Rewind: A Wardrobe Full of Cinematic Cross-Dressing Goodness

'Big Momma's House 2' brings to mind some of Hollywood's greatest paeans to the art of drag.

Martin Lawrence again straps on the fake boobs and wig in "Big Momma's House 2," reprising his role as undercover FBI agent Malcolm Turner. Lawrence is part of a long, proud Hollywood legacy — and no, we're not talking about being arrested for assault. Instead, we're here to celebrate the grand cinematic tradition of men donning women's clothes. So toss on yer ma's housecoat and slippers and join us as we count down the top 10 drag movies.

[Note: This list excludes films where the drag queen is actually playing a female character (hence nothing starring Divine) or more serious films about gender issues ("Normal" and "Transamerica" are not drag films). The first film on our list purports to be a serious take on the topic, but as with all Ed Wood films, its original intent is moot.]

10. "Glen or Glenda" (1953)

In Ed "Plan 9 From Outer Space" Wood's most personal film, the "celebrated" auteur plays Glen, an otherwise "normal" guy who just loves to wear women's clothes, and pines for his fiancée's supremely soft angora sweater. In a parallel tale, Alan (Tommy Haynes) undergoes a sex change operation to become Anne (hence the film's alternate title, "I Changed My Sex"). As with all Wood's films, "Glen or Glenda" makes almost no sense and is padded with pointless stock footage and bizarre non-sequitur narration by Bela Lugosi. ("Beware! Beware of the big green dragon that sits on your doorstep. He eats little boys, puppy dog tails, and big, fat snails. Beware. Take care. Beware!")

But boy, is it a pink, fuzzy hoot.

9. "To Wong Foo Thanks for Everything, Julie Newmar" (1995)

Noxeema Jackson, Vida Boheme and Chi-Chi Rodriguez (not the golfer) are three transvestites who get stuck in a small Nebraska town while venturing from New York to L.A. Three drag queens? From New York City? Stranded in the sticks? Uh-oh! Sounds like some Middle Americans are in for a lesson in tolerance! This overly PC fantasy is mostly notable for its casting: Manly men Wesley Snipes, Patrick Swayze and Jon Leguizamo play against type as the dragsters, even if they look like they should be hosting "The View" rather than lip-synching Marlene Dietrich songs.

8. "Wigstock: The Movie" (1995)

Dubbed "a celebration of life, liberty and the pursuit of big hair," this raucous documentary by Barry Shils about the annual Wigstock drag festival in New York City lays (almost) bare the entire gamut of talent in the drag world, from the polished professionalism of Lypsinka and RuPaul to some who might've been better off singing into a hairbrush in the bathroom. In some ways, "Wigstock" is as much about New York City as it is men in dresses and high heels, interspersing interviews with passersby whose range of reactions nicely sews up the crazy quilt of Manhattan.

7. "The Adventures of Priscilla, Queen of the Desert" (1994)

The mid-1990s were a hot time for men in drag. This Stephan Elliott comedy tells of two drag queens — Guy Pearce (Leonard from "Memento") and Hugo Weaving (Agent Smith from "The Matrix") — and a transsexual (Terence Stamp of "Superman II" and "The Limey" fame) heading to a gig at Alice Springs, a remote resort in the Australian desert. The titular Priscilla isn't one of the performers, but rather the purple bus that transports them through the Outback as they stop and do their lip-synching routine for dumbfounded audiences. (The Aborigines, in particular, don't know what to think). The film boasts some spectacular cinematography of the beautiful Aussie locations.

6. "Victor/Victoria" (1982)

Slightly deviating from our theme of men dressing as women, this musical stars Julie Andrews as a woman masquerading as a man dressing as a woman. Julie plays Victoria Grant, a Paris singer in the 1930s who, under the tutelage of a flamboyant older stage vet (Robert Preston) becomes a nightclub sensation as "Victor," a faux drag queen. James Garner plays a Chicago nightclub owner who is internally conflicted over his burgeoning feelings for "Victor." The movie, while very much an old-fashioned musical comedy, does deal pretty honestly with issues of gender roles, sexuality and power.

5. "La Cage Aux Folles" (1978)

Renatto (Ugo Tognazzi) and Albin (Michel Serrault) are a gay couple living it up in St. Tropez as the owners of a drag nightclub. But when Renato's son, Laurent, gets engaged to a woman from a conservative politico family, the meeting of the future in-laws brings wacky chaos.

Renatto tries in vain to be as masculine as he can (imitating John Wayne's mannerisms) and asks Laurent's mother to come pose as his wife. But Renatto is unaware that Albin has decided to bring his drag queen stage persona into their real life as "Zaza," pretending to be Laurent's mother as well. Sound like a "Three's Company" episode? Well, it's a bit funnier than that, and infinitely funnier than the 1996 American version, "The Birdcage," starring Robin Williams and Nathan Lane.

4. "Tootsie" (1982)

It's tough to be a struggling actor in New York. Just ask Michael Dorsey (Dustin Hoffman), a temperamental guy so desperate for work that he disguises himself as a woman to get a role on a soap opera. While "Dorothy" becomes a sensation on the show, Michael's treatment by the producers (and society at large) gives him an inside look at the sexism and exploitation women frequently have to deal with. Meanwhile, Michael's fallen in love with his co-star Julie (Jessica Lange), but has to fend off the advances of Julie's amorous father (Charles Durning).

The trickiest thing about "Tootsie" is that, unlike many of the other films on this list, you really have to buy that everyone around Dorothy truly believes she's a woman (albeit an unattractive one). Hoffman's keen portrayal earned him an Academy Award for best actor.

3. "The Rocky Horror Picture Show" (1975)

When innocent young Brad and Janet (Barry Bostwick and Susan Sarandon) get lost in a storm, they come to an eerie castle looking for help. What they find is an annual bacchanalia hosted by Dr. Frank-N-Furter (Tim Curry), a sweet transvestite from the planet Transsexual in the galaxy Transylvania. Brad and Janet will never be the same, nor was anyone who experienced this quintessential cult classic in its heyday.

It's difficult to explain the cultural impact of "The Rocky Horror Picture Show" to anyone too young to remember pre-Internet, pre-cable times. In the 1970s, cult phenomena were truly underground: They had to bubble and gel and spread organically, through word of mouth and the alternative press. For many teenagers 30 years ago, this was their first exposure to the visual image of a flamboyant man clad in women's lingerie, espousing sexual liberation and cannibalism (not to mention throwing toilet paper at a movie screen). Ah, good times, good times.

2. "Hedwig and the Angry Inch" (2001)

One could argue this film shouldn't be on this list for two reasons: First, the character of rock star Hedwig is a transsexual, not a transvestite, and this movie is, for all its flash, humor and music, in the end quite serious. But Hedwig's botched transgender surgery leaves her neither male nor female, and, well, the film's just too amazing to omit.

Adapted from his off-Broadway show, "Hedwig" is writer/director/star John Cameron Mitchell's moving, personal tale of a quest for love and the feeling of being "whole." It could have been painfully maudlin if it weren't for the fact that it's so damn fun. The mostly glam-punk soundtrack puts most "real" bands to shame, the characters and production design are impossible to take your eyes off of and the movie careens from mockumentary to comedy to musical to drama with surgical skill.

1. "Some Like It Hot" (1959)

Billy Wilder's comedy masterpiece remains side-splittingly funny almost 50 years after it was made. Joe and Jerry (Tony Curtis and Jack Lemmon, respectively) are musicians in prohibition-era Chicago who have the misfortune to witness a mob hit. To get out of town, they dress in drag and become Josephine and Daphne, part of a musical girl group headed to Florida (suspension of disbelief is necessary, but pays off).

Enter "Jell-O on springs," Sugar Kane (Marilyn Monroe), the singer/ukulele player in the band, who becomes fast friends with the "girls," unaware that one of them (Joe) is fast falling in love with her. So Joe adopts yet another persona, that of "Junior," a wealthy oil magnate in order to woo the shapely siren. Meanwhile, "Daphne" has to fend off the pushy advances of Osgood Felding III (Joe E. Brown), an aging millionaire who just cannot live without "her." This screwball farce is wall-to-wall entertaining, with endearing performances, great music, hilarious slapstick and a precision-timed comic screenplay.

And yes, we left "White Chicks" off this list on purpose. OK, you can take the housecoat off now.

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