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I was having a discussion with a friend about Tyler Perry recently and they lamented that while they have respect for his achievements, it bothers them that he had to wear a dress to be a success. He went further to say that for Black actors, and specifically Black comedians, it is almost a requirement in Hollywood that at some point they dress up as a woman in order to advance. At first I was a little skeptical but when I did a little digging it seemed he had a point. From the late Flip Wilson to Martin Lawrence it’s a trend that you can’t ignore.

A few years ago Director John Singleton told Black Star News, “I’m tired of all these black men in dresses … How come nobody’s protesting that?” And comedian Dave Chappelle confessed to Oprah Winfrey that he’d been pressured to do drag. “I don’t need no dress to be funny,” he said. Chappelle also suggested that their insistence amounted to a “conspiracy.”

Another way to look at it is that it (ironically) takes a lot of balls to wear a dress on camera. Tyler Perry has countered in Essence that the criticism and speculation about his sexuality has, “given [him] a firm seating in [his] manhood.”

But what about womanhood? What message are we sending that when we decide to dress up like Black women that THIS is how we act? I’m not suggesting we toss our sense of humor out the window but if there were this many Black women dressing up as men and portraying us as loud, fat, or old we’d have something to say about it.

The whole thing didn’t sink in for me until I saw just how often it’s been taking place, so take a look at this gallery and weigh in on the topic: Does a Black man in Hollywood literally have to “dress” for success? Or is it no big deal?