Sylvia Scarlett (1935)

Synopsis
This big-budget 1936 RKO Studios picture lost money, perhaps due to a cool box-office reception to the idea of leading lady Katharine Hepburn in drag, and a rare-for-its-day screen kiss between two women. Edmund Gwenn plays the title character's father Henry, who is obsessed with gambling. His daughter Sylvia (Hepburn) has stolen some expensive lace which they hope to smuggle from France to England. To elude police, she cuts her hair short and disguises herself as a man. She and her father board a ship, and a drunken Henry confesses their scheme to Jimmy Monkley (Cary Grant), a jewel smuggler. To divert attention away from him, Jimmy snitches on Henry to the customs officials, and Henry has to pay up or be arrested. Later, Sylvia confronts Jimmy on a train and punches him. Jimmy apologizes and cuts them in on a scheme to steal jewels from a wealthy family, using his friend Maudie (Dennie Moore), a maid in the house. But Sylvia, still disguised as a man, talks Maudie out of it, and she responds with a kiss. Maudie and Sylvia's father fall in love and Maudie, an aspiring actress, invests money in a show to open in a seaside resort. There they are invited to the mansion of a wealthy artist, Michael Fane (Brian Aherne), who is unsettled by Sylvia's obvious affections before finally discovering that she's a woman. Jimmy is attracted to Michael's roommate, the Russian-born Lily (Natalie Paley) -- and from there, the romantic entaglements between the aformentioned parties proceed like a Shakespearean comedy. ~ Michael Betzold, All Movie Guide