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From Flip Wilson to Madea, Black male comedians in dresses are a Hollywood rite of passage

These characters can be funny, but also dangerous

We See Each Other, A Black, Trans Journey Through TV and Film, by Tre’Vell Anderson, is available now from Andscape Books. In this excerpt, they look at the history of Black male comedians wearing “women’s clothing” and what it does and doesn’t say about masculinity — and about the characters they portray.

It’s a recurring refrain in Hollywood that in order for a Black male comedian to truly make it big, he, seemingly, has got to put on a dress. Flip Wilson did it on his show as Geraldine in the ’70s and ’80s. Martin Lawrence and Jamie Foxx did it as Sheneneh on Martin and Wanda on In Living Color, respectively, in the ’90s. As did Eddie Murphy as Mama and Granny Klump in the Nutty Professor franchise, the first film of which won an Oscar for Rick Baker and David LeRoy Anderson’s makeup in 1997. Shawn and Marlon Wayans in White Chicks; Tracy Morgan and Kenan Thompson on Saturday Night Live; Miguel Núñez Jr. in Juwanna Mann; Brandon T. Jackson alongside Martin in the Big Momma’s House franchise; and Tyler Perry — they all did it in the 2000s and beyond.

Dave Chappelle notably did not do it. In a 2006 interview with Oprah, the comedian, who was widely criticized for his overtly transphobic Netflix comedy special fifteen years later, shared a story about refusing to do a scene in a Martin Lawrence movie that would’ve required him to wear a dress. Despite incessant prodding by the writer, director, and producers, Dave recalled, he stood firm that he was uncomfortable with the idea and ultimately “funnier than a dress.” Dave’s resistance has since been cited as a rejection of white Hollywood’s supposed ongoing effort to emasculate the Black man, cross-dressed characters being a leading example of a mass media conspiracy at work. Now, I might challenge the intellectual merits therein . . . but there are plenty of nig-nogs running around who agree, if proven by nothing other than the pilot episode of the Showtime series White Famous, which ran for a single season in 2017.

About an up-and-coming comedian, and produced by Jamie Foxx, whose own career inspired its concept, the cable series’ first episode centers on an opportunity presented to Jay Pharoah’s character to star in a big producer’s film as the old woman, à la Madea. Though Pharoah’s character finds the idea absurd, he consults a variety of folks, including Foxx (as himself), about the role. During a fantasy sequence in which the character does put on a dress, in a visual representation of said emasculation, his penis disappears.

Dating back to the not-so-long-ago history of this country when Black people were enslaved by white people, it is well documented the ways in which enslavers emasculated, or, some might say, dismantled the manhood of, Black men. Believing them to be physical threats, many enslavers came up with ways to strip Black men of what they perceived was their power. This included everything from castration to death. It’s been debated whether or not Black men donning wigs and dresses is castration by another name.

Jamie Foxx (left) as the character ‘Wanda’ in Living Color.

20th Century Fox Film Corp/Everett Collection

To be clear, in me and mine house, a Black man playing a Black woman character — dress, wig, or otherwise — is not an act of emasculation, of an individual or a community. Such a small-minded rendering of identity gives very much hotep energy, and it purposefully ignores and erases the liberatory divinity of the feminine and its ability and necessity to free us all. Not to mention, if what we’re to understand as Black manhood and masculinity, in particular, can be compromised simply by donning a muumuu or a wig, it is as fragile as it is toxic — and it might not be as worthy of protecting and maintaining as many might believe.

But because so much energy and discourse often begins and ends with a focus on the alleged emasculation of Pookie ’nem, not often enough do we get a chance to talk about the ways in which the women characters these Black men sometimes take on are never afforded the true humanity they’d like to believe is present — even when the characters are supposed to be actual women and not just a disguise. It’s not lost on me the ways in which this mirrors how Black women — trans and cis alike — are dehumanized IRL.

For the most part, almost every Black man who is famous for a woman character they’ve played has said their characters are inspired by women they, and we, know. For Tyler Perry, it’s his mother and aunt. For Martin Lawrence, it was the round-the-way, ghetto fabulous chicks named after luxury cars. The same for Jamie Foxx. While obviously comedy, at the core is said to be a love for and homage toward these types of women in our communities. Perhaps this is true. I’m actually sure it is. What is also true is that some of these characters are evolutions of what historian Donald Bogle titled his history of Black representation on-screen: “toms, coons, mulattoes, mammies, and bucks.”

And this, by the way, also goes for your favorite social-media influencer who’s built his following and career off of the same style of characters and caricatures as Tyler and Jamie and Martin and the rest of them. In one way or another, so many of these characters, though not all, ultimately mock a type of femininity and/or patronize a type of womanhood. Maybe not always in totality and just via a joke here or there. But I think it’s this confluence of issues — emasculation and how these characters might refract and reflect Black womanhood — that can negatively impact the livelihoods of Black trans women and femmes.

Swirling around every Black trans woman’s and femme’s coming out and moving through the world is the stench, both recognized and not, of the perceived emasculation of the Black man. To many, our lives are their worst fears made real. They think that we, having been assigned male at birth, were emasculated so much that we want to be women. And then how we show up, I think, is sometimes read as a comment on and indictment of cis femininity and cis womanhood — when many of us couldn’t be bothered! The result is potential ire from every which way in our community, and when that is put in conversation alongside historical conflations between men in wigs for performance purposes and trans people just living our lives, it, then, is difficult to say there is absolutely no anti-trans sentiment in the renderings of many of these characters played by some of your favorite male celebs.

Martin Lawrence as Sheneneh Jenkins in Martin.

Warner Bros./Everett Collection

And sure, the transphobia may not be intentional. But when so many of the recurring jokes and narrative beats are about some of these characters’ physicality — whether it’s their height or big hands or broad shoulders or hairy legs or facial hair, characteristics that, in a binary world, women are not supposed to have — I can’t help but recognize how the same punch lines on-screen become the very barbs thrown at trans women and femmes to invalidate our lived experiences. And they’re used by the (Black) men who are killing us to justify their actions.

When I detail my relationships to various media, I try to make space for the complex and complicado. It’d be disingenuous otherwise to not recognize that we, as trans people, can both be entertained by these characters who were foundational in our media diets and question the ways that they are complicit in the ongoing acts of violence we experience.

I’m not sure I’ll ever be able to not laugh at the absurdity and comedic brilliance that is Madea, particularly in those early plays. The character and Perry’s portrayal are deeply connected to so many aspects of my life that I hold dear — my granny, being a Southern Belle, my love-hate relationship with the Black church, the complexities of Black Hollywood. And yet still, it’s important that we all acknowledge how these characters y’all see as just comedic fodder manifest off-screen as sites of trauma, how the ways we laugh at them are connected to how y’all laugh at us trans people for even attempting to live as our authentic selves.

I can say that these characters and the jokes made at their expense become emotional and physical violence because I’ve been on the receiving end of them. Hell, I’ve internalized many of them so much that I throw them at myself before the world gets a chance to. It’s what plays on a loop in my mind when I’m trying on “women’s clothes” in a fitting room. It’s what I think of, quite instinctually unfortunately, right before I leave my home each day, my reminder to arm myself for what may come, said and unsaid.

These tropes we’ve come to know as commonplace in film and television, and onstage, aren’t us, though we’re being treated as if they are.