In terms of cross-dressing playing a major role in a movie prior
to "Some Like It Hot".  One that comes to mind is "Sylvia Scarlett"
in which Katherine Hepburn dresses as a boy in order to track down
her father (co-starring Cary Grant--their first movie together--
1935).  Cary Grant himself spends some time in drag in 1949's
"I Was a Male War Bride
in which he a British Officer marries American officer Irene
Dunne and in order for him to be able to come to the states after
they marry he has to be classified as a war bride, given that
that this was a unique situation back in the forties (a woman
officer whose husband is moving back with her to her country of
origin). He is dressed as a man during most of the movie, but
the movie touches on some interesting gender issues.   There's
also Greta Garbo, I believe, in "Queen Cristina" who does a
brief stint as a male in the movie.  Also I was mistaken earlier
Grant was with Ann Sheridan in "...Male War Bride" . "Queen
Cristina" was 1933 (as I implied earlier, Garbo does a male sting
(that's stint, not sting) in at least one of her movies, and
I believe this one's it).
 
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