You may not think of yourself as a big fan of cross-dressing movies, but I'll wager you laugh hard at Jack Lemmon, Tony Curtis, Dustin Hoffman, Johnny Depp and Robin Williams mincing about in women's clothing. Those guys are the stars of the most famous and widely popular comedies that gain laughs at least partly from the image of a dude who looks like a lady. Now that you know you are a bigger fan of this genre than you thought, it's time to dig a little deeper. Explore your masculinity or femininity or mascuninity or whatever by taking a chance on cross-dressing comedies that aren't safely mainstreamed.
"Kinky Boots" is part dramatic cross-dressing film and part comedic cross-dressing movie. Let's say it's about 60-40 weighted on the side of comedy. What could be funnier than a big black guy dressing up in women's clothing and wearing striking stiletto-heeled boots that zip almost all the way up to his hip? Well, how about a white guy being forced to wear those boots at a big Milan fashion show because he was a briefly a jerk to the much more fashionably conscious black transvestite? "Kinky Boots" doesn't bring on the big laughs that those movies with Tony Curtis and Johnny Depp do, but you just might learn a lesson along the way. Hopefully not, but there is the chance.
I cannot recommend that anyone actually watch "White Chicks" because that would be condoning torture. But then I realized that some people get pleasure from the very same actions wrought upon their body that most would consider torture. I'm not suggesting that watching "White Chicks" should be included on the list of actions considered torture by Amnesty International or that screenings of the film should be mandatory at every BDSM club in the country, but I wouldn't argue against such decisions, either. The problem is not that the two Wayans Brothers the Lesser are particularly less believable as women than Robin Williams. The problem is that title your cross-dressing movie "White Chicks" and peopling it with male black actors requires two hurdles to be overcome. That second hurdle was simply too great an obstruction to allow this transvestite comedy to be enjoyed in any other manner than that in which you enjoy the sight of Tim Curry in garter belt and stockings.
Within the Venn diagram that includes those who have never seen "White Chicks" is an ever-decreasing number of people who have seen the granddaddy of all cross-dressing movies from Hollywood, "Charley's Aunt." Within that same conceptual representation is probably a roughly equal number of people who have never seen "Charley's Aunt" but who have seen "White Chicks." You are likely to find a much larger percentage of the population who can be considered actual cross-dressers at least tangentially than the percentage represented by those who have crossed over from enjoying "White Chicks" to enjoying "Charley's Aunt." The latter may well be the first cross-dressing comedy ever made; a 1911 silent film made in Italy. Over the next half century the tale of a uncle persuaded to don women's clothing and masquerade as their aunt would reach the screen in one form or another at least a dozen times.
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