titular Jill. Jack is put-upon and insufferably smug, and Jill is a shrill, offensive Jewish caricature (and a contender for the most irritating cinematic character of the year, if not the decade)—but they both have Sandler's trademark charisma-less spirit. Cross-casting—that is, casting an actor in a role of their opposite gender—has long been one of Hollywood's favorite tricks. But Jack and Jill manages to be both a terrible cross-casting film and a terrible cross-dressing film, when (spoiler alert, for those who prefer their Adam Sandler comedies unsullied) Jack is forced to disguise himself as Jill in order to seduce Al Pacino.

Terrible as it is, Jack and Jill is a representative example of a long-standing trope: men playing women in slapstick comedies. It also stands, somewhat improbably, as an intriguing counterpoint to next month's drama Albert Nobbs, which stars Glenn Close as a woman who cross-dresses as a butler in order to survive in 19th-century Ireland. Taken as a whole, these two disparate films are emblematic of a consistent Hollywood trend: When a man plays a woman, it's for comedy. And when a woman plays a man, it's for drama.

As an acting tradition, cross-casting goes all the way back to ancient Greek theater, with parallel examples in Japanese kabuki and eventually in the English renaissance theater. In each of those eras, cross-casting served the same essential function: Women were not permitted to act on stage, so males (and usually young boys) played the female roles. We are, of course, happily past the sexist casting of those eras, and plenty of women now play dramatic and comedic roles on both stage and screen.

The vast majority of films in which women play men depict the difficulties of womanhood in decades past

But cross-casting never went away. It simply evolved into something different. The comic lineage of cross-casting in cinema extends all the way back to 1914, when Charlie Chaplin played a woman in the slapstick short A Busy Day. Cross-dressing came just three years later, in a series of shorts starring the legendary Fatty Arbuckle. Arbuckle classics likeThe Butcher Boy or Coney Island follow the same rough arc: Some contrived event—say, a crush in an all-girls' school—forces Arbuckle to disguise himself as a woman. If that sounds familiar, you're probably thinking of Tootsie, or Bosom Buddies, or Mrs. Doubtfire, or one of the countless other variations on this scenario throughout film and television history.

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Scott Meslow is entertainment editor at TheWeek.com.

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