Way back in 1935 Katharine Hepburn and Cary Grant (An Affair to Remember) were to meet for the first time on screen. The results were not what you’d expect given their better remembered history. In fact, there is no romance between the two.

The object of Hepburn’s attention is not Grant but rather Brian Aherne. She and Grant are really more intended as comedy duo along the lines of Abbot and Costello or William Powell and Myrna Loy. But the movie really doesn’t work very well. Even Edmund Gwenn, who plays Hepburn’s father, is wasted in this film as he flails about and attains no sympathy from us, starting with the first scene. 

So, why watch this film at all? Well, it has three interesting aspects to it. Primarily, Hepburn is dressed as a boy for a good part of the film. It is intended to lead to hijinx and hilarity of mistaken intentions and confused sexuality (all with a laugh, of course). It didn’t work then. It works a little better now as gender roles and societal norms have relaxed. A little better. Hepburn is, mostly, a strong character in this story. But there are no guts to the script and barely a good joke, though Hepburn does a game job of jumping back and forth in her makeup and movement. And with Mel Berns make-up, Hepburn almost passes, looking like a young David Bowie in her drag.

The second bit of trivia for this film is Grant. It was, essentially, his breakout. Not with the film itself, but it was the first time his trademark personality on screen was exhibited and noticed. It led to his subsequent stardom.

The final interesting aspect of this film, especially given this summer’s misfires at the box office, was that Sylvia Scarlett was a massive bomb (losing about 350,000 or over 6M in 2017 dollars) when it released. It almost cost Hepburn her career. 3 years later she would return triumphantly, and with Grant again, in Bringing Up Baby (followed in quick succession by Holiday, Philadelphia Story), and then Woman of the Year.

You don’t often get to see what didn’t work from years past. For good reason they tend to fade and be forgotten. In this case, the star power kept it alive until it found an audience, however tenuously. You’d never expect that George Cukor, who would go on to direct My Fair Lady, Philadelphia Story, and Adam’s Rib, just to name a few, was at the helm of this damaged ship. But he did see the spark in the pairing of Grant and Hepburn and got to use it later on.

Sylvia Scarlett is not a great film, even in retrospect. But it is a fascinating piece of film history, with some moments to recommend it. I have to admit, I had to skip a small chunk of the film near the beginning because it was just so uncomfortably bad. But curiosity had me finish it. I also wonder if, in title and nod to theme, they weren’t playing on the previous year’s Marlene Dietrich success: The Scarlet Empress, but I don’t think anyone is left to ask that one anymore.