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Here's a list of award-winning comedic films where a character's scheme includes pretending to be a member of the opposite sex.1. A Funny Thing Happened on the Way to the Forum (1967) -- Too many plot complications and schemers to mention as Roman slave Zero Mostel plots to unite would-be lovers, securing his freedom. He convinces fellow slave (and fellow real-life McCarthy era blacklisted actor) Jack Gilford to impersonate the girl during a frantic chase scene. Best Music Oscar.

2. Tootsie (1982) -- Actor can't get job as himself because he's so annoying. (Naturally played by Dustin Hoffman.) Best Supporting Actress Jessica Lange and dressing like a matron teach him about his softer side.
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3. Some Like It Hot (1959) -- Classic film where musicians disguised as girl band members escape gangsters. Lots of Oscar nominations, snagging Best Costume Design, but Jack Lemmon and Tony Curtis made the flapper costumes work.

4. Victor/Victoria (1982) -- Despite numerous acting nominations, the music brought the Academy Award home. Julie Andrew's female character pretends she's a female impersonator, gaining nightclub fame. Hmm, cross-dressing-for-jobs themes in 1982. (See No. 2.) Post-feminist response, perhaps?

5. Mrs. Doubtfire (1993) -- Irresponsible Robin Williams disguised as older woman nanny, scamming his family to remain in their lives; possibly unique to the '90s as representing family values. Surprisingly not a Best Costume win for flammable breast prothesis, but a Best Makeup Oscar.
5.5. To Be or Not To Be (1942) -- This is a cheat entry. Skip the acceptable Mel Brooks 1983 remake with an added gay character escaping Nazi roundup by donning a dress. Instead, locate the superior original, where Jack Benny, playing a Polish actor ham trying to both foil the Third Reich and feed his inflated ego, impersonates a German officer. Although critics panned the too-timely satire, it still garnered a music score Oscar nomination.


