To answer this question, it’s best to start by defining terms. “Trans” most generally indicates a gender identity that differs from one’s biological sex. In binary terms: a biological male who identifies as female (trans woman) or a biological female who identifies as male (trans man). (Those who do identify their gender as in alignment with their sex are called “cis” or “cisgendered.”) More generally, “trans” can be used to refer to those who are gender non-conforming, identifying as neither male nor female, neither normatively masculine nor normatively feminine. A few other terms that serve as synonyms for this broader sense of trans include “genderqueer” or “enby” (n.b. or non-binary). Also key to this definition is that it does not (necessarily) speak to sexuality, for gender identity is separate from sexual orientation. Of course, definitions and discussions of the word and concept “trans” are deeper and more complex than this brief overview suggests, but it suffices to allow me to address the question of trans representation in Classic Hollywood.
To answer the question directly, I would have to say “Perhaps.” Classic Hollywood does offer characters we can interpret as trans today, but only in retrospect. Today’s “out” trans characters often share their history and foreground identity issues, such as Sophia Burset (played by trans actress Laverne Cox) in Orange is the New Black (2013-) or Maura Pfefferman (played by cis male actor Jeffrey Tambor) in Transparent (2014). By contrast, in an era before the term was used and alternate gender identity displayed in any form was deemed illegal, immoral, or neurotic, trans identity must be interpreted through subtle aspects of character appearance, behavior, and interactions.
Reading retroactively, then, do we want to consider Marlene Dietrich in a tuxedo in Morocco (1930) as a trans character, where the purpose of blending genders or dressing as the “opposite” sex is not presented outwardly as feeling that her gender identity differs from or opposes her biological sex? Mademoiselle Amy Jolly certainly can be read as trans, since we do not have backstory to explain how she feels about her/their gender beyond the confines of a stage act and the troubled heteronormative romance at the heart of the film. To read Dietrich’s character as trans, we would argue that her desire for men is about stability and fulfilling social norms, and that she is happier and more confident on stage, where she can perform a more complex gender (and sexual) identity.
By comparison, I would decidedly not read as trans Cary Grant’s David in Bringing Up Baby (1938). In the scene in which his clothes are whisked away by Katharine Hepburn’s Susan while he showers, his crossdressing is about her attempt to keep him from leaving her. In a pink, frilly robe, he is confronted by Susan’s Aunt Elizabeth (May Robson), who asks why he is wearing it. He explains, “Because I just went gay all of a sudden!” Here, we have at best a subversively queer moment and at worst homophobia via the conflation of crossdressing and homosexuality in men. We have even less of a suggestion of intentional gender nonconformity for personal pleasure than in Morocco.
To my mind, the most persuasive example of a character that a contemporary audience might call trans is Katharine Hepburn’s lead roleas the titular character in Sylvia Scarlett(1935). Working backwards from reception to production, we learn that the film was panned at its opening. Gay “woman’s director” George Cukor even attempted to have the film shelved after a disastrous test screening. And it was one of the performances that temporarily identified Hepburn as “box office poison.” Despite its cult status today, Cukor went so far as to declare Sylvia Scarlett a sharp, painful lesson to him as a young Hollywood director. As quoted in Queer Cinema, The Reader, he stated, “I wasn’t going to be so goddamned daring after [making Sylvia Scarlett]. I thought, ‘Well, kiddo, don’t you break all sorts of new paths, you just watch it.’”
Exactly what “new paths” this film forges relate to its plot as well as its main characters. Sylvia Scarlett is based on a 1914 novel by Compton MacKenzie. Within this two-volume Bildungsroman, one small section features Sylvia deciding to disguise herself as Sylvester to see what living as a man is like. Eventually, she gives up the practice, which is depicted as one of many adventures. Cukor enjoyed the novel and the premise of this specific section, but he was advised to create a reason for Sylvia’s crossdressing. The film became a tale of a young woman who flees after her mother’s death in the guise of a young man to go off with her gambler father (Edmund Gwenn) who is fleeing those from whom he has stolen money. Sylvia declares in the opening scene that she must become Sylvester—tough, hard and masculine—so she will cause her father no worry. Then she ruthlessly cuts off her long braids. Soon after, father and “son” end up part of a group of con artists-cum-stage performers.
By giving the character a reason to dress as a man, the film disallows the possibility that she is experimenting with gender, seeking a fitting or fluid identity. However, in the course of the film, Sylvester finds increasing pleasure in masculinity as he experiences it. He feels freer to express his views and to desire others, shifting from introverted female to extroverted male.
Others’ responses to Sylvester further an interpretation of the character as trans. No one within the narrative suspects him of “really” being a woman, for example. A few tense moments force Sylvester to contemplate the meaning of his gender (and sexuality), such as when the troupe’s female member, Maudie (Dennie Moore), draws a moustache on his youthful, hairless face and kisses him passionately. The scene features a very obvious cut to shorten the kiss, followed by Sylvester pushing her away, disgusted, at least in part because there is an intimate relationship between Maudie and his father.
The relationship that leads most to a reading of Sylvia/Sylvester as trans rather than as a woman in drag is the friendship that becomes love with Michael Fane (Brian Aherne). Fane is a handsome young bohemian painter in a stormy relationship with a Russian ex-patriate noblewoman (Natalie Paley) and acts the part of the playboy. But when he meets Sylvester, he experiences an attraction he cannot name. When he feels he has figured it out, he asserts, “I say! I know what it is that gives me a queer feeling when I look at you!” He concludes that it is the desire to pain Sylvester’s portrait.
In trans terms, I would argue that Fane’s attraction is not gay but more generally queer (or contra-straight): it is precisely Sylvester-as-trans that draws him. This is validated when Sylvester steals a dress and comes to Fane in feminine persona to declare her affection. She is at turns too aggressive and then too falsely coy to interest him in anything other than laughing at her. We see that gender is a performance and Sylvia is out of practice. If Sylvia/Sylvester is trans, then we might posit transphobia if the pair’s relationship ended here.
By contrast, Monkley (Cary Grant), for example, is fine bunking with Sylvester as a “proper little hot water bottle” early in the film, but thrilled to find out she is “really” Sylvia, to whom he promptly proposes a life together even though he desires Fane’s disenchanted Russian princess more. If he cannot have the upper-class feminine prize, he will enjoy someone whose gender reveals to him a better con than even he is capable of.
The film ends, however, with Fane and Sylvia/Sylvester together. Not entirely the young man of most of the film, the character who escapes with Fane by train is a gender-ambiguous creature in a topcoat. This non-binary or genderqueer person is what draws Fane and creates the happily-ever-after ending.
I realize that it may be easiest to call Hepburn’s character and the whole film a “queer” romp without specifying trans identity. However, as such terms offer more specific interpretations of how we “do” gender in contemporary America, exploring Sylvia Scarlett or even Morocco as films about trans experience provides a compelling way to read and validate representations of gender-nonconforming identities in films of the past.