10) Dustin Hoffman - Tootsie

We'll start with the obvious. Tootsie got Dustin Hoffman his fifth Oscar nomination, (You kiss Charles Durning and you may get one too) and a major case of razor rash, as he had to shave every three to four hours of shooting. Tootsie is one of the less attractive cross-dressers on our list, although 1 through 9 aren't exactly super models either, but he gets points for basing his performance on his mom, who passed away right before filming began.

9) Tony Curtis and Jack Lemon - Some Like it Hot

The golden oldie on the list. Curtis and Lemon play musicians who witness the St. Valentine's Day Massacre and hide in an all girl band. Brings up an interesting point, gender bender comedies often include hotties (Marilyn Monroe in this one) to add to the mayhem, and secure any chance of guys paying to see the flick.

8) John Cameron Mitchell - Hedwig and the Angry Inch

The story of an operation gone awry, a German-born singer named Hansel undergoes a sex-change operation to marry an American, but is left with an unfortunate "angry inch". She renames herself Hedwig and forms a rock band. In other words, your basic Hollywood love story. Started as an off-braodway musical...soon to be an xbox 360 game.

7) Prince Herbert - Monty Python and the Holy Grail

Man, the Monty Python boys sure did like to wear dresses, didn't they? At least they had the legs for it. I could have listed any of their classic movies...Brian's mom was a guy in Life of Brian. The catholic woman who pops out a puppy while she's doing the dishes in Meaning of Life was a dude, too. But I opted for Prince Herbert, who really wasn't even technically a cross-dresser, but he has his own action figure, and I did want a prince on the list.

And now for something completely different...

6) Divine - Pink Flamingos

Scorsese has DeNiro...Kevin Smith has that Jay guy...John Waters had Divine.

Waters and Divine (then known as Glen Milstead) met as boys in their hometown outside of Baltimore, Maryland. They formed an acting troupe called the DreamLanders, and the rest is history. Mr. Milstead starred in a slew of John Waters productions...Female Trouble, Polyester, Hairspray. But Pink Flamingos stands out as REALLY stretching the boundaries of good taste, for including a scene featuring Divine eating fresh dog feces. Sadly, Divine died in 1988 at the age of 43. Neither cross-dressing, nor feces consumption, have been the same since.

5) Linda Hunt - Year of Living Dangerously

And now...the only performer on our list who didn't require any makeup. (whoa, that's cold) Linda Hunt won an Oscar for portraying photographer Billy Kwan, covering a coup in Indonesia with reporter, Mel Gibson. OK, I'm not gonna lie to you all. I never saw this flick, and I never plan to. I just know Hunt played a guy...let's move on.

4) Julie Andrews - Victor Victoria

The story of a woman pretending to be a man pretending to be a woman, sort of a trans-trans-gender role. Victoria needs a gimmick to succeed as a cabaret performer, and decides to become a male impersonator, pretending to be a female impersonator. A classic example of cross gender storytelling. There's a hottie (Lesley-Anne Warren), lots of Oscar buzz (Nominations for Andrews, Warren and Robert Preston) and a classic reason given for the cross-gender transformation (a potential job opportunity)...text book gender bending.

3) Tim Curry - Rocky Horror Picture Show

Ok, this brings up another good point...gender benders flicks often have large cult followings, and Rocky Horror is the king of the cult classics. In it, Tim Curry plays cross-dressing Frank-N-Furter, a doctor who stretches the meaning of alternative lifestyle. Rocky Horror stands out, not only for its cult status, but as the only movie on the list that celebrates cross-dressing in song...I'm just a sweet transvestite. From Transexual, Transylvania

2) Hillary Swank - Boys Don't Cry

Say it with me...Hillary Swank is the new Meryl Streep, and she proved it from the very beginning by playing Brandon Teena, the popular new guy in a tiny Nebraska town, who was actually born a woman named Teena Brandon. Boys Don't Cry will always be number one when it comes to transgender Oscar talk, and it's forever doomed Hillary to being remembered as that goofy-looking guy, no matter how much she dolls herself up. (Sorry Chad)

1) Jaye Davidson - The Crying Game

The Crying Game was responsible for weeks of my thinking I needed therapy. (Shut up...kidding...I knew it was a guy all along.) I think this was the first time I ever saw a guy's package in a movie. (Now there's like one a week on this freaking blog)

If you've never seen it, it goes something like this....IRA foot soldier Fergus kidnaps British soldier, waits to hear whether he will execute his victim or set him free, and the two form a bond before Fergus eventually kills him. Later, Fergus unexpectedly becomes involved with the soldier's girlfriend Dil (Jaye) and discovers more than he ever expected (cue me falling out of my freakin' seat). The Crying Game...In my opinion, the number one gender bender flick of all time.

Honorable Mentions: Flawless, It's Pat, The Birdcage, Priscilla, Queen of the Desert, To Wong Foo, Yentl, Just One of the Guys.

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