Top 10 Cross-Dressing Characters
Not that I'm an expert in this area. Really.
10. Hedwig and the Angry Inch (2001) - John Cameron Mitchell
I haven't actually seen this movie (I didn't even stay at a Holiday Inn Express last night) so I can't really write about it. But no self-respecting lister can create a list of only nine, and I can only think of nine others. And I hear this one was good. I'll put it in my Blockbuster.com queue and get back to you later.
9. To Wong Fu, Thanks for Everything, Julie Newmar (1995) - Wesley Snipes, Patrick Swayze, and John Leguizamo
These guys made cross-dressing cool again. What could be better than an ethnically diverse trio of hunky guys running around the desert—in dresses and makeup? I wonder how they pitched this one to the studio.
8. Ace Ventura: Pet Detective (1994) - Sean Young
Ok, not technically cross-dressing since she had been... how do we say it... altered. But Sean Young was believable as a man, don't you think? Besides the "discovery" scene (which virtually all of these movies have) parodies our #1.
7. Romeo + Juliet (199^) - Harold Perrineau (Mercutio)
Baz Luhrmann is a nut. Turning Shakespeare's beloved poet / philosopher into a drug dealing disco drag queen was a stroke of evil genius.
6. Shakespeare in Love (1998) - Gwyneth Paltrow
If this film had been done in Shakespeare's time, Gwyneth's character would have been played by a boy. That means we would have had a boy playing a woman playing a boy playing a woman. Cross-dressing chaos.
5. Mulan (1998)
I include this simply because it amuses me that Disney has an entry in this category.
4. Victor / Victoria (1982) - Julie Andrews
Virtually all I remember is James Garner, about to lay a wet one on Julie Andrews, proclaiming, "I don't care if you ARE a man." Oddly, that line seemed to work on Julie. I mean, it's a nice sentiment I suppose, but hardly a compliment. "Honey, I don't care if you DO have a hairy chest and a . . . well, you know. I'm going to kiss you anyway." Try that on your next date.
3. Tootsie (1982) - Dustin Hoffman
In which we learn that in order to understand women, you've got to BECOME a woman. Aren't we glad that idea didn't catch on? I learned everything I needed to know about women by reading Amy Tan novels. Come to think of it, maybe it would have been better to do it Dustin's way.
2. Some Like It Hot (1959) - Jack Lemon and Tony Curtis
For those who look down on cross-dressing, this film demonstrates that you can escape from the mob AND share a locker room with Marilyn Monroe.
1. The Crying Game (1992) - Jaye Davidman
Oh relax, I didn't spoil anything. It's been 13 years . . . how long do we have to keep this secret?!
Posted by Bill Stevenson at May 2, 2006 4:16 PM
Comments
Bill, I'd like to add Eddie Izzard's stand up routine "Dressed to Kill" to your list. Foul and very funny.
Posted by: Gayle Thomas at June 12, 2005 5:37 PM
Seems I missed a few others too... I've been reminded of Boys Don't Cry (Hilary Swank). Didn't see it.
But the most glaring omission is the countless Monty Python characters played by men in dresses. In fact I could probably make another list of JUST those characters, in which case I'd have to rename THIS list "Top Ten Cross-Dressing Characters That Were Not in Monty Python Movies."
Posted by: Bill S at June 12, 2005 10:33 PM
Very nice Bill. I was glad to see you had Tony Curtis and Jack Lemmon as number 2 since I knew who your number one would be before I even started reading the list. Also does the cross-dresser in - Midnight in the Garden of Good and Evil - count? Because he was playing a cross dresser based on a character in a book that was based on him in real life???
I really liked the Fight Club piece as well and am looking forward to the second installment.
Posted by: Beth at June 14, 2005 4:24 PM
I was especially glad to see your 5, 6, and 7. Luhrmann's Mercutio arguably stole the movie, playing him as a little in love with his best friend, up against an almost nearly-as-strong Tybalt. I've actually found Mulan to be equally amusing and disturbing when considering the cross-dressing and gender implications, taking into account the songs sung about men and women's roles, Mulan's actions, her friends in the Chinese army and how they behave ... I know, I know, it's a cartoon, but sometimes I wonder just how much Disney realizes what it's doing in its attempt to be PC or whatever.
But where, oh where, is Farewell, My Concubine? Especially since -- correct me if I'm wrong on this -- the actor playing the concubine figure in this movie made a career out of this particular type of role and recently killed himself in a way similar to one of his other cross-dressing characters ....
Posted by: Shelley Wunder-Smith at June 15, 2005 1:24 AM
The new Pride and Prejudice was horrible, terrible, awful, and it was even worse with that Keira Knightly Cool Girl!!!!!!!!!!!!!!!!!!
Posted by: Faustina at February 10, 2007 3:07 PM