What A Drag: The 5 Best Moments of Girls Dressed Like Dudes in Movies

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There’s a lot of controversy surrounding a new show on ABC called Work It, about two men who dress as women to get jobs (as if it was that easy!) But let’s face it, dressing in drag has been a part of entertainment, since like, forever, and shows no signs of slowing down. Dylan and Cole Sprouse did it on Suite Life, Victoria Justice did it on Zoey 101 and without it there would be no classic moments with Lady Gaga as Jo Calderone on MTV or James Franco at the Oscars (pink was definitely not his color!).

Some of our favorite teens have taken part in playing Mr. & Mrs. dress up for the big screen. And whether it’s a disguise or another case of mistaken identity, dressing as the opposite sex has brought us some of the best laughs. Here are some goodies:

She’s the Man
Amanda Bynes did it so should could play soccer in the teen take of Shakespeare’s Twelfth Night.
The old adage “If you can’t beat ‘em, join ‘em” definitely took on a little extra meaning here.

Sorority Boys
Three typical frat guys dress as sorority girls when they need to find a place to live and they end up finding out who they really are. Pretty deep stuff for a comedy starring guys in dresses.

Just One of the Guys
In this 1985 flick, Terry thought she was being discriminated against because she was a girl. So of course the only way to prove it was to dress up as a guy. Duh! Sounds like the perfect plan to me.

Pirates of the Caribbean: Dead Man’s Chest
Keira Knightley’s Elizabeth Swann disguises herself as a cabin boy in this flick. And I’m pretty sure she’s the best looking cabin boy any of those pirates ever laid their eyes on.

Shakespeare in Love
Viola becomes Thomas Kent for love… her love of the written word. In order to perform in a play by a young William Shakespeare, she binds her boobs and dresses as a boy. This role got Gwyneth Paltrow the Oscar, BTW, and we think it’s pretty obvs why.

So, what’s your absolute fave gender-bending movie moment? Think you’ll tune into Work It? I wanna now right here!

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