The idea pops up every few years, then explodes again when Katt Williams starts talking. On Club Shay Shay in 2024, he pushed the claim that Hollywood nudges Black male comedians toward dresses before fame follows. You’ve seen the clips. You’ve seen the memes. You’ve also seen the exaggeration. Some stories wobble. Others line up with real filmographies and dates. What matters is pattern, not panic. Eddie Murphy did it. Martin Lawrence did it. Dave Chappelle didn’t. Neither did Denzel Washington. Below, you’ll find examples, context, and timelines, laid out clean. Read it, and make up your own mind.
Arsenio Hall Wore A Dress In Coming To America
It’s hard to forget Arsenio Hall in that red dress and matching red lippie in the first Coming to America movie.
Billy Porter Is Famous For Wearing Dresses On The Red Carpet And In Cinderella
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 Dressed As A Woman In Big Momma’s House 3
The third Big Momma’s House film had Brandon T. Jackson dressed up as a woman throughout most of the film.
Chris Tucker’s Ruby Rhod In The Fifth Element Blurred Gender Lines
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 Wore A Dress On The Fresh Prince of Bel-Air
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. Performed In Drag In Boat Trip
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’s Controversial History With Wearing Dresses In Hollywood
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 Played Multiple Female Characters In The Nutty Professor And Norbit
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’s Geraldine Jones Was One Of TV’s First Drag Comedy Characters
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 Created Wanda On In Living Color
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 Played Myrtle Urkel On Family Matters
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 Has Worn Dresses Multiple Times On Saturday Night Live
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’s Dress Sketch On Saturday Night Live
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 Wore A Dress During His All That And Good Burger Era
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 And Shawn Wayans Transformed Into The Wilson Sisters In White Chicks
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’s Most Famous Characters Included Sheneneh And Big Momma
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. Starred In The Cross-Dressing Comedy Juwanna Mann
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 Performed In Drag As Latanya Early In His Career
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 Wore A Dress In The Comedy First Sunday
Katt Williams claims to be the reason Rickey Smiley had to wear a dress in the 2008 movie First Sunday.
Reginald VelJohnson Had A Drag Moment On Family Matters
Reginald Veljohnson is another Black male actor whose character had to wear a dress on Family Matters.
Tyler Perry Built A Billion-Dollar Franchise With Madea
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 Wore A Dress On Saturday Night Live As Star Jones
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 Played A Drag Queen In Holiday Heart
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 Played Noxeema Jackson In To Wong Foo, Thanks for Everything! Julie Newmar
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 Wore A Belly Dancer Outfit In Aladdin
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.
