Dir: George Cukor
There were certain parts of this that sort of reminded me of Only Angels Have Wings (1939), and it's mostly where the cast works great as an ensemble. Cary Grant being awesome here again probably had something to do with it too. But at the end of the day, this is a Katherine Hepburn vehicle, and you kind of have to like the way she drives it. As for me, it definitely has great moments, but at the end it can't really be called a great film.
Playing up Hepburn's latent androgyny and her inclination to wear men's clothing in public, Sylvia Scarlett is about a father (Edmund Gwenn) and his daughter (Hepburn) who have to leave France for England after he is caught embezzling. So right away there are some character issues with the supporting cast, which continues with slick "gentleman adventurer", aka con-man, Jimmy Monkley (Grant) and a lusty, simple housemaid (Dennie Moore). The cops are looking for man and a girl so Sylvia cuts her hair and becomes Sylvester. Once in England they play some con games but have no luck (in part because Hepburn is so righteous) so they decide to start a traveling performance act and put on pantomime shows. The caravan shots are sort of like The Seventh Seal (1957), but not really. I was reaching for some connection, and this hit the target if only marginally. Sylvia falls for a tall painter (Brian Aherne) but he already has a "lady friend" which causes a lot of hormonal confusion and changes in clothing for young Sylvia.
Hepburn acts her face off in this, but I'm not so sure if that helps a whole. Especially when she's trying to be feminine. She's much more at ease in scenes where there's just "guy" talk going on and she and Grant are bickering. Grant is just a sleazeball here, and at the end, though there's a sort of a wry smile about it, his decision, while not out of character, threw me for a loop. I'd say he gets pretty close to being as great as Geoff Carter in Wings as a role you just don't expect him to have (morally conflicted/ambiguous). The best parts are sort of strange Hawks-esque controlled chaos, like at the mansion where Sylvia gets drunk and Jimmy tries to filch the jewelry, and then the party at the painter's house where everyone is pretty much wasted again and dancing around.
There's just too much Hepburn time though, annoying monologues, crying close-ups and such. I think that stuff was thrown in there as a draw, because all the cross-dressing (and not to mention that scandalous "girl-on-girl" kiss -- wowza!) did not make this a popular film in the 30s and it was a bomb. I think that is why this is on a few cinephile lists; the belief that they found this film that was trashed and now, in retrospect, they can point at how ballsy this was and say, "A half century before Hilary Swank was the obvious choice for boot-cut denims, Hepburn was gallivanting around in suits." Sorry, don't really care. For a romantic comedy, the romance or comedy was not very interesting.
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