7 Horrible Cross-Dressing Comedies That Might Be Worse Than ‘Jack & Jill’

Monday, November 7 by
This makes money. 

Our eyes and faces are set to melt a la The Ark of the Covenant this weekend, when the Adam Sandler-in-drag comedy Jack & Jill hits theaters. Don’t blame Sandler, though. It’s not his fault. He’s just reached that inevitable point in his career where he’s required to do drag. It’s nature. You can’t fight it. In fact, if my calculations are correct, he’ll soon play a goofy cyborg who wants to become real or a guy who accidentally becomes president despite his love of cheese steak sandwiches.

Point being, you can’t be upset with Adam Sandler over this. He’s only going with the flow. However, he should have looked at all those who failed before him before taking on such an aggressively sh*tty project. If only this list existed last year. I feel somewhat to blame.

At any rate, here are seven cross-dressing comedies that might be worse than Jack and Jill.

Sorority Boys

In an attempt to clear themselves of a crime they didn’t commit, college guys Dave, Adam, and Doofer disguise themselves as women. The plan is to infiltrate their former frat-house and recover a tape that proves their innocence. Then they will be allowed to throw a big party that will get them high paying jobs regardless of their intelligence.

Makes sense to me.

Sidenote: Hey, Barry Watson. Sup?

Juwanna Mann

Probably the most important cross-dressing basketball comedy from the year 2002, Juwanna Mann tells the tale of a disgraced professional basketball renegade who, when banned from the league, reinvents himself as a female basketball star. It would have been a million times better if it included a scene where Juwanna lumps up Don Imus.

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