Charley's Aunt (1956)
Otto Dernburg is forced by circumstances to dress up as a middle-aged woman.
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Very well executed
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Don't Believe the Hype
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It's entirely possible that sending the audience out feeling lousy was intentional
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Watching it is like watching the spectacle of a class clown at their best: you laugh at their jokes, instigate their defiance, and "ooooh" when they get in trouble.
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