Or, the clothes make the man (look like a woman or the woman look like a man)
As I promised last night, while reflecting on the cross-dressing tendencies of the females of our household, I’ve put together a list of some cross-dressing instances in theater, film and TV. The entertainment media show us a host of reasons for donning the garb of the opposite gender. Whether it’s a lifestyle choice, or for some pragmatic or work-related reason, we see a variety of possible benefits.
The list below is a bunch of movies, shows and plays that feature some sort of cross-dressing, that have further been tagged and sorted by additional features.
1. We have two main types, as in two main genders. So representatives will be tagged:
and
2. (kaw) Also note that a lot of these movies and shows also have been highlighted in lists of my kick-ass women project, so I’ll tag them, too. Especially those involving women dressing in men’s clothes. (Coincidence?)
Movies, shows and plays that feature cross-dressing
1. First, we have movies featuring transgendered or transexual folk:
- Some dramas:
Ed Wood stars, Ed Wood directs. Ed Wood wears fuzzy angora sweaters. Known (as are all of Ed Wood’s films) as a wonderfully bad movie. I need to see this some time.
Yes, I know I just spoiled the surprise ending.
Hilary Swank plays a teenage boy who was born biologically female. (Another one I haven’t seen. I hear it’s very good.)
- Drag Queens of the stage:
Chiwetel Ejiofor plays Lola, a drag queen who needs some new shoes.
Nathan Lane plays a stage queen. Also pretends to be a woman off the stage to fool some folks.
Haven’t actually seen these. “The Bird Cage” was based on the first one. The second involves man pretending to be woman pretending to be man, from what I understand.
- Road-tripping drag queens:
A drag queen goes on an Australian road trip.
Wesley Snipes, Patrick Swayze, John Leguizamo as drag queens in an American road trip movie.
2. Often, cross-dressing can be a work-related activity. In many cases, it can be about landing a job:
- For example, for men who aspire to become a nanny, it may be helpful to pretend to be a woman:
Robin Williams impersonates a woman to land a role as his kids’ nanny.
Ther was a story arc about Mrs. Featherbottom: Tobias (David Cross) “disguises” himself as a woman to play a nanny in the spirit of Mrs. Doubtfire. His family pretends to be fooled because they got a cleaner house out of the deal.
- Police and spy jobs often require clever disguises for undercover work. And what could be more cleverly disguising than opposite-gendered apparel?
Periodically, the men/detectives of the cast/department dress up (unconvincingly) as women in order to entrap potential solicitation offenders, muggers, or others.
Cameron Diaz and Drew Barrymore disguise themselves in suits and facial hair to infiltrate a tech company.
Shawn Wayans and Marlon Wayans play FBI agents. Two (black) dudes masquerade as two (white) chicks. For some reason or another. (Haven’t seen it.)
Uncle (Bill Tung) makes an appearance as the mother of Jackie Chan and Michelle Yeoh, who are pretending to be brother and sister for an undercover assignment.
Jackie Chan makes a cameo. In drag. I’m not really sure why.
- Getting into, or out of, the military by way of getting into transgendered clothing:
Klinger (Jamie Farr) spends several seasons dressing in women’s clothes to try to get out of the army.
A girl pretends to be a boy in order to join the army.
The episode with balls. Bouncing balls. (Called “War is the H-word”) Leela disguises herself as a man to join the army to keep an eye on Fry and Bender (who joined the army to get a discount on gum.)
- Getting onto the screen or stage:
Set in Elizabethan England, when/where only men were allowed to act on the stage. Gwynneth Paltrow pretends to be a young man in order to land a role in Shakespeare’s new play.
Dustin Hoffman dons wig and dress to land a soap opera role.
Julie Andrews plays a (male) female impersonator.
Leslie Chung (a man, by the way…ambiguous name and all) plays an actor in the Peking Opera who plays female roles on the stage.
- And like for the Peking Opera and the Shakespearean stage, sometimes real-life actors in more recent times play roles of the opposite gender:
The play written by J. M. Barrie. Stage performances of this play written by J. M. Barrie commonly feature women (Maude Adams, Mary Martin, Sandy Duncan) playing the lead role, a boy.
The young boy, Wong Fei-Hung, is played by a girl (Sze-Man Tsang).
- There’s the related sketch comedy tradition:
The chaps (Graham Chapman, Terry Jones, Michael Palin and Eric Idle) don dresses, and speak in sqeaky voices. (I don’t remember Terry Gilliam ever appearing in a dress.)
The kids (Dave Foley, Scott Thompson, Mark McKinney, Bruce McCulloch and Kevin McDonald) wear a lot of dresses, and a lot of wigs. And sometimes make very convincing women.
3. And finally, we have a bunch of miscellaneous reasons for cross-dressing. Prizes! Disguises! Housing! Respect! Modesty!
The episode where Dave Foley wins a costume contest by donning a wig and a little black dress. A bit of a tribute to his Kids in the Hall days.
Zhang Ziyi runs off with a stolen sword and disguises herself as a young man. (Leading to that incredible scene where she fights a restaurant-full of men. And trashes the restaurant. Not that I condone the trashing of restaurants. I just love that scene.)
Play by Shakespeare. Made into bunches of movies, including She’s the Man (2006). Woman Viola pretends to be her brother. (I’m not actually sure on the motivation for this. Shamefully haven’t read or seen the play. Or movies.)
Haven’t seen it. High school gal pretends to be a high school guy in order to be taken seriously.
Tony Curtis and Jack Lemmon disguise themselves as women to hide out from the mob. (And get to hang out with Marylin Monroe.)
Peter Scolari and Tom Hanks pretend to be women in order to get a good apartment.
Daryl Hannah plays a mermaid who arrives in New York City without a wardrobe of her own. Staying at the apartment of Tom Hanks (not the one shared with Peter Scolari), she puts on one of his suits before heading out for a shopping expedition in order to avoid further displays of public nudity.
collecting tokens 
The episode with balls. Bouncing balls. (Called “War is the H-word”) Leela disguises herself as a man to join the army to keep an eye on Fry and Bender (who joined the army to get a discount on gum.)
Ham-flavored gum.
Lassie was always played by a male collie.
in splash, when daryl. hannah walks into the department store, an employee says something about her “annie hall” look. so perhaps annie hall should be added, what with diane keaton’s predilection for men’s suits?
jwbates-
Yes, ham-flavored gum. To give you “breath as fresh as a spring ham.” And thanks for pointing out Lassie.
jenny-
Good point. I hadn’t remembered that line. (Haven’t actually seen Annie Hall, either.) The line I remembered was something like “a pretty girl like you shouldn’t be wearing boxer shorts.”