Is there some big conspiracy around Black male comedians and actors wearing dresses in their performances? Kat Williams has sure had a lot to say about the ‘phenomenon’ over the years, including on his Club Shay Shay podcast back in 2024. And while we probably need to take some of the info with a pinch of salt, there are many instances of Black male comedians and actors wearing dresses before becoming household names in Hollywood. That said, it’s certainly not the case with everyone. No judgment. Just facts. Check out the list below.
Arsenio Hall
It’s hard to forget Arsenio Hall in that red dress and matching red lippie in the first Coming to America movie.
Billy Porter
You likely don’t have to ask Billy Porter twice for him to rock a dress. He’s often worn ball gowns or ball gown-like attire on the red carpet and even in the Amazon Prime Video movie Cinderella.
Brandon T. Jackson
The third Big Momma’s House film had Brandon T. Jackson dressed up as a woman throughout most of the film.
Chris Tucker
Before the Rush Hour movies, Chris Tucker played the flamboyant, genderfluid Ruby Rhod in The Fifth Element. While he technically didn’t wear a dress, the outfits were definitely high-femme.
Chris Rock
Before the Oscars slap heard around the world, Chris Rock and Will Smith starred together in an episode of The Fresh Prince of Bel-Air. Rock played a comedian named Maurice, then switched into a leopard-print dress and wig to play the character’s sister, Jasmine.
Cuba Gooding Jr.
Boat Trip is widely considered one of the worst movies of Cuba Gooding Jr’s career. It’s also the film where he dressed up in a gold two-piece as part of a drag show performance.
Dave Chappelle
Dave Chappelle has spoken out about wearing a dress for roles where he believed it felt forced or was used to emasculate Black male actors. He did, however, wear a dress in Robin Hood: Men in Tights and maybe for a skit with Howard Stern (we never see a full-body shot).
Eddie Murphy
Eddie Murphy’s actually worn a dress while playing a few of his now-iconic characters from movies like The Nutty Professor and Norbit. In fact, we’re still traumatised by some of those images.
Flip Wilson
Flip Wilson is widely recognised as one of the first (or at least most prominent) Black comedians to wear a dress on TV. He had a character named Geraldine Jones that became one of his most popular personas.
Jamie Foxx
In Living Colour had so many outrageous and memorable characters. One fan-favourite was none other than Wanda. Of course, the “aesthetically challenged” woman was just Jamie Foxx in a dress and heavy makeup.
Jaleel White
Even the family-friendly show Family Matters had its share of cross-dressing moments. Then, child actor Jaleel White had to play Steve’s Southern belle cousin, Myrtle Urkel, in the show.
Kenan Thompson
If you’re a regular SNL watcher, chances are you’ve seen Kenan Thompson wearing a dress multiple times. He also wore a green dress to match country singer Reba McEntire at the CMT Music Awards back in 2010.
Kevin Hart
Kevin Hart wore a dress for an SNL skit back in 2013, after stating in multiple interviews that we’d never catch him wearing one on screen.
Kel Mitchell
Good Burger was one of Kel Mitchell’s most popular movies, and surprisingly, only one of the times he wore a dress on screen.
Marlon Wayans & Shawn Wayans
The Wayans brothers were completely unrecognisable as the Wilson sisters in White Chicks. It’s possibly one of their most beloved roles to date.
Martin Lawrence
Martin Lawrence often wore a dress for laughs in the ’90s and early 2000s. Some of his most iconic characters are Sheneneh Jenkins from Martin and Big Momma from the Big Momma’s House franchise.
Miguel A. Núñez Jr.
Miguel A. Núñez Jr played a former basketball player who disguises himself as a woman to join the women’s basketball league in Juwanna Mann.
Nick Cannon
In the early 2000s, Nick Cannon regularly played a character named Latanya. He even did a red carpet interview with the late Aaliyah in full drag.
Rickey Smiley
Katt Williams claims to be the reason Rickey Smiley had to wear a dress in the 2008 movie First Sunday.
Reginald Veljohnson
Reginald Veljohnson is another Black male actor whose character had to wear a dress on Family Matters.
Tyler Perry
Most of us are familiar with Tyler Perry’s Madea movies. The titular character helped make Perry a household name all over the world.
Tracy Morgan
SNL has probably been one of the biggest platforms for Black male comedians (or maybe every comedian) to dress in drag. Tracy Morgan, in particular, was tasked with tackling The View host Star Jones. Of course, he wore a wig and a dress on the show.
Ving Rhames
Ving Rhames took a step away from his typical macho man roles to play a drag queen in the film Holiday Heart. It was actually one of the roles where we got to see his full range as an actor.
Wesley Snipes
Another tough black male actor to take on a drag role (dress, wig, heels and all) is Wesley Snipes. He played Noxeema Jackson in the film To Wong Foo, Thanks for Everything! Julie Newmar. To be fair, he did have Patrick Swayze and John Leguizamo dressed up as women alongside him.
Will Smith
Will Smith has dressed as a female belly dancer as far back as Wild Wild West and as recently as the live-action Aladdin film.
