Katt Williams’ multiverse-shattering Jan. 3 “Club Shay Shay” podcast interview has beget more threads of discussion than most folks can keep up with. Among them is the revived discourse around famous Black men in dresses.
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Williams made the outrageous claim that he placed in his contract that he’d only act with Rickey Smiley again if Smiley wore a dress. He also expressed disappointment that Martin Lawrence wanted Williams as his sidekick wearing “his first dress” in 2011’s “Big Momma’s House: Like Father, Like Son.” He claimed that he turned it down, suggesting Brandon T. Jackson for the role.
It’s a conversation we’ve had ad nauseam for years now: Many Black people are convinced that a Black man donning drag to entertain (white) folks is problematic on its face. The pilot of the short-lived, underrated 2017 Jay Pharoah Showtime comedy “White Famous” guest-starred Jamie Foxx to lampoon the issue of Black comedians needing to wear a dress to take off.
Dave Chappelle told Oprah Winfrey as a guest on her show in 2006 that he was skeptical of Black men wearing dresses in film and refused to do so.
Even academics have suggested it’s a problem: University of Southern California Critical Studies Professor Todd Boyd has been openly critical of Black entertainers in dresses. The roles “humiliate and emasculate black men — it renders them less than powerful,” Boyd told the Chicago Tribune in 2017.
I side with comedian Marlon Wayans – who donned a dress for the 2004 cult classic “White Chicks” – on the issue: During a recent appearance on The Cruz Show, he said the conversation around Black men in dresses is a ridiculous one to have in 2024.
“You talking to a Black man that put on a dress,” Wayans said. “That conversation to me, it’s silly. It’s a negative thing that is only in Black people. We have for some reason been programmed to look down on the craziest parts about our spirits. We’re supposed to embrace our past, our history, our heroes, different levels of comedy.”
Wayans contrasts Black folks’ reaction to our famous men in drag with that of white people, who have a plethora of big- and small-screen heroes who have said yes to the dress: My namesake Dustin Hoffman is an unqualified legend who rocked drag in the Oscar-winning 1982 comedy “Tootsie.” Beloved comedian Robin Williams made his best film not named “Good Will Hunting” with the 1993 comedy “Mrs. Doubtfire,” which everyone born before 1987 enjoyed.
Tom Hanks, the World’s Most Unproblematic White Man™, donned a dress for the early 1980s sitcom “Bosom Buddies,” which launched his career. Each of the aforementioned white men have or had sterling, award-winning careers — and none of their white fans ever banged out a run-on paragraph in a comments section about “their” plan to emasculate the “white race.”
“But these Black men are forced to wear dresses to be successful,” you say? Well, let’s see: Eddie Murphy — arguably the greatest stand-up comedian dead or alive – had a career renaissance wearing drag in his wildly successful “The Nutty Professor” franchise in the late 1990s, a time when he was plenty rich and had all the creative free rein to do what he pleased.
Martin Lawrence dressed in drag for two characters, Ms. Payne and Sheneneh Jenkins, for his eponymous show…which, for my money, is one of the three best sitcoms ever created. Certainly, the creative buck stopped with Lawrence on that show, and he was also rich and famous enough to pass on the early-2000s “Big Momma’s House” franchise if he wanted to.
And, of course, Tyler Perry is the capo di tutti capi with nine zeroes in his net worth who still chooses to dress up as Madea because he can.
So even though Brandon T. Jackson said in a 2019 interview that rocking the dress in “Big Momma’s House” ruined his career, maybe it wasn’t the dress’ fault; perhaps Jackson needed to take cues from Foxx, who rocked a dress as Wanda in “In Living Color” and shimmied right into an Oscar a decade later with “Ray.”
The Black-men-in-dresses conversation is part of a larger zeitgeist-y discourse involving Black men who express themselves sartorially with gender-bending gear. Men like Jaden Smith, Young Thug and Kid Cudi wearing skirts and dresses cause folks to froth at the mouth and express their displeasure over the shadowy “they” seeking to push an “agenda” to emasculate Black men (even though no one can pinpoint who “they” is) instead of embracing the fact that these rich and famous creatives are wearing whatever the hell they please.
It may bring about pause to see presumably heterosexual Black men like Drake or Dwyane Wade wear nail polish, but these are wealthy men testing out new shit to see if it sticks – not agents of the Illuminati seeking to reduce our population by turning every Black man gay.
It may bring about pause to see presumably heterosexual Black men like Drake or Dwyane Wade wear nail polish, but these are wealthy men testing out new shit to see if it sticks – not agents of the Illuminati seeking to reduce our population by turning every Black man gay.
Many of us of a certain age should also recall that the early 1980s was a peak moment for straight Black men in mascara, eyeliner and pants so tight they probably lowered sperm count. Peep the late, great Charlie Murphy’s legendary Prince story on “Chappelle’s Show.”
It’s like everyone conveniently forgot that Prince pulled blindingly beautiful women while wearing blouses, thongs and ass-less chaps.
The conversation around famous Black men in drag is steeped in heteronormativity, patriarchy and, of course, white supremacy. It’s annoying that we still need to have it in 2024, and I implore you all to do better. And next time you run into Tom Hanks on the street, ask him how that whole wearing-a-dress thing 40-plus years ago worked out for him.
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