Sylvia Scarlett [1935]

Henry Scarlett (Edmund Gwenn) commits a bit of larceny and is forced to flee France with his daughter Sylvia (Hepburn) masquerading as a boy. Along the way they meet up with Jimmy Monkley (Grant), a cockney ne'er-do-well. In London they start doing some creative swindling, hooking up with a Maudie Tilt (Dennie Moore), a daffy servant girl who becomes Henry's wife. Meanwhile, Slyvia becomes enamored with handsome young artist Michael Fane (Brian Aherne), who, of course, thinks she is a boy. But when Michael starts to fall for Lily (Natalie Paley), Sylvia has to become a woman again to get the man she loves (pretend for the sake of argument that she is going to end up with the guy who gets third billing in the movie).

"Sylvia Scarlett" is based on the 1918 Comptom MacKenzie novel "The Early Life and Adventures of Sylvia Scarlett," but this ends up being Cukor's film and a charming story about vagabond thieves. Hepburn's androgyny does not strike contemporary audiences as being all that odd while Grant is playing the character closest to his own younger days of any in his entire career and stealing all the scenes. Gwenn and Moore are delightful as the less than suitable parental figures for the gang. Certainly compared to other cross-dressing comedies that have been made over the years, "Sylvia Scarlett" actually ends up being relatively realistic. Note: Natalie Paley was actually a Russian princess, the daughter of the Russian Grand Duke Paul, who was an uncle of the late Czar Nicholas, which would make her a cousin of the tragic Anastasia).