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Geraldine Jones
FLIP WILSON AS GERALDINE JONES ON THE FLIP WILSON SHOW (1970-1974)
Reason for cross-dressing: To please the white man Strictly for comedic purposes.
Complex says: In 1970, Flip Wilson broke barriers by being the first black star to host his own variety television show. In the show’s prime, it was the second most watched program in the United States, and Flip was presented as “TV’s First Black Superstar” on a Time magazine cover in 1972. But, more importantly, well for the sake of this list at least, he was the first major black comedian to appear in drag, with his portrayal of the sassy Geraldine Jones. It quickly became one of his more popular sketches (the video above shows him with the G.O.A.T., Muhammad Ali). The show eventually got canned in '74 due to a dwindling audience but Wilson's—or better yet Geraldine's—legacy forever rest with him proudly wearing those pumps and then passing those shits down.
Wanda Wayne
JAMIE FOXX AS WANDA WAYNE ON IN LIVING COLOR (1991-1994)
Reason for cross-dressing: Eh, because someone on the show had to do it.
Complex says: Twenty years ago Jamie Foxx popped on the scene wearing lipstick, a dress, and a blonde wig, playing "the ugliest woman in the world," Wanda Wayne. Now it's 2010, and our boy Jamie is a major movie star with an Oscar, so that means he has the option to play any part he wants. And with that being said, his next role will be...Wanda Wayne, “the ugliest woman in the world.” That's progression, baby! Foxx and Martin Lawrence (we'll get to him soon) will be resurrecting their drag queen personas in Skank Robbers, which we think is about them being some kind of bank robbers or some stupid shit like that. We guess Jamie put it best himself when he said, "Yeah, sometimes you gotta go make that money." Foreaaaal though!
Sheneneh Jenkins
MARTIN LAWRENCE AS SHENENEH JENKINS ON MARTIN (1992-1997)
Reason for cross-dressing: Again, for comic relief purposes.
Complex says: From the first episode to the last, Sheneneh, Martin and Gina’s nosy neighbor, was a major presence, quickly becoming a highlight on the show (for a while, at least). She would become so popular that 20 years later she would co-star in a major movie, even if that major movie is The Skank Robbers, that’s still impressive. The instant popularity of Sheneneh would lead to another popular crossing-dressing character on Martin…
Edna "Mama" Payne
MARTIN LAWRENCE AS EDNA "MAMA" PAYNE ON MARTIN (1992-1997)
Reason for cross-dressing: Well, Sheneneh worked, right?
Complex says: ...MAMA PAYNE! Similar to Sheneneh, Mama Payne quickly became one of the most popular characters on Martin, and it was all really due to Lawrence's outrageous portrayal of these two. In fact, you get the feeling that Martin could have even played Gina if he wanted to. (This actually might have been quite useful since Tisha Campbell, the actress who played Gina, would eventually sue Martin for sexual harassment.)
Noxeema Jackson
WESLEY SNIPES AS NOXEEMA JACKSON IN TO WONG FOO, THANKS FOR EVERYTHING! JULIE NEWMAR (1995)
Reason for cross-dressing: Affirmative Action. The movie was about a trio of drag queens, and a white guy and a Spanish dude were already involved, so it was only fair.
Complex says: After 1994's Sugar Hill, shit took a dark, dark turn for Wesley Snipes. The first sign something was wrong was this one-gag dud. This was clearly a situation where producers just gave up and said, "Hey, fuck a story or a plot. Lets just throw some dudes in a dress and have them go on a road trip. And let's get a black dude in there!" Man, Wesley should have never picked up the phone.
Mama Klump & Grandma Klump
EDDIE MURPHY AS MAMA KLUMP AND GRANDMA KLUMP IN THE NUTTY PROFESSOR (1996) AND THE NUTTY PROFESSOR II: THE KLUMPS (2000)
Reason for cross-dressing: Because Mo'Nique wasn’t a star yet.
Complex says: The Nutty Professor saw development: Suddenly we went from black dudes dressing like women to black dudes dressing like fat women. For some reason, future producers thought adding 300 pounds would make this joke funnier. Nope, this gag was smelly hot air by the time Eddie was done with it.
Hattie Mae "Big Momma" Pierce
MARTIN LAWRENCE AS HATTIE MAE “BIG MOMMA” PIERCE IN BIG MOMMA’S HOUSE (2000), BIG MOMMA’S HOUSE 2 (2004), AND BIG MOMMAS: LIKE FATHER, LIKE SON (2011)
Reason for cross-dressing: FBI agent Malcolm Turner dresses up like a fat woman because he's undercover, investigating a bank robbery. Or maybe it's because the producers realized that Eddie Murphy dicking around in a fat lady suit raked in over $200 million at the box office.
Complex says: Yeah, there was some serious swagger jacking going on over here. What made matters worse is that this movie came out around the same time as the sequel to The Nutty Professor movie. Not Martin's proudest moment.
Holiday Heart
VING RHAMES AS HOLIDAY HEART IN HOLIDAY HEART (2000)
Reason for cross-dressing: The main character, Holiday Heart, is a drag queen.
Complex says: This made-for-TV tear-jerker is not a comedy, nor is Ving Rhames really considered a comedian. Still, we threw him on here because he matches two criteria: He’s a black dude and he had to deal with lady Spandex putting a death grip on his crotch.
Maya Angelou (Tracy Morgan)
TRACY MORGAN AS MAYA ANGELOU ON SATURDAY NIGHT LIVE (2002)
Reason for cross-dressing: Saturday Night Live hardly ever has black female cast members.
Complex says: Random SNL fact for y'all: In the show's history, there have been only four black women in the cast (Danitra Vance, Yvonne Hudson, Ellen Cleghorne, Maya Rudolph). But it's just the darndest thing, black women keep on making news. So what does the show do to compensate? Find out the dress size for the token black guy, of course! SNL has been as flagrant as anyone over the years with its drag antics, and from 1996 until 2003, Tracy Morgan was the token black guy. In this instance, Morgan does his portrayal of poet Maya Angelou, who has been played so many times by so many black actors over the years (David Alan Grier famously pimped out Butterfinger bars as Angelou) that you’d think they get a comedian just to play her. You're next, Jay Pharoah.
Juwanna Mann
MIGUEL A. NUNEZ JR. AS JUWANNA MANN IN JUWANNA MANN (2002)
Reason for cross-dressing: Jamal Jeffries, is a professional basketball player who gets kicked out of the NBA. His only hope to salvage his career is to dress like a woman, name himself Juwanna Mann, and play in the WNBA. Ugh, we feel cheap just summarizing this stupid shit.
Complex says: What a terrible movie this was. How could they think this was a good idea? Even without the shitty cross-dressing element, in essence this movie is really just a woman's basketball flick. It is an untapped market for a reason, people! Sidenote: Miguel A. Nunez Jr. is probably the most convincing drag queen on this list; we honestly can't tell the difference between him and a real WNBA player.
Brittany & Tiffany Wilson
SHAWN AND MARLON WAYANS AS BRITTANY AND TIFFANY WILSON IN WHITE CHICKS (2004)
Reason for cross-dressing: The Wayan's brothers play two FBI agents who disguise themselves as two rich heiresses to protect them. Imagine if the Feds really did shit like this? We'd want tax money back.
Complex says: Another evolutionary moment in drag history: Black guys disguising themselves as white women. Reverse Racism? Maybe. All we know is this really didn't catch on like the fat suit did, which is surprising considering how popular white women in Hollywood have become over the years.
Mabel "Madea" Simmons
TYLER PERRY AS MABEL “MADEA” SIMMONS IN DIARY OF A MAD BLACK WOMAN (2005)
MADEA'S FAMILY REUNION (2006), MEET THE BROWNS (2008), MADEA GOES TO JAIL (2009), AND I CAN DO BAD ALL BY MYSELF (2009)
Reason for cross-dressing: There is no apparent reason for Tyler Perry to play this matriarch.
Complex says: Tyler Perry is as polarizing a black actor as you can get. Black women love his work (which is kind of ironic, since his playing Madea takes one more role away from a black actress) but outside of that circle there have been numerous critics of his programs. We won't say it, but Spike Lee’s ether a couple of years ago sums up the criticism pretty nicely. Still, Perry has made himself a fortune with Madea. You can always buy self-respect, right?
Lola
CHIWETEL EJIOFOR AS LOLA IN KINKY BOOTS (2005)
Reason for cross-dressing: Ejiofor actually plays a stylish drag queen.
Complex says: Kinky Boots is a movie about a dude who saves his family shoe business by manufacturing heels for drag queens. It didn't catch too many American moviegoers' eyes, but Chiwetel Ejiofor in a wig and pumps didn't escape our eyes either.
Rasputia Latimore
EDDIE MURPHY AS RASPUTIA LATIMORE IN NORBIT (2007)
Reason for cross-dressing: Eddie Murphy was in straight cash grab mode.
Complex says: Norbit has to haunt Eddie Murphy. It just has to. Murphy was damn near guaranteed an Oscar for his role as James "Thunder" Early in 2006’s Dreamgirls. Then this monstrosity of a movie was released, right around the time the Academy was making its decision. Oscar dream dead and buried. The movie was a disaster in every conceivable way. Well, except one. The shit made money—it pulled in more than $100 million in its box office run. So, actually, maybe this doesn’t haunt Murphy that much after all.
Barbara Birmingham
KENAN THOMPSON AS BARBARA BIRMINGHAM ON SATURDAY NIGHT LIVE (2007)
Reason for cross-dressing: Because Kenan became SNL's token black actor in 2003.
Complex says: OK, so this is the beginning of our Kenan Thompson portion of our list. First up to bat: Thompson as the spank-happy nanny, Barbara Birmingham. You want more Kenan? Sure you do! Keep clicking...
Virginica Hastings
KENAN THOMPSON AS VIRGINICA HASTINGS ON SATURDAY NIGHT LIVE (2008)
Reason for cross-dressing: Again, token black guy.
Complex says: For some reason unknown to us, Virginica has become one of Kenan's more popular characters. Kenan's character really is what would happen if every other drag queen in this list morphed together to make one big blob of man-bitch.
Bernice Jenkins
RICKEY SMILEY AS BERNICE JENKINS IN FIRST SUNDAY (2008)
Reason for cross-dressing: Chalk it up to comic relief. Again.
Complex says: If you didn't know, Rickey Smiley is a comedian and radio personality who's best known for his prank calls. One of his more memorable characters is old lady Bernice Jenkins. She (or he?) makes a short appearance in Ice Cube's First Sunday. We're just letting you know because there is a very good chance that you didn't see this one.
Maya Angelou (Kenan Thompson)
KENAN THOMPSON AS MAYA ANGELOU ON SATURDAY NIGHT LIVE (2009)
Reason for cross-dressing: Kenan. Token. Black. Comic. Dress. Wig. SNL.
Complex says: Annnnnnnd, now we're back to Kenan. Without David Alan Grier or Tracy Morgan to Maya Angelou, there was really only one person to play her. Since we have actually never seen this Maya Angelou, we're not sure who resembles her most.
Whoopi Goldberg
KENAN THOMPSON AS WHOOPI GOLDBERG ON SATURDAY NIGHT LIVE (2010)
Reason for cross-dressing: Sigh...
Complex says: Actually, Kenan was pretty memorable as Whoopi during The View sketches, so we'll give this one a pass. Um, maybe.
Mo'Nique
KENAN THOMPSON AS MO'NIQUE ON SATURDAY NIGHT LIVE (2010)
Reason for cross-dressing: There's good reason here; Kenan actually bears a striking resemblance to Mo'Nique.
Complex says: At this point, we're convinced the only items in Kenan's wardrobe closest are heels and various mumus.
Charmaine Daisy Pierce
BRANDON T. JACKSON AS CHARMAINE DAISY PIERCE IN BIG MOMMAS: LIKE FATHER, LIKE SON (2011)
Reason for cross-dressing: Jackson, who plays Lawrence's son, witnesses a murder and must disguise himself as Big Momma's niece to hide from his would-be murderers.
Complex says: Brandon T. Jackson is black and has a nice blossoming career going for him, so it was inevitable that we catch him in a dress. Now here's the sick shit: No matter how terrible this movie looks (and really, just take a glance at that trailer) you know it's going to be a hit. Why? Because the first two were huge. Which just tells us this shit will never stop.