Actors, by their very definition, are chameleons. They take on personas that differ greatly from their own, and for that they are handsomely rewarded. But sometimes an actor takes on a role that's so far out of their reach that, no matter how talented they are, it simply doesn’t work.

This is usually the case when an actor attempts to play a member of the opposite sex. Whether it’s a comedic gag or a serious, Oscar-baiting assignment, Hollywood is filled with terrible examples of men in drag and women in jock straps. For every jewel of cross-dressing cinema, like Robin Williams in Ms. Doubtfire, Dustin Hoffman in Tootsie, or Cate Blanchett in I'm Not There, there are about 10 examples of the subgenre gone wrong.

Sometimes horrendous makeup and costumes ruin the roles, other times it's the performance itself that is to blame. Either way, the likelihood of success is always small whenever actors try to play the opposite sex. And to warn people of the pitfalls of these types of performances before they go see Adam Sandler pull double duty as both an obnoxious man and his boorish twin sister in his must-miss comedy Jack And Jill, we’re counting down The 10 Worst Cross-Dressing Performances In Movies.

Written by Jason Serafino (@Serafinoj1)

Tags: jack-and-jill, adam-sandler, wesley-snipes, marlon-wayans, shawn-wayans, john-travolta, arnold-schwarzenegger
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