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.

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.

But over the past few decades, something interesting has happened across the opposite gender lines: Opportunities for women to play men have grown increasingly varied and complex. Dating back to 1982's The Year of Living Dangerously, which earned Linda Hunt a Best Supporting Actress Oscar for playing the male Billy Kwan, women have regularly played men in dramas, with several examples (including Cate Blanchett's uncanny impression of Bob Dylan in I'm Not There) meriting critical claim and award-show recognition (2006's She's the Man—a teen comedy loosely based on Shakespeare's "Twelfth Night"—is one of the few exceptions).

It's no accident that this shift in female-to-male roles first occurred alongside the post-feminist boom of the 1980s. Significantly, the vast majority of films in which women play men are period pieces—depictions of the difficulties of womanhood in decades or centuries past. There's nothing amusing about the plight of Barbra Streisand's Yentl in Yentl: She disguises herself as a boy because it's the only way she can receive instruction in the Talmud. Gwyneth Paltrow's Oscar-winning performance in Shakespeare in Love was built around a character who disguises herself as a man to perform on the stage. Even Disney's Mulan has a life-or-death dilemma at the crux of its story: When Mulan's geriatric father is called, as the family's eldest male, to serve in the Chinese army, Mulan steps forward as her father's "son" to take his place.

But as female-to-male roles have embraced nuance and complexity, male-to-female roles have failed to evolve beyond the template set by Charlie Chaplin and Fatty Arbuckle. Recent years have seen both male-to-female cross-dressing plots, including Martin Lawrence's Big Momma's House trilogy, and male-to-female cross-casting, including Tyler Perry's six Madea films to date. But the cumulative effect of these movies is the same: When a man plays a woman, the implicit joke is his own emasculation. Even Billy Wilder's Some Like It Hot—arguably the funniest of the male-to-female cross-dressing comedies—mines most of its laughs from the emasculation of its protagonists. That less-laudable tradition is alive and well in Jack and Jill; Jill is so offensively, cartoonishly masculinized throughout the film that it's impossible to sympathize with her—let alone understand her as anything more than Sandler's ugly, sexist impression of a modern Jewish woman.

An actor with more skill or tact than Sandler may eventually step forward. But for now, male-to-female cross-casting still lacks a role on par with those offered by The Year of Living Dangerously or I'm Not There. And until contemporary Hollywood is willing to accept that there's more to masculinity than machismo, that's not likely to change.

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