Habiliments and Humor: How Hollywood Broaches the Topic of Cross-Dressing in Comedic Stories


“The clothes make the man” the old expression goes. But which clothes are we talking about? If you’re a fan of comedy- theater, television, and film- you’ve undoubtedly seen many stories where cross-dressing is the theme (or at least one of the themes).

In ancient Greek mythology, Hercules/Heracles wears a dress when Omphale enslaves him. Achilles puts on women’s clothing his mother Thetis gives him, Athena aids people in the guise of a man, Tiresias turns into a woman after angering Hera, and worshipers in the cult of Aphroditus put on women’s apparel. In Norse mythology, Thor and Odin also occasionally cross-dress.

During the 20th century, various films about men disguising themselves as women were produced. Billy Wilder’s 1959 crime comedy, Some Like It Hot, stars Tony Curtis and Jack Lemmon as Jack and Jerry (respectively), two 1920s prohibition-era jazz musicians who dress up as flapper girls and go on the run from Chicago after witnessing the St. Valentine’s Day Massacre. They travel to Florida where they meet stunning ukelele player/singer, Sugar “Kane” Kowalczyk (Marilyn Monroe). Things as you imagine get silly and awkward. But, in the end, “nobody’s perfect,” states one of the characters.

In Tootsie, Michael Dorsey (Dustin Hoffman) masquerades as “Dorothy Michaels” to get an acting gig in New York City. In Mrs. Doubtfire, Daniel Hillard (Robin Williams)- recently divorced- becomes the titular housekeeper to continue seeing his children.

Other films you may be familiar with include The Rocky Horror Picture Show and To Wong Foo, Thanks for Everything! Julie Newmar. More serious flicks like Boys Don’t Cry and Dallas Buyers Club have also dealt with the subject.

The topic of gender/gender identity has been a major one in the past 8-10 years! It’s important though to make a few distinctions. Sex is different from gender, orientation is different from gender, and gender is different from how one dresses. They all may overlap (and frequently do), but as categories, they are all each separate. Sex is the “equipment” for lack of better words. Sex is the reproductive anatomy that people are born with, and it is universally binary amongst all animals.

Gender is close to sex but not the same thing. We have the traditional model of masculine and feminine genders (fueled hormonally by testosterone and estrogen, respectively). Usually, masculinity accompanies males and femininity accompanies females. But not always (which is why we have the terms “cis gender” and “transgender”).

Sexual orientation is the attraction one may or may not feel for someone else. How many orientations are there? You can be attracted to someone of the other sex (heterosexuality), the same sex (homosexuality/lesbianism), or both (bisexuality). You can also feel attraction for neither (asexuality), and the gender of the person may vary. But- generally speaking- there are three orientations. What about people who are attracted to themselves, inanimate objects, or abstract qualities (sapiosexuals, e.g.)? Or- in the case of more disturbing circumstances- animals and/or children? Do those orientations count as well? Possibly.

And then how one dresses is the fourth category. It is arguably the least rigid and most fluid category of all four. Men will usually wear suits and ties and tuxedos and wing-tip shoes. Women will usually wear dresses, skirts, and stilettos, but neither respectively needs to. Films like Mrs. Doubtfire and Some Like It Hot make the practice of doing so ironic. Movie-goers certainly got a kick out of movies like these when they were initially released. But could they be released today, or would people pan them as tasteless and offensive? Today’s zeitgeist is much different. It’s worth considering, though, when consuming any work of comedic art where the butt of the jokes lies.  

First let’s jump way back in time and look at some Shakespearean comedies. One of Shakespeare’s trademarks was to have female characters (always played by male actors at the time) masquerade as men. The two most prominent plays to do so were As You Like It and Twelfth Night. In As You Like It, Rosalind, who is in love with Orlando, is exiled to the fictional Forest of Ardenne. She dresses up in a jerkin and doublet, breeches, and a cap. Rosalind then adopts the alias “Ganymede” (named for Zeus’s cupbearer).  Her cousin Celia dons men’s apparel as well, adopts the alias “Aliena,” and accompanies her “cousin” to Ardenne. Together they encounter various people who they dispense romantic advice to. These include lovesick shepherds and other country-dwellers.

Something similar occurs in Twelfth Night. Viola and her brother Sebastian are shipwrecked on the island of Illyria. Viola disguises herself as a young man named Caesario. She falls in love with Duke Orsino, under whose service she enters. However, Olivia, the young woman whom Orsino loves, falls in love with “Caesario.” This occurs when Orsino has “Caesario” act as his intermediary.

In both Shakespearean productions, the joke is at the confusing sets of circumstances and incidents of mistaken identities that arise. All are neatly and happily resolved. Elizabethan gender codes were of course far stricter than any modern or even Victorian codes. Anything that fell outside them was treated severely. Shakespeare, though, had the unique ability to both adhere to and inventively diverge from those codes. He could do so without losing the queen’s good graces or finding his head on a chopping block.

Imagine yourself as a 16th century Globe Theater attendee. You would see a male actor dressing up as a female character. This female character dresses up as a male persona and pursues a male character. Along the way “he” catches the heart of another young woman (also played by a male actor). As you can see, it gets complicated very fast, and that “delightful confusion” (if you will) is the whole point! Did people struggle as much with gender identity and orientation at that time as people do now? Absolutely. Shakespeare approached the issue(s) in a manner that was very open and forward-thinking for its time, though. His comedies were commentaries on the complex nature of love, sex, and gender. As You Like It and Twelfth Night were not works of cruel, outright mockery!

Now flash-forward- Some Like It Hot…Tootsie…Mrs. Doubtfire. In each of these films the men who disguise themselves as women do so for very specific reasons. Jack and Jerry do so to avoid the mob. Michael Dorsey does so to land an acting gig. Daniel Hillard does so to continue seeing his children. Jerry and Jack, Michael Dorsey, and Daniel Hillard are all traditional male personas. When they put on a wig and a dress, the world doesn’t see them as men in drags. People don’t stop and stare, point and laugh, scowl, verbally jeer, or physically assault them. People believe they really are women.

The humor comes from its dramatic irony. The men in disguise are heterosexual and have traditional masculine temperaments. Confusing situations arise when other men pursue them, or they are smitten with women. They must keep their “real” identities secret for practical reasons, not for fear of bigotry, violence, or backlash. If the latter were true, it would be perfectly reasonable to decry them as tasteless and offensive. But in each film a more positive message emerges. Some Like It Hot toys around with the nature of marriage and relationships. Tootsie‘s “Dorothy Michaels” becomes a pro-feminist icon of the early 1980s. Mrs. Doubtfire addresses the knotty situation kids face when their parents get divorced. But Robin William’s character demonstrates that parents’ love for their children is unconditional.

Stories about or involving cross-dressing have long been a staple of theater and Hollywood. Hopefully the comedic ones we’ve seen know how to balance that line between humanity and humor. They can explore the complexity of people with taste and insight. Consider William Shakespeare’s Twelfth Night and As You Like It. You can also check out Billy Wilder’s Some Like It Hot, Sydney Pollack’s Tootsie, or Chris Columbus’s Mrs. Doubtfire. All of these plays and movies balance that line successfully.

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