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Drag In Hollywood Films: Which Actors Did It Best -- And Which Did It Worst?

First Posted: 11/15/11 09:34 AM ET   Updated: 11/15/11 11:04 AM ET

Eddie Murphy did it. The Wayan Brothers did it. Dustin Hoffman, too. So was anyone all that shocked when Adam Sandler decided to throw on a dress and give drag a spin for his new comedy "Jack and Jill"?

The film, which features Sandler playing himself and (in drag) his twin sister, was panned by critics -- the Washington Post said it was "borderline epic in its awfulness" -- but still managed to pull in $26 million during its first weekend in theaters.

Which raises the questions: Why does America get such a thrill from seeing their straight leading men in dresses? Is it offensive? Is it sexist? Is it funny -- and if so, when and why?

Below we've compiled a slideshow of famous leading men who've done drag on the big screen. Have a look, vote for the best and worst performances, and then let us know how you feel about the phenomenon -- and your favorites not featured below -- in the comments section.

'Jack And Jill,' 2011
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The film, currently in theaters, stars Al Pacino, Katie Holmes, and Adam Sandler who plays Jill, a character portrayed as overweight, lisping, annoying, socially inept and clumsy, and who gets punched in the face by a child to win laughs from the audience.
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Filed by Noah Michelson  |