Adam Sandler, Katie Holmes, Jack and Jill

Columbia Pictures

Jack and Jill, Adam Sandler's latest insult to moviegoers' intelligence, is a doozy, ranking among the all-time worst flicks on Rotten Tomatoes.

Happily, most films do not ask you to accept that the dude dressed like a lady is actually a let's-laugh-because-she's-ugly member of the fairer sex. But the sometimes-talented, sometimes-phoning-it-in funnyman is hardly the first actor to assume that dressing in drag equals laughs, no questions asked.

And as these five other films that prominently feature a cross-dressing character or two prove, if you don't have proper direction, capable actors or a decent script, all you've got is...

1. White Chicks: Perhaps the benchmark against which all other awful movies--regardless of low-brow concept--should be judged, this caper comedy starring Shawn and Marlon Wayans as cops who go undercover as, er, Caucasian women to bust...Oh, who cares what it was about?! Every second of it was unbearable, and Chris Rock touched more than a few nerves when, as host of the Oscars in 2005, he taped a bit about how mainstream moviegoers were lining up for crap like White Chicks instead of what was actually nominated for Best Picture.

2. Big Mommas: Like Father, Like Son: Yes, this sequel to Big Momma's House and BMH 2 was in theaters this year. No, we didn't see it, either. But someone thought people would watch Martin Lawrence put on the fat suit again—he wasn't about to let Tyler Perry's Madea steal all his thunder, was he?—and this time drag his onscreen stepson along for the gender-bending ride.

3. Yentl: Not Barbra Streisand's finest hour. While sometimes the iconic singer's filmmaking has paid off in more than soundtrack sales, this Streisand-directed flick about a bright young Polish woman who has to dress as a man if she wants to study with the other Jewish scholars at the yeshiva is more oy vey than anything else.

4. Juwanna Mann: Based on the title alone, this was a movie that could never, ever be given a positive review. Miguel A. Nuñez Jr.'s Jamal Jeffries has to go the women's basketball league route when his bad behavior gets him booted out of the NBA. Nuñez is lucky this movie didn't get him booted from Hollywood.

5. She's the Man: Now, if Amanda Bynes had said she was quitting acting right after making this, we would have understood. The Twelfth Night-inspired farce about a teenager who poses as her soccer-stud brother at boarding school is...well, it ain't Shakespeare. Come to think about it, perhaps borne of necessity since women weren't allowed onstage, the Bard really had cross-dressing as a meaningful plot device down.

With all this in mind, we recommend Some Like It Hot, Tootsie, Victor Victoria, Priscilla, Queen of the Desert, The Birdcage or, heck, even Mrs. Doubtfire to demonstrate how to do drag with purpose. And do be sure to tell us which heinous cross-dresing flick we left off our list!

GALLERY: Dude Looks Like a Lady

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