The Autodidact’s Bookshelf: Breaking Down Sex Differences With Gender-Bending Characters

Stories about reversed gender roles reveal how love can transcend sex and that some aspects of gender are merely performative

As the male “Cesario,” Viola is able to have a deeper relationship with Orsino. Image Credit: Frederick Richard Pickersgill (English, 1820-1900), “Orsino and Viola”/Wikimedia Commons

A lot has changed for girls since I was growing up in the 1980s. It is striking, for example, the number of female lead characters in contemporary children’s movies. Moana, Mulan, and Anna and Elsa from “Frozen” are some of the most famous and best-loved Disney protagonists today. My young son and daughter will probably never think twice about seeing female lead characters.

Nevertheless, women face many challenges today, even in the fantasy reality of film. In “Mulan,” for example, women aren’t allowed to join the military, so the central character cuts her hair short and dresses up as a boy to take the place of her father, who has been drafted in the Chinese army but is too elderly to serve. As a woman, Mulan is a disappointment—she makes for a lousy housewife. But in her role as a man she turns out to be a savvy warrior, and her quick wit helps save the kingdom from an invasion by the Huns.

“Mulan” reminds us of the strict rules that society often prescribes around activities based on gender. Another example comes from “National Velvet,” in which the 12-year-old Velvet Brown dresses up as a boy to win the Grand National horse racing championship. She has to pretend to be a boy because the rules won’t allow girls to compete as jockeys. Similarly, in Virginia Woolf’s “Orlando: A Biography,” an English nobleman obtains eternal youth and lives 300 years in English high society, first as a man and then transformed into a woman. Orlando learns the hard way that many rights, including owning property, have not been available to women through the ages.

Gender and Romance

While dressing as men allows these fictional women to experience more freedom, it can also give rise to romantic complications. In Shakespeare’s “Twelfth Night,” for example, a shipwrecked Viola disguises herself as a man named Cesario when she finds herself alone in a strange country. Thinking her twin brother, Sebastian, to be drowned at sea, she becomes a servant to Duke Orsino and falls in love with him. Of course, Orsino thinks Cesario is a man, and besides, he is already in love with Olivia, a beautiful maiden who is mourning the death of her own brother and has sworn off romance.

Viola, dressed as Cesario, acts as an intermediary between Orsino and Olivia, hoping to win the latter’s favor for the duke. But Olivia falls in love with Cesario instead, forming a bizarre love triangle. Complicating matters further, Sebastian eventually reappears, and Olivia confuses him with Cesario because of their similar appearances.

“Twelfth Night” is a romantic comedy, but it holds some deeper lessons. One is that we often hide our feelings for other people, so the object of our affection is kept in the dark. Sometimes, as with Orsino when he learns Cesario is really a woman, the feelings are requited when they come to light. But this reciprocity is far from assured, and the vulnerability of loving someone out in the open explains why so many keep their feelings secret.

Overcoming Gender Barriers

Next, consider the 1982 film “Tootsie,” starring Dustin Hoffman, in which an unemployed actor develops a bad reputation around New York and can’t find work. Out of desperation, he dresses up as a woman to audition for otherwise unavailable jobs. After landing a spot on a soap opera, Hoffman’s character, Michael, forms a close bond with a co-star, Julie, who is tricked into thinking he is actually “Dorothy.” Michael falls in love, but to Julie it’s merely a dear friendship. Eventually the truth comes out, as both Michael’s gender and his true feelings are revealed. Julie gets over her sense of betrayal, and the movie leaves open the possibility that she and Michael will end up together.

One of the more touching aspects of “Tootsie” is the way Michael comes to better appreciate women while dressing in drag. Before he became Dorothy, Michael was an insensitive guy who saw women as sex objects. That changes when he experiences life as a woman firsthand. Sometimes his escapades are humorous: Michael takes a genuine interest in ladies’ fashion and beauty practices. But when a fellow actor tries to force himself on “Dorothy,” Michael realizes that there is a darker side to women’s realities too.

Image Credit: Wikimedia Commons

In “Tootsie,” Julie can’t see past the gender barrier. It acts as an impediment to any sensual feelings she might have for Dorothy. But this isn’t always the case in film. In the 1992 movie “The Crying Game,” an Irish Republican Army member named Fergus develops romantic feelings for Dil, the former love interest of an IRA hostage whom Fergus befriended but who died in a botched hostage-swapping scheme. Dil turns out to be transgender, which at first shocks and repulses Fergus, but he overcomes this reaction and an attraction remains.

“The Crying Game” demonstrates the importance of first impressions. Fergus is perhaps able to look past the gender issue with Dil because he has already developed feelings for her as a person, and those feelings even have a sensual component because he initially thought of Dil as a woman. Thus, while Dil’s gender comes as a shock to Fergus, he is still drawn to her.

This stands in stark contrast with Julie’s experience in “Tootsie,” in which she initially sees her relationship with Dorothy as platonic. Also important is that Dil reciprocates Fergus’ feelings, unlike, say, Viola in “Twelfth Night,” who resists the advances of Olivia because she is in love with Orsino.

Gender has become a hot-button issue in politics in recent years, with debates arising about which bathrooms transgender individuals should use or which sports teams they should be allowed to compete on. Historically, society has taught us to see in the binary terms of male or female. But literature and film teach us that we are capable of taking on a multitude of character traits, which can be associated with either sex. Gender is about more than organs; it’s also a role each one of us acts out in the drama called life. Most importantly, behind the gender there is always a unique person, both capable of love and wanting to be loved.


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