Crossdressing before 1959? The first title that comes to mind is Sylvia
Scarlett (1935), in which Hepburn dresses as a boy for much of the film.
There were also something like half-a-dozen versions of "Charley's Aunt"
filmed by the 1940s. So there's a start.
JRG
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John R. Groch <[log in to unmask]> | "Work! FINISH! THEN sleep."
English Department/Film Studies Program | -- The Monster,
Univ. of Pittsburgh, Pittsburgh, PA 15260 | "Bride of Frankenstein"
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