In this biweekly column, Michael Koresky looks back through a century of cinema for traces of queerness, whether in plain sight or under the surface. Read the introductory essay.

Katharine Hepburn and Cary Grant in Sylvia Scarlett (George Cukor, 1936)

Few movie subgenres fit as naturally yet uneasily into the queer canon as the cross-dressing farce. While it’s difficult to envision the span of even a loosely defined gay cinema without such altogether wonderful comedies as Some Like It Hot, Tootsie, and Victor/Victoria, or Barbra Streisand’s musical melodrama Yentl, each of these films distinctly posits the choice of the main characters to don the disguise of the “opposite” gender as one of desperate necessity, whether for reasons of professional gain or life-or-death well-being. And while the films listed above—and even some less reputable stalwarts of the genre, like Lisa Gottlieb’s delightful Just One of the Guys and the Wayanses’ somewhat creepy White Chicks—are sophisticated enough to gesture at the idea that the lessons the characters learned while performing their charade have forced them to question their entrenched beliefs about gender and their own selves (Some Like It Hot is still, surprisingly, the most genuinely anarchic when it comes to this) there’s never the sense that they are ultimately assuming or coming into their own identities. Taking a page out of Shakespeare’s Twelfth Night, by film’s end, all is revealed and gender balance is restored, the “bending” of gender a necessary step on the road toward heterosexual fulfillment.

Cross-dressing is such a convention of American comedy—and as such so utterly conventional—that it’s amusing to consider how distasteful the concept can be to viewers when it deviates from the playbook. A prime progenitor of these films, George Cukor’s Sylvia Scarlett, in which Katharine Hepburn disguises herself as a young boy to evade authorities and cross the French-British border with her embezzler father, angered audiences in 1935, presumably in part for its lack of moral editorializing. It would for decades be remembered first and foremost as a notorious flop, losing RKO $363,000 (an enormous sum at the time); forever souring the relationship between Cukor and the studio, who never worked together again; and nearly killing Hepburn’s career at what appeared to be its peak. It would take five years and the comeback of Cukor’s The Philadelphia Story to cement her reputation again and for people to rid themselves of the distasteful image of Hepburn looking quite comfortable in boy clothes and being chastely pursued by both men and women.

All these decades later, the discomforts of Sylvia Scarlett are precisely what have given the film its longevity as an object of curiosity and affection. It’s an exceedingly queer movie, tonally schizoid and burdened with an emotionally zigzagging plot that seems content to give you barely enough psychological information about each character before they’re acting in a way you never could have expected and thus transforming the narrative over and over. That the film begins as something like a prestige costume melodrama before sojourning in the realm of poetic realism then diving back into screwball comedy before submerging itself abruptly into tragedy and going back to farce surely must result from the realities of its screenwriting travails.

To adapt Compton Mackenzie’s 1918 The Early Life and Adventures of Sylvia Scarlett, a longtime favorite novel of his, Cukor hired short-story writer John Collier, who might be best known to a certain kind of queer—namely, this one—for his supremely unsettling horror story “Evening Primrose,” which would, unfathomably, become the inspiration for a late ’60s Stephen Sondheim made-for-television musical with Anthony Perkins (read more about that bizarre and beautiful buried treasure in an article I wrote for the March-April 2018 issue of Film Comment). Collier, whose stories tended towards the macabre and unconventional, wanted to begin the film in medias res, with Hepburn already in boy drag, and force viewers to work their way through the narrative. This and other ideas made the studio suspicious, so Cukor added two Hollywood screenwriters—the chewily named pair of Gladys Unger and Mortimer Offner—to the mix, who added the film’s corny prologue and a somewhat baffling new ending, which, in its final version, communicates mostly the sense that the filmmakers have thrown up their hands. At the same time, the anything-goes, patchwork quality of the film is entirely in keeping with the devil-may-care attitude of the protagonist, a woman who does what she wants when she wants and deals with the consequences later.

The film that best and most explicitly exploits her appealing androgyny, Sylvia Scarlett allows Hepburn to be one of her best selves. It’s clear that Sylvia—and Hepburn—enjoys being a boy. Her willowy alter ego Sylvester Scarlett is playful and physical, with a Peter Pan–ish quality: in one scene, he leaps out of a bedroom window in one smooth, dance-like self-defenestration that has an Errol Flynn balleticism. In what was probably intended as a backhanded compliment, Time magazine wrote that the film “reveals the interesting fact that Katharine Hepburn is better looking as a boy than as a woman.” Indeed, Hepburn borders on Leo DiCaprio–dreamy as Sylvester, her short, previously braided hair attractively brushed and parted to the right, angular features giving her a masculine boldness even as she looks childlike and diminutive alongside the film’s two strapping men: Cary Grant as Cockney swindler Jimmy and Brian Aherne as sensitive painter Michael. The attractive but untrustworthy Jimmy has taken Sylvia and her father (Edmund Gwenn), recent runaways from Marseille, under his wing, first as cohorts in a series of scams around Victorian London, then as partners in a troupe of traveling players called The Pink Pierrots, which also includes Maudie, a daffy Buckingham Street housemaid, played by Dennie Moore, who has accompanied these three bounders on their adventures. Local artist Michael comes to one of their shows and is instantly intrigued by young Sylvester: “I like you . . . Come up to my studio.” It’s because of, not despite, Hepburn’s boyishness that Michael feels an attraction. “There’s something about you…” he muses, while Hepburn stretches out on the gymnast rings that suggestively dangle in his studio. She demurs, not ready to reveal herself to him yet.

By this point, Hepburn has already tied herself in knots trying to evade the desire of others and suppress her own. Two of the spiciest moments take place in the highly suggestive back-door spaces of the troupe’s caravan. In the first, Maudie touches Sylvester’s face, inspecting it for whiskers; with nothing to be found she paints a pencil-thin Ronald Colman mustache on her face. So instantly dashing is Sylvia that she plants a kiss flush on her mouth. This reportedly elicited groans from test audiences and resulted in mass walkouts. After Sylvia pulls away, a quick wipe transition—conspicuously the only one in the film—cuts in the middle of their conversation and takes us to a moment just minutes later, Hepburn in a different position in the room. Whatever was trimmed, it’s clear that the movie wanted to get out of there faster than even Sylvia. But things aren’t potentially much better when she returns to bunkmate Jimmy’s room. In the foreground, Grant starts unbuttoning his shirt, and sure enough, in a reveal Clark Gable would have been proud of (It Happened One Night’s “walls of Jericho” came down, of course, just one year earlier), there’s nothing underneath but a beckoning bare chest. Suddenly shy Sylvia, for fear of her own desire getting the best of her, turns away, though Jimmy insists that he and the boy sleep in the same bed: “You’ll make a proper hot water bottle.”

Jimmy’s come-ons are less outwardly sexual, however, than those of Michael, whose continued astonishment at his own attraction to the boy finds its best expression when he says, “I know what it is that gives me a queer feeling when I look at you . . . There’s something in you to be painted.” Thus established as an androgyne muse, Sylvia must begin to truly reckon with her feelings for the handsome bon vivant. As if things needed to be further complicated, Michael’s mistress Lily, a Russian adventuress played by Natalie Paley—the actress an actual descendant of the Romanov family and a first cousin of Alexander II—arrives at the house and is also taken with Sylvester, calling him “such a pretty boy.” Later, upon discovering that she is a woman, she declares seductively “how charming” and kisses her on the cheek. The reveal is even more exciting, however, for Michael; when Sylvia puts on a borrowed dress, he finally feels justified in his uncomfortable arousal around the boy, and as a result cannot stop laughing jovially. For the audience, however, seeing Sylvia in a summery dress again might cause distress, shattering the romance completely—what is meant to be right suddenly looks so wrong. Witnessing Hepburn reclaim her femininity, I could think of nothing other than Greta Garbo’s apocryphal cry “Give me back my beast!” upon seeing Jean Marais’s transformation back to princely human at the end of Jean Cocteau’s Beauty and the Beast.

With such mild ribaldry, one wonders what Sylvia Scarlett may have looked like just a few years earlier, before the Hays Code was instituted and forever changed American movies. Hepburn doesn’t have the self-possession of Dietrich, the romantic loneliness of Garbo, or the fuck-it-all sass of Mae West; her onscreen confidence was often productively undercut by an acute, self-conscious neurosis that made her a more apt post-Code star than any of those women ever might have been. Cukor, whose own open-secret gayness is hardly incidental to any discussion of the gender playfulness of Sylvia Scarlett, is credited as being Hepburn’s discoverer and early champion, convinced there was something special in her even after she screwed up a screen-test for his A Bill of Divorcement (1932), which would be her first role and the first of 10 movies they made together.

It’s Hepburn, and the clear delight she takes in enacting her charade, that gives Sylvia Scarlett its real charge. In the head-spinning last half-hour, there’s no lingering doubt that “normal” love has prevailed, as the plot hastens to establish two separate heterosexual couples—albeit ones with varying degrees of health and happiness. Yet if there’s a bitter taste left by this triumph, it might be because all relationships in his film are, in one way or another, con games. Grant’s virile crook and Gwenn’s unprincipled father are just the most blatant of the film’s ethically dubious players; Michael and Lily mostly operate on self-interest and opportunism, and more than one romantic matchup in the film ends up in attempted or actual suicide.

Sylvia Scarlett may chart the contours of various romances, but there’s a grimness at its core. “You’ve got the mind of a pig,” Sylvia at one point says to Jimmy, to which he replies, “It’s a pig’s world.” So even if Cukor’s film falls in line with the conventions of cross-dressing farces in upholding the social status quo, in its productive screwball cynicism it finds ways to radically invalidate itself. This makes Sylvia Scarlett’s initial commercial and critical failure feel right: it was never destined to be easily loved.

Michael Koresky is a writer, editor, and filmmaker in Brooklyn. He is cofounder and editor of the online film magazine Reverse Shot, a publication of Museum of the Moving Image; a regular contributor to the Criterion Collection and Film Comment, where he writes the biweekly column Queer and Now and Then; and the author of Terence Davies, published by University of Illinois Press, 2014.