Some Like It Hot(1959)
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Two musicians witness a mob hit in Chicago and flee the state in an all-female band disguised as women. The mobsters catch up with them in Miami but they are able to ellude them. Joe/Josephine (Tony Curtis) ends up with Sugar (Marilyn Monroe) and the rich yacht guy still wants to marry Jerry/Daphne (Jack Lemmon) even though he’s a guy, and they all sail off together.