"You're just a boy in a dress..."

It is a time honoured fashion in Hollywood for famous male leads to take parts in which they dress in drag. In the past is has been alternately touching, funny, conversational and just plain fun. So when I found out that Ryan Reynolds is being tapped to don women's clothing in order to "win back his ex-girlfriend by befriending her" it got me thinking (and not just about how bad I think this film will be).

There have been many quality films working with this as their premise. I have put together a must-see list of gender bending film forays that I think everyone will enjoy. Each has a different aim or message but ultimately they all take a moment to make us examine ourselves (as any good film should).

So enjoy!


To Wong-Foo Thanks for everything, Julie Newmar (1995)
After Vida Boheme and Noxeema Jackson win a major New York drag contest and a trip to Hollywood, they are persuaded to take the inexperienced drag princess Chi-Chi with them. They hire a beat-up old Cadillac and set off for Los Angeles, but their car breaks down in a small town in the middle of nowhere. With just their wits and an endless supply of garish costumes, they transform the town and everyone who lives there--until homophobic cop Sheriff Dollard catches up with them...

Tootsie (1982)
Michael Dorsey is desperate; he can't find a job. That is, until he gets a female role in a soap opera and becomes very famous. Of course, nobody knows that this new television star is a man... But, after a while, he falls in love with the leading actress of the series, and here is the big problem: how can he express his feelings, since she thinks that Michael is a woman?

Some Like it Hot (1959)
Two struggling musicians (Tony Curtis and Jack Lemon) witness the St. Valentine's Day Massacre and try to find a way out of the city before they are found and killed by the mob. The only job that will pay their way is an all girl band so the two dress up as women. In addition to hiding, each has his own problems; One falls for another band member but can't tell her his gender, and the other has a rich suitor who will not take "No," for an answer.

...That's all for now but feel free to post your own suggestions!