Ever since Flip Wilson put on a dress as Geraldine Jones, audiences have been clamoring for black guys in drag. In case you’ve just caught cross-dressing fever, here’s a list of 10 films you may want to explore.
Please keep in mind that many of these movies are otherwise awful productions, with the obvious sight gag overpowering any need for well-written comedy or coherent plot. And before anyone starts complaining about a shortage of Tyler Perry movies, just remember that a whole list could be dedicated to his portrayal of Mabel “Madea“ Simmons. In fact, maybe I’ll do one in the near future.
- Big Momma’s House (2000) – Assigned to track down escaped killer Lester Vesco (Terrence Howard), FBI agent Malcolm Turner (Martin Lawrence) is forced to don a dress, wig, and fat suit to impersonate Hattie Mae “Big Momma” Pierce, the grandmother of Vesco’s ex-girlfriend and one-time partner in crime, Sherry Pierce (Nia Long). But when Sherry and her son come to visit, Malcolm will have to pull off the role of a lifetime, especially since he finds himself falling for her. Co-stars include Paul Giamatti, Anthony Anderson, and Cedric the Entertainer.
- Big Momma’s House 2 (2006) – Baby’s got back…again! While critics hated this Martin Lawrence sequel even more than the original, ticket sales helped it gross nearly $140 million at the box office. Lawrence reprises his role as FBI agent Malcolm Turner, and this time around he’s expecting his first child with wife Sherry (Nia Long). But when an old pal is killed in the line of duty, Malcolm once again dons the Big Momma disguise to infiltrate the home of a suspect. Applying for a nanny position, Big Momma is soon teaching life lessons to a trio of kids (including Kat Dennings and Chloe Moretz) and proving that the morbidly obese–fake or otherwise–should never wear a bikini. Co-starring Marisol Nichols, Zachary Levi, and Emily Procter, it usually ranks among the worst films rated on the Rotten Tomatoes website.
- White Chicks (2004) – When a pair of FBI brothers, Kevin and Marcus Copeland (Shawn and Marlon Wayans), screw up an assignment, they’re given one last chance to save their jobs. Their latest mission centers around protecting a pair of rich socialites targeted for kidnapping, but the brothers find themselves in a pickle when the girls refuse to leave their hotel rooms. Desperate to stay employed and catch the kidnappers, they rely on the local mall and plenty of make-up to transform themselves into bitchy Caucasians. Meanwhile, Marcus’s wife begins to suspect that he’s having an affair, and Kevin tries to romance a news reporter. Co-starring Busy Philipps, Jaime King, Brittany Daniel, Terry Crews, and John Heard.
- Juwanna Mann (2002) – Miguel A. Nunez, Jr. stars as Jamal Jeffries, a selfish pro basketball player who gets suspended indefinitely after taking off his clothes during a game. Fired by his agent (Kevin Pollak) and unable to find work, he takes the next logical step: dressing up like a woman and playing in the WUBA (this film’s version of the WNBA). But as a member of the Charlotte Banshees, the self-centered Jamal slowly begins a transformation thanks to his hard-working teammates (not to mention a little romantic tension). Co-starring Vivica A. Fox, Ginuwine, and Tommy Davidson. The perfect solution for those who love sports movies and black guys in drag.
- Madea Goes to Jail (2009) – Tyler Perry takes on three roles–including that of the popular and hell-raising Madea–in this comedy-drama that was a big hit with audiences. While a subplot deals with an attorney’s (Derek Luke) efforts to help a young prostitute (Keshia Knight Pulliam), much of the film deals with Madea’s anger issues and the problems she encounters because of it. Watch Madea go after a car with a forklift, butt heads with Judge Mathis and Dr. Phil, and have a showdown with a SWAT team. If you’re a fan of sassy black women, add this one to your collection immediately. Featuring cameos from Whoopi Goldberg, Al Sharpton, Tom Joyner, and Steve Harvey.
- To Wong Foo, Thanks for Everything! Julie Newmar (1995) – After winning a trip to Los Angeles, two New York drag queens (Patrick Swayze and Wesley Snipes) buy a vintage Cadillac and take their young protégé (John Leguizamo) along for the ride. But their car winds up stranding them in a small town, and they have plenty of opportunities to interact with the curious locals while waiting for repairs. A number of real-life drag queens make cameos (including Ru Paul), and the supporting cast includes Stockard Channing as an abused wife, Chris Penn as a homophobic sheriff, and Julie Newmar as herself. While it doesn’t feature any black guys in drag, also be sure to check out The Adventures of Priscilla, Queen of the Desert.
- The Longest Yard (2005) – Adam Sandler stars as Paul Crewe, a disgraced former NFL quarterback who gets sent to prison and is forced to put together a team made up of convicts. A remake of the 1974 Burt Reynolds’ classic football movie, this version co-stars Chris Rock, James Cromwell, Nelly, William Fichtner, Bill Goldberg, Michael Irvin, Bob Sapp, Terry Crews, Steve Austin, and Cloris Leachman. Tracy Morgan qualifies the film for “black guys in drag” status by portraying a comical prison sissy known as Ms. Tucker.
- Holiday Heart (2000) – Robert Townsend directed this Showtime movie about a gay drag queen (Ving Rhames) who befriends and tries to protect a drug addict (Alfre Woodard) and her young daughter. While the though of Ving Rhames in drag may sound comical, this is actually a well-made tear-jerker with plenty of moral lessons for viewers. Mykelti Williamson co-stars as a homophobic drug dealer.
- Nutty Professor II: The Klumps (2000) – Eddie Murphy reprises his role as the lovably inept scientist Sherman Klump, but he also plays most of Sherman’s off-the-wall relatives. After once again transforming into his oversexed Buddy Love alter-ego (see the first film for more), Sherman decides to get rid of him permanently by isolating and removing the responsible DNA from his body. This results in Buddy Love becoming a separate person, as well as Sherman rapidly losing his brain cells. Can the situation be resolved before it wrecks Sherman’s chances at marrying a fellow scientist (Janet Jackson)? Co-starring Larry Miller, Wanda Sykes, and John Ales.
- Norbit (2007) – Norbit Albert Rice (Eddie Murphy) grew up in an orphanage owned by Mr. Wong (Eddie Murphy). His best friend was Kate (Thandie Newton), but she was eventually adopted. When the other kids started giving the nerdy Norbit a hard time, he was protected by the obese and overbearing Rasputia (Eddie Murphy, again). Years later, the couple are married, and Rasputia takes every opportunity to dominate and belittle her man. Then Norbit sees Kate again for the first time in years, and the sparks soon fly. But Rasputia won’t go away so easily, nor will the plot by her three brothers to buy the orphanage and convert it into a strip club. The critics called it “cruel” and “crass,” but fans of black guys in drag will call it paradise. Co-starring Terry Crews, Eddie Griffin, Cuba Gooding, Jr., and Marlon Wayans.
So while Dave Chappelle complains about the practice and audiences laugh their heads off, settle into your favorite chair and pop in a film about black guys in drag. You’ll be transported into a magical realm where Wesley Snipes has blonde hair (no, not Demolition Man), Eddie Murphy is a morbidly obese shrew, and Martin Lawrence dons both a fat suit and a skimpy bikini. “Halleluyer praise da lort!”