Crossing Over: A History Of Black Comedians Dressing In Drag


Maybe Dave Chappelle wasn’t as crazy as we all thought he was. In a 2006 interview on Oprah, the former Chappelle's Show star, who'd fled from fame and fortune, theorized that Hollywood is trying to emasculate strong black funnymen by making them wear dresses. Despite writers, directors, and producers pressuring him to cross-dress, he took a stand and refused. Chappelle has been the exception, because when it comes to black comics, dressing up in drag is practically a right of passage.

Just look at Big Mommas: Like Father, Like Son, which opens this weekend (watch the trailer here). Star Martin Lawrence returns as an FBI agent who continually goes undercover disguised as a matronly old black woman. It's a re-hashed joke that stopped being funny five minutes into the franchise's first flim, Big Momma's House. There's really no purpose to this sequel—unless you consider that Lawrence's young co-star, Brandon T. Jackson, who plays his stepson, will be wearing women's clothes too. Two talented black comedians from different eras spending an hour and a half prancing around in drag: Baton officially passed. (How did we not include an entry for cross-dressing fuckery on our Black History Month Bingo card? FAIL!) We investigate this phenomenon by looking back at other instances of black comedians doing drag and what the justification was supposed to be. At least reading it won't be a drag.

7 Comments | Add a comment

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    Jerome Garfunkel February 18th, 2011 at 12:49 PM

    "we have never seen this Maya Angelou" are you serious complex. Was that a joke or just displaying ignorance. Smh during black history month as well. That comment was worst than this whole list.

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    flippin wat? February 18th, 2011 at 11:34 PM

    Chappelle was right.

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    Dookie Mercury February 20th, 2011 at 02:17 AM

    Sad still, the list does not count Arsenio Hall in Coming to America, Will Smith in Wild Wild West, or Chris Rock in an episode of "Fresh Prince"

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    The3Abyss February 20th, 2011 at 02:35 PM

    I didn't even read this article, but this topic has always bothered me. I find it sad. Now, I have no hate for actors/actress that do it, I guess you can say its there job to act as someone else, but I find it to be a sign weakness. Umm a last resort. I compare it to a relationship between a crack dealer and crackhead in times of desperation where the crackhead offers fellatio for some crack, due to lack of funds and the dealer thinking 'Well, I'll be getting a nut.' and so the deal is done.

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    branqon February 21st, 2011 at 10:12 AM

    you're forgetting an important one: tracy morgan as star jones on 30 rock, because he pointed out the whole "black men dressing in drag to appease whitey" trend and spoke against it, then decided to do it anyway because it's funny. another one is good burger. how can you skip good burger. smh.

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    shelly September 21st, 2011 at 06:38 PM

    off the topic of African American male comedians but Jack Lemon & Tony Curtis did it in 1956 Some like it Hot with Marilyn Monroe, Robin Williams, Rob Schneider etc. Is it comedians or just AA comedians that they try to minimize with this?

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      The Sonic Leroy October 20th, 2011 at 06:35 PM

      Don't forget that it still requires talent to be able to pull it off successfully. Either you can or you can't. At the end of the day, people in general need to lighten up. Life is too short to be worried about what gender someone else clothes or behavior belong to. Go find something to do besides point fingers. Up with individualism!

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