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.