The Mean Girls of Black Hollywood: 15 Cross-Dressing Roles Portrayed By Black Actors

Lets face it, even in 2010 (and yes, even if you live in Atlanta), seeing a man dressed up as a woman takes some getting used to.

Yet, in film using the cross-dressing gimmick almost seems cliché, especially among Black actors.

Most of the roles are comical and warm hearted in nature.

However, that still doesn’t stop the debate as to whether or not all these cross-dressing characters (many portrayed by strong Black actors) contribute to the perceived “emasculation” of the Black man in America.

Tyler Perry’s Madea is the latest he/she role to cause conservative grumbles, but many a Black actor has earned his stripes by dressing up in polka dots.

Hate it or love it, here are 15 TV and film roles involving Black actors who swapped their button down for a blouse.

Is it just a part of the job, or a fail for black Hollywood?

Martin Lawrence

In what was arguably the funniest black sitcom ever, Martin added to the mile-a-minute laughs by dressing up and playing his obnoxious neighbor Sheneneh Jenkins and his callus mother Mama Payne.

In the quasi detective-comedy flick Big Momma’s House, Martin plays a detective who must suit up as Big Momma, a rambunctious country grandmother, in order to get to the bottom of a FBI sting operation.

Jamie Foxx

When Jamie Foxx was a newbie to the cast of In Living Color in the show’s waning years, he set his comedic presence apart from the crowd by playing the unforgettable character of LaWanda, a big-lipped country bumpkin who just wanted to be loved.

Wesley Snipes

In the 1995 cross-dressing cult flick, To Wong Fu, Thanks For Everything! Julie Newmar, Wesley Snipes slips on a dress and gets a tape job to portray drag queen Noxema Jackson as he and two other members of the…royal family take road trip.

Tyler Perry

The cornerstone of the Tyler Perry’s empire is the role of extremely aggressive black grandmother Mabel “Madea” Simmons, played by Perry himself.

Marlon & Shawn Wayans

The two youngest brothers of the Wayans comedic dynasty took it to the next level and slapped on more white powder than a LeBron James court entrance to play ditzy white girls Brittany & Tiffany Wilson in White Chicks.

Eddie Murphy

Eddie is known for taking on multiple roles in a single movie (think Coming To America) but the veteran comedian took on different gender roles in the 1996 film, The Nutty Professor, playing the cautious mother Mrs. Clump and the lustful granny, Grandma Clump.

Now used to the idea of wearing wigs, dresses, makeup and butt and breast pads, Murphy takes on the role Rasputia Latimore playing the fat, self-centered wife of his male role in Norbit.

Damon Wayans & David Allen Grier

One of In Living Color’s most notable sketches included Damon Wayans and David Allen Grier playing Blaine Edwards and Antione Maryweather, a sissy Siskel and Ebert who reviewed movies in the recurring skit, Men on Film.

Ricky Smiley

In the movie, First Sunday comedian Ricky Smiley brings one of his standup routines to life and dresses up as the old, docile church mother Bernice Jenkins.

Ving Rhames

In what is probably the most serious cross-dressing role, the usually rough and tumble Ving Rhames plays Holiday Heart a gay drag queen who befriends a single mother and her daughter and tries to protect them from the criminal element that surrounds them.