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Of the many topics Katt Williams sounded off on during his now-infamous appearance on Shannon Sharpe’s Club Shay Shay podcast in January, one he returned to repeatedly was the rash of Black male comedians who have worn dresses in movies and television. He spoke disapprovingly of this phenomenon while talking about Rickey Smiley and Tyler Perry — performers he said “can’t play a man to save their life†— and Martin Lawrence, who tried to cast Williams in a dress-wearing role in Big Momma’s House 2. Just recently, he rehashed this talking point during his February 29 appearance on The Joe Rogan Experience, quizzing the host to name “one person that ever wore a dress in Hollywood unsuccessfully†before making a hard-to-follow argument equating transgender identity with the pagan deity and demon Baphomet. Gossipy allure aside, these were not the most entertaining or insightful conversation about this particular topic to grace podcast platforms in recent memory. That distinction belongs to comedians Langston Kerman and David Gborie, who tackled it from every conceivable angle in the August 2023 episode of their podcast, My Momma Told Me, “Black Man in a Little Dress,†featuring Saturday Night Live’s Devon Walker as guest. Case in point: Only the latter of these episodes features an earnest attempt to rank the “Mount Rushmore of Black men in dresses.â€
Launched in 2020 on the Big Money Players podcast network, My Momma Told Me is a twice-weekly show about the “most exciting, groundbreaking, and sometimes problematic†conspiracy theories in the Black community. Over the course of 280-plus episodes to date, the podcast has dug into popular and obscure conspiracies, urban legends, and superstitions about the NBA being rigged, white people being alien to planet Earth, Khloé Kardashian being the biological daughter of O.J. Simpson, and more. During the podcast’s first year, when episodes dropped once a week, these theories were brought in by the show’s guests (featuring comedians like Quinta Brunson, Ayo Edibiri, and Hannibal Buress). Later, with the introduction of a second “Motherfuckin’ Mini Episode†each week in 2021, Kerman began investigating theories submitted by fans as well. Gborie joined as co-host in June 2022, and in the show’s current iteration, it’s not uncommon for he and Kerman to record full-length episodes without guests.
Each episode of My Momma Told Me begins similarly, with Kerman and Gborie taking turns introducing the show with a joke about a silly or unhinged conspiracy they want to prove before diving into the actual theory at the heart of the episode. In “Black Man in a Little Dress,†Kerman comes in hot. “We only know the name Crispus Attucks because of white people’s unquenchable thirst for Black death,†he says. “That n- - - - did nothing in the Revolutionary War. He didn’t contribute one bit. And for some fucking reason, they keep putting him in our history books. There’s no reason for us to know the first man who died in a war. They don’t do that for any other war.†Kerman, Gborie, and Walker take the opportunity to riff about Attucks’s backstory and legacy. “Now, who’s gonna dance after supper?†Gborie imagines the other racist Revolutionary War soldiers asked after hearing the news of Attucks’s death. “Who’s gonna play the spoons?!†Kerman adds. “I love, so much, that this podcast is on Will Ferrell’s network,†Walker chimes in. It’s an excellent distillation of the hosts’ on-air chemistry, also on display across the many clips of the podcast the pair post to social media.
But as much as the podcast is fueled by quick-paced banter, it’s elevated by its format, which is intentionally designed to facilitate good-faith, perspective-rich conversations about topics that traditionally lend themselves more to hot takes. Kerman is a dedicated researcher who makes it a point to present the best case for and against each conspiracy theory the show interrogates, irrespective of how shaky they may seem at first blush. The result can be genuinely educational, like in the December 2023 episode with comedian Rob Haze, in which Kerman finds a legitimate academic research paper to validate Haze’s theory that you can make a Black & Mild cigar less carcinogenic by removing its tobacco, shaking it up, and rerolling it; or in the October 2022 episode with comedian Mandal, in which Kerman is unable to find evidence of Mandal’s theory that someone died doing the “Lean Wit It, Rock Wit It†dance, but does find evidence of a fascinating historical event called “the dancing plague of 1518,†during which hundreds of people in France danced uncontrollably for weeks for mysterious reasons, resulting in several deaths. Gborie, meanwhile, is always at the ready to provide color commentary about this research, or in the absence of that, a well-timed audio drop from his soundboard.
In “Black Man in a Little Dress,†this all culminates in an engrossing, laughter-dense conversation about the titular conspiracy theory at hand: the idea that there is a Hollywood shadow branch maliciously trading career opportunities to Black men based on their willingness to emasculate themselves by wearing dresses onscreen. “They get that dress on you yet?†Walker remembers an Uber driver asking him after finding out he performs stand-up. “I see you doing good, but I know you probably want to get to that top level, and you know what they’re about to make you do …†he remembers a jeweler unsolicitedly cautioning him. Walker, Gborie, and Kerman note that they don’t have any moral or philosophical objections to the idea of anyone wearing a dress if they want to, but at the same time, their progressive values don’t always shield them against the stigma others attach to this act. As Gborie puts it succinctly, “People got uncles.â€
But why is this conspiracy theory so prevalent? It’s a tricky question to unpack. Kerman reads out a long list of every Black male comedian who has worn a dress onscreen to illustrate why some might think this phenomenon is more than a coincidence, but Gborie is quick to point to Mrs. Doubtfire as evidence that many white male comedians have done it too. They revisit the infamous 2006 Dave Chappelle interview with Oprah Winfrey, in which Chappelle talks about being ambushed on the set of his movie Blue Streak with unnecessary new script pages that called for him to wear a dress in a scene, but they allow for the possibility that the people who added these were just typical meddling hacks. Plus, they leave room for the explanation that, in some instances, it’s just an entertaining plot device. “Who didn’t they get? Pretty much just Patrice O’Neal,†Gborie says at one point. “He would be hilarious in a dress! Objectively.â€
And the underlying assumptions behind this theory about what constitutes “emasculation†don’t get left unchecked. Toward the end of the episode, Kerman puts a bow on the trio’s discussion with an eloquent summary of their feelings. “At the root of it, a dress is not necessarily emasculation,†he says. “A dress is a dress. And you can be masculine inside of a dress, but our own homophobia and years of conditioning make us see it as a version of emasculation. And that’s what makes this complicated. It’s not the dress itself that makes us weaker. It is our own sense of self that makes us weaker, and a dress is just our articulation of that.â€
While this would have been an standout episode of My Momma Told Me even if Katt Williams hadn’t reignited conversation about its theme on Club Shay Shay a few months later, the reality is that he did, and everyone from Marlon Wayans to Eddie Griffin to Katt Williams again has made headlines for commenting on it in the aftermath. But if “Black Man in a Little Dress,†makes one thing clear, it’s that this isn’t a discussion that can adequately play out in headlines. It’s what makes My Momma Told Me such a valuable platform. Kerman and Gborie always strive to tell the full story.
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