While it may be surprising to consider any of them being associated with a failure, there was a time in which George Cukor, Katharine Hepburn and Cary Grant were considered slightly controversial figures within Hollywood, with Hepburn, in particular, having to endure allegations of being “box office poison” for several years in the 1930s after a run of poorly-received films that supposed portrayed her as an unfavourable, failed star whose popularity declined faster than that of any of her contemporaries, and would only start to recover when reuniting with Grant and Cukor a few years later, with the combination of Holiday and Bringing Up Baby is the start of a career revival that reached its apex with The Philadelphia Story a couple of years later. However, we shouldn’t only look at the consolidated successes from this time, since giving some time to the supposed failures is also a fascinating endeavour since it gives us insights into why Hepburn lost favour so quickly with critics and general audiences. The most notorious film in which she starred during this period was Sylvia Scarlett, which was adapted from the novel The Early Life and Adventures of Sylvia Scarlett by master of wit Compton Mackenzie, which is a gender-bending satire based around a father-daughter team of con artists, with the daughter masquerading as a man to take advantage of their victims, who were far more trusting of a rebellious young boy than a manipulative woman. To be clear, every bit of disdain felt towards Sylvia Scarlett at the time was entirely unearned, and quite simply the result of this film being made for an audience that could not appreciate its nuances. A witty, charming and freewheeling cinema by one of the great directors of his era, Sylvia Scarlett is a triumph, and one that has more than earned the right to a critical re-evaluation, for several reasons that we can find liberally scattered throughout this film.

There are many reasons why audiences were not receptive to this film when it was released, even for decades afterwards it was shrouded in obscurity and controversy, only recently being reconsidered as an unpraised masterwork. The reality that we need to introduce is quite simply that Sylvia Scarlett was too ahead of its time for audiences when it was released. This is a film that has attained its most effusive praise and ferocious support within the queer community, who view this film and its original novel as being an accidental queer text, an exploration of the art of drag performance long before it was part of the mainstream. While it is unlikely that the film was underwhelming as a result of its subject matter (after all, the works of William Shakespeare have been omnipotent in terms of how gender is portrayed, both directly and through mere allusion), it likely did have some factor, even if the film was not ever once promoted as being even vaguely a queer statement, despite being claimed by the community. The reasons for this are not unclear, since any work that is going to take an approach in which gender identity is part of the plot is immediately going to draw our attention, especially in a more modern, tolerant society where discussions around identity are not nearly as controversial as they may have been in 1935. We are never entirely sure whether the characters in the film are aware of how they are being reanalysed through a queer lens, but with an openly gay director at the helm, as well as two actors leading the film who faced questions of their sexuality over the years, it would be foolish to entirely ignore the queer underpinnings that drive this film, since there is some merit in recontextualizing Sylvia Scarlett as a comedic piece that has very clear resonance within those members of the community that have found liberation outside of the binary, and who embrace the refusal to conform to a single gender identity, a theme that is profoundly modern, but yet woven so deeply into the fabric of this film.

On the subject of what makes the film successful, the primary source of both the praise and criticism that has been heaped onto Sylvia Scarlett is directly related to the performances that sit right at the heart of the film, with some viewing them as awfully over-the-top, while others look at them as ingenious, subversive efforts by some of the most exceptional actors of their generation. Much like the plot, it is clear that audiences simply did not appreciate the nuances of the work being done by these actors at the time, since the entire cast is uniformly quite brilliant, turning in work that may not be formally their best performances, but rather serve to be as playful and freewheeling as the film that surrounds them. Katharine Hepburn is the main attraction, and this was one of the first times she took advantage of her gamin appearance to play a character that veered towards the masculine. It was integral that an actor was chosen who could play both the male and female versions of this character in a way that felt natural, and while Hepburn was mainly known for her steadfast femininity, she fit perfectly into dual personas without any difficulty. Joining her on this unconventional journey are Cary Grant, in one of his very first leading roles (and the first of many collaborations with Hepburn and Cukor), and Edmund Gwenn, one of history’s great character actors, playing a sympathetic and earnest paternal role here that gives him the chance to be wildly funny, an increasingly rare opportunity for someone who usually played more patrician characters. The cast is rounded out by the dashing Brian Aherne (who is covetly the second lead, a fact we don’t realize until the end), and the ever-reliable Dennie Moore and Natalie Paley, who may have smaller roles but refuse to be eclipsed by the more bombastic performances. The work being done by these actors may be eccentric and offbeat, but they are certainly an example of their capacity to play more interesting characters, which deserves to be acknowledged, especially when discussing how Sylvia Scarlett was a film undeniably ahead of its times, which extends to the actors and the specific roles they were given to play.

Yet, despite all the conceptual goodwill that drives this film, the aspect that makes Sylvia Scarlett so compelling is the fact that it is simply a well-made, compelling film. It makes its intended genre entirely clear from the outset – there are versions of this story that lean into the melodrama and psychological thriller aspects more prominently, but they lack the elegance of the well-crafted comedy that Cukor is actively seeking when telling this story. One of the factors that strikes us consistently throughout the film is how incredibly modern it feels. Despite the temporal and geographical milieux in which the film takes place, there is something very contemporary about how these characters act and speak, moving through life with a fluidity that makes us wonder how much of Sylvia Scarlett consists of straggling components from the Pre-Code era, since even at its most decidedly tame, there is a controversy that sits right at the heart of the film, a taste for a transgression that Cukor is not quite prepared to discuss just yet, both in terms of his identity and status within the industry, which was not particularly fond of the queer community as dominant artistic voices. which essentially led him to direct several films that had similarly queer undertones, but never made them blatantly obvious. The way the dialogue (which is itself pushing boundaries) is delivered, coupled with the rapid-fire direction and extremely impressive performances are all simple elements that are rendered as absolutely spellbinding while under Cukor’s direction, which aids considerably in elevating Sylvia Scarlett to be one of the more challenging works of queer-toned fiction at a time in which such a description was controversial. To this day, we aren’t entirely sure whether McKenzie wrote the novel to be a statement on identity, but Cukor was certainly not willing to let the opportunity to have this discussion (even indirectly) pass by without at least partially trying to evoke notable points of the broader conversation. All of this compounds to make Sylvia Scarlett one of the more affecting works of romantic comedy from its era, for several challenging and exciting reasons.

Throughout Sylvia Scarlett, we encounter situations that are extremely compelling, but which are also bursting to be explored with a deeper social and cultural perspective – and it may have taken nearly a century, but we seem to finally be in a place where we can appreciate this film as more than just a relic of the past, but a symbol of progress at a time in which such efforts could be perilous, and thus had to be hidden away from the mainstream in creative ways. It is a very simple film with a premise that is effortlessly easy to get right – the only downside of this film was that it was made at a time when audiences could not appreciate the intricate nuances of the story, since gender was still considered a subject that should not be touched, and Cukor certainly was not one to buckle to conventions, with his efforts to skirt around the edges of controversy being quite noticeable. It’s doubtful that this film was made to appeal to future audiences in mind, but it is oddly very prescient, containing elements that would not be seen for several decades, when subversive cinema became much more common, and gender and sexuality were not such controversial subjects. As a whole, Sylvia Scarlett is a very fun film with strong performances and a good sense of humour, and while not every joke lands, and the plot itself can become slightly convoluted in the third act, it is a noble effort that intends to create a very upbeat atmosphere. It is difficult to criticize a film with such strong intentions, and this is certainly a far better film than critics at the time may have been willing to admit, which is all part of the experience that comes with watching a shockingly progressive work, to the point where even modern audiences may be taken by surprise – the only difference being that in the past, it resulted in shock, whereas today, it becomes absolute delight, the perfect result for a film that is truly so endearing and provocative in all the right ways.