Drag in Cinema – The Early 2000s

Ving Rhames as Holiday Heart.

Holiday Heart 2000 TV movie

Holiday Heart, portrayed by Ving Rhames is a gay African American man who performs as a drag queen at a popular nightclub in Chicago. He is talented, tough, compassionate, and a dedicated Christian, despite his sexuality. After his boyfriend dies, he befriends a down on her luck, drug addicted, single woman, Wanda (Alfre Woodard) and her young daughter Niki (Jesika Reynolds). Holiday offers them a stable home and becomes a much-needed father figure for Niki. The story is a dramatic ride with drug addiction, central characters dying, teenage angst, and a chance for Ving Rhames to beat up some of the bad guys showing that just because you’re a gay queen doesn’t mean you can’t kick some butt.

The Nutty Professor II: The Klumps 2000

2000 saw Eddie Murphy return to the roles of female members of the Klump family in Nutty Professor II: The Klumps. We forgot to mention in our earlier column that The Nutty Professor, a remake of the 1963 Jerry Lewis film, came out in 1996 and that’s when Murphy played Mama Klump and Grandma Klump. He did in fact play all the members of the Klump family in both films. Murphy’s depiction of the Klump family females as overweight, unattractive old ladies fits in with the film’s overall theme of fat shaming. Add in many fart jokes and you know you’re in for a raunchy, and often hilarious, film experience. Murphy will return to portraying another fat woman, but one who is younger and expresses her sexuality freely, later in the first decade of the 2000s.

Martin Lawrence as Big Momma.

Big Momma’s House 2000

Perhaps inspired by Murphy’s success as a fat lady on film Martin Lawrence goes undercover as a grandmother, a fat grandmother named Hattie Mae Pierce. Lawrence is FBI agent Malcolm Turner an agent know for his ability to disguise himself in the course of investigations. When a convicted killer escapes from prison Turn and another agent are assigned to guard the home of Hattie Mae Pierce. She is the grandmother of the escapee’s former girlfriend and the FBI think he might show up there. All goes according to plan until Hattie Mae suddenly leaves town to attend to a sick friend for two weeks. It just so happens that agent Turner has brought his fat suit and wardrobe of grandmotherly dresses along. He takes her place and comedy ensues.

All the Queen’s Men 2001

A team of British Special Forces men must disguise themselves as women to infiltrate the all female-run factory in Berlin that makes the Enigma coding machines during WWII. The stars are Eddie Izzard and Matt LeBlanc. Izzard is the only actual transvestite with experience wearing women’s clothing. Oddly enough he plays Tony Parker, a British tranvestite, who has to whip the infiltration squad in to shape as women. The plot has a few twists and turns and drag fans will appreciate seeing Eddie Izzard, Matt LeBlanc and the other two infiltrators in ‘40s drag but Roger Ebert included the film in his book, Your Movie Sucks, saying it was “a perfectly good idea for a comedy, but it just plain doesn’t work.”

Miguel A. Núñez Jr. as Juwanna Mann.

Juwanna Mann 2002

Miguel A. Núñez Jr. plays Juwanna Mann/ Jamal Jeffries, the reigning ‘bad boy’ of basketball. His undisciplined on-court antics get him tossed out of the league and without any prospects. Financially strapped and untrained in anything but basketball, Jamal comes up with a plan so outrageous it just might work: dress up like a woman and try out for the woman’s basketball league. To his surprise, he makes it. But now he has to erase Jamal and start new life as Juwanna. Things get even more complicated when Juwanna realizes that “she” is falling for her teammate Michelle, who shows Jamal that there is more to women than meets the eye. The film treats Jamal’s female impersonation seriously. He doesn’t just show up in a scene perfectly dressed as Juwanna with no explanation of how he did it. His no-nonsense Aunt Ruby took him in after he lost everything and when he propose the idea of going out for the women’s team she helps him learn feminine skills. There is also an explanation of how he goes through the team physical exam without being found out. The film does use the trope of a male character so enchanted by the man dressed as a woman that he pursues “her” relentlessly but it does get some laughs. Jamal ends up as a better man and better basketball player in the end.

Sorority Boys 2002

The sorority boys.

Three frat boys who love the party lifestyle of their frat, and are in charge of the frat’s social life, do something that gets the frat president mad at them. He throws them out of the fraternity accusing them of stealing the frat member’s tuition money. One of the three has a secret camera in his room that he uses to record his sexual encounters with sorority members. (He is a dog at the start of the film.) The three take advantage of the frat’s “lady’s night” to dress as women and get back into the house to find the camera. (Unlike Juwanna Mann there is no explanation of how they do this.) This of course does not work out and they end up being taken for members of the Delta Omicron Gamma sorority who are not welcome in the frat house as they are seen to be “dogs” by the members of Kappa Omicron Kappa. After the boys dressed as girls are thrown out of KOK they pledge the DOG sorority. Then they begin to learn what how bad their old frat has been treating women, and especially the sister of DOG. There’s more to the plot and subplots that ensure rowdy fun. Of course the three former party animal dudes learn a lot about themselves by pretending to be women. Of the three actor Barry Watson looks the most believably female. Michael Rosenbaum has his sexy moments, and Harland Williams was the one who played it for the most laughs. Of course nowhere in the film is it acknowledged that even bad drag takes some skill. How do these frat boy party dudes find wigs, clothes that fit and learn to do makeup well enough that their sorority sisters don’t catch on?  For a further exploration of how silly the film is visit Roger Ebert’s film review site for a review by Ebert himself.

White Chicks 2004

Marlon Wayans as Tiffany.

Shawn Wayans as Brittany.

Shawn and Marlon Wayans are FBI agents who have messed up a sting and are assigned to guard two heiresses who are set to attend a fashion event in The Hamptons. There has been a rash of kidnappings of rich socialites and the Wayan’s characters are tasked with protecting the shallow daughters of Wilson Cruiseliner CEO Andrew Wilson. The young women are involved in a minor car accident and are so shallow they refuse to go to the fashion event with tiny scars marring their perfection. This leads the Wayans brothers’s characters to stash the girls in a hotel and impersonate thm at the event. Which means they have to adopt “whiteface” and mini skirts. Of course the FBI masters of disguise can’t convincingly take the place of two pampered white girls who are not as tall as them, for one thing, but since this is a Wayans movie there are a lot of laughs. The plot gets way(ans) complicated but it all works out in the end. Somehow the faux white chicks manage to get accepted as the women they’re impersonating for long enough and eventually the kidnapper is found and everyone goes shopping.

Drag in Cinema will be back next month and pick up in the middle of the first decade of the 21st century.

Tags: crossdressing, featured, History, Transgender

Category: Transgender Fun & Entertainment