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.

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.

Shaq will be making a cameo as himself in Adam Sandler’s new film Jack & Jill. The recently-aquired Boston Celtics center is no stranger to playing Shaq in films. In fact, I imagine he prefers it to a genie on Iron Man rip-off superhero. Shaq has played Shaq in CB4, Good Burger, He Got Game, After the Sunset, The Kid & I, The House Bunny, and When in Rome. No one captures the essence of Shaq like Shaq can, which is why Sandler came to him for the Shaq role in his new comedy.

Regarding the film, Adam Sandler plays twins and one of them is a girl. Do I really need to go into anymore detail or have your eyes permanently rolled into the back of your skull? Shaq joins Katie Holmes and Al Pacino, who have already agreed to take a check for appearing in this inevitable sh*t sandwich. And don’t get all pissed at me about Sandler. I used to love the guy in Happy Gilmore and Billy Madison, but Grown Ups really took a toll on my emotional psyche. Never have I wanted an actor to devolve so badly and return to speaking gibberish. (TheWrap)