9 Cross-Dressing Comedies That Are Probably Better Than Jack & Jill

Friday, November 11 by
Somehow, this is the second funniest film of all time. 

Earlier this week, as we attempted to find cross-dressing comedies that were probably worse than Adam Sandler’s Jack & Jill, we discovered there is a suprising amount of really great cross-dressing films. Looks like Sandler really has his work cut out for him if he wants to go down in history alongside these classics (listed below in no particular order). Otherwise, he’ll end up etched into history alongside White Chicks.

Ed Wood

Tim Burton‘s homage to the classically shitty director stars Johnny Depp in the title role. The film centers on Wood as he struggles to get his work made, be true to himself and his cross dressing, and his friendship with Bela Lugosi. I can only hope that twenty years from now, Tommy Wiseau‘s biopic is handled with the same class, wit, and decorum.

Just One of the Guys

What do you do when you lose the chance at a highly-coveted internship? Well, you automatically assume the world has it out for you because you’re so pretty and therefore disguise yourself as a member of the opposite sex and resubmit. What do you do when that doesn’t work? Assume the world has it out for you because your new Jo Calderone persona is so beloved, and disguise yourself in a gorilla outfit and resubmit.

Sidenote: Check out the picture above. Sucks to be Doris.

Shakespeare In Love

Way back in 1800 BC England, women weren’t allowed to act on the stage. The only way to do so was through the deceptive practice of disguising themselves unconvincingly as a man and strutting around with a sock in their pants. That’s exactly what Gwyneth Paltrow does in Shakespeare in Love. I think it’s also what Chris Colfer does on Glee.

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