You’ve seen the movies, you’ve read the books; cross-dressing is a common theme in fiction. It’s in mythology, history, folklore, literature, operas, plays, movies, television, and even music. Most importantly though, it has caught the attention of the alternative and dare I say? nerdy aspects in the pop-culture experience that we call life.
There are a few different kinds of plot points based on cross dressing. A very popular one, especially by those such as Shakespeare is one I like to call: Girls in Caps and Trousers. Women dressing as men have been both a cultural and historical phenomena. Some are trying to find their lost loves, some to fight in a war, and some just want the same privileges and opportunities their brothers get. Since there are many of examples of this particular trope (Japanese anime has hundreds of them) I will stick to only a couple.
Disney’s Mulan is an example that many people would think of first. Due to the illness and general advanced age of her father, Mulan steals his armor, cuts her hair, and joins the army to fulfill the household quo. She goes through many hardships including discovery, but eventually she saves the day and is rewarded with a hot general (whose life she saves more than once).This is one of few movies (especially for Disney) that had a female protagonist actually makes things happen in her life instead of just reacting to things that happen to her. What is particularly interesting about this is that it does not end with a wedding. It ends with her family being proud of her, and the joy of her returning home safe and sound. The best part is that it is (loosely) based on a true story.
Women wanting to join the army is a surprisingly (at least to me) common reason for cross dressing. In one episode of Futurama, “War is the H-word”, Earth is at war and women are banned from joining the service due to Captain Zapp Brannigan being a sexist pig of a man. Determined to prove her worth and to keep Fry and Bender from getting killed, Leela disguises herself as a man called Lee Lemon. Of course Leela quickly proves to be the best soldier of her unit and quickly catches the eye of Brannigan. Brannigan is soon filled with hope (plus some other emotions which are weird and deeply confusing). Eventually, Leela does help save Fry and Bender from destruction and Brannigan (with a deep sigh of relief) finds out her identity and has never been so happy to be beaten by a woman; to which Leela replies “Let’s do it again sometime” before taking off in a helicopter, totally badass as usual.
In Tolkien’s The Lord of the Rings: Return of The King, Éowyn disguises herself as man and calls herself Dernhelm. During the battle of the Pelennor Fields, she confronts the Witch-king of Angmar, Lord of the Nazgûl. The Witch-king threatens to “bear you away to the houses of lamentation, beyond all darkness, where your flesh shall be devoured, and your shriveled mind be left naked to the Lidless Eye.” (A fairly decent threat to use next time someone pisses you off.) Arrogant due to the 1,000-year-old prophecy by the Elf-lord Glorfindel, which says that the Witch-king would not fall “by the hand of man,” The Witch-king further boasted that “no living man may hinder me.” Éowyn then vanquished him awesomely. This proves that time and time again that there is always a loophole in every contract and a trick in every prophecy.
These ladies made convincing enough men for their noble purposes, but what about the other side? Cross-dressing males are used a bit differently in literature. While females dressed as males can be seen in both comedy and tragedy, cross dressing men are predominantly there for comedic effect. This one I like to call: The Skirt with a Five o’clock Shadow.
Bugs Bunny is one of the first cross-dressers I’d ever seen. Often the audience would see this wascally wabbit dressed to basically seduce Elmer Fudd or whoever else was the antagonist of that particular cartoon. These guys would buy it hook, line, and sinker, and usually only the reveal of ears or a tail would give Bugs away. And what can I say? He was pretty hot. Why Bugs did this is a bit of a mystery (at least at times), sometimes it was to humiliate the antagonist, to convince them of something, or for kicks and giggles. For a cartoon, it’s a strangely adult theme. This is a reminder to the days where cartoons were not necessarily just for children and were first just something to distract everyone before the movie. Cross-dressing is still a surprisingly common thing to see in cartoons even today.
Another is The Monty Python troupe. They have been known to cross dress for comedic purposes in both their TV series and films. They usually dress up as older, unattractive ladies referred to as “pepperpots”. These ladies were some of the funniest characters, mostly because they were crotchety old ladies and middle-aged mums willing to speak their minds. Unlike Bugs Bunny they were not attractive. The only recurring attractive woman of their troupe was hardly ever used or given any lines; in fact most people don’t even remember her name (Carol Cleveland). I suppose a man in drag will win over an attractive woman (at least when it comes to comedy, sadly).
And last is: My Clothes Don’t Necessarily Define My Gender or My Sexuality. This last one may be a bit controversial. Most of my examples are male because woman in this day and age can wear pants without there being a national crisis. Males do not have this particular privilege. Don’t worry; they have almost all the others.
Sailor Moon’s Haruka Tenoh (Sailor Uranus) in both the “Sailor Moon S” and “Sailor Stars” seasons wears boys’ clothes most of the time. She even wears the boys’ uniform to school. She is very masculine, to the point of being mistaken for a boy by other characters on more than one occasion. Don’t worry though; she wears a miniskirt along with the other sailor scouts when she has to. I bet she would prefer to wear something like Tuxedo Mask, but she didn’t get to choose the uniform. She mainly fights alongside her partner (and lover) Michiru Kaioh aka Sailor Neptune, a very elegant “princess-like” girl.
Another that many of you might remember is the infamous HIM from the Powerpuff Girls series. He is shown wearing a skirt, fishnet stockings, and high heel boots lounging on his red couch. HIM’s voice is unusually a high-pitched falsetto, but quickly becomes a deep growling bass when enraged. Despite his flamboyant appearance HIM is often considered the most evil of all the Powerpuff Girls’ villains (and likely represents Satan). He is smart, stylish, organized, hypnotic, and manipulative he is also a shape shifter and has many demonic forms. HIM came the closest of all the villains in defeating the girls. HIM is a truly sinister man-lobster-lady-demon…thing.
HIM puts me in mind of The Rocky Horror Picture Show. More specifically, of Tim Curry as Dr. Frank N Furter, a “sweet transvestite from transsexual Transylvania.” (Actually, he is an alien with an appetite for sex from either sex, although he appears to specifically enjoy blond-haired, tan, muscle men, due to the effort he put into creating one for his own personal use (Rocky). This sparked one of the weirdest weddings ever enacted in cinema, and possibly one of the first featuring a gay couple. After which Dr. Frank N Furter seduces everybody, then everybody seduces everybody else, and there is singing and some murder thrown in for good measure. It’s a camptastic movie. Perhaps not the best one to represent transsexuals, but no one said it was a documentary.
What is it about cross-dressing that people find so interesting? Is it the mystery, the suspense? Is it even perhaps the act of becoming something completely opposite of how society has defined your gender? What would happen if for one day you lived as the opposite sex? How would you feel? What if you were discovered? What would you do? Have you ever cross-dressed? Tell us about your thoughts and experiences in the comments below!