Set in 1929 Chicago, Some Like It Hot follows two musicians, Joe (Tony Curtis) and Jerry (Jack Lemmon), who witness the St. Valentine's Day Massacre. To escape the mobsters led by "Spats" Colombo (George Raft), they disguise themselves as women, taking on the names Josephine and Daphne, and join an all-female band heading to Florida. Their plan gets complicated when they both fall for the band's beautiful and vulnerable singer, Sugar Kane (Marilyn Monroe).
Once in Miami, the deception deepens. Joe, as Josephine, befriends Sugar to learn what she desires in a man. He then adopts a second disguise as a Cary Grant-esque millionaire named "Junior," the heir to the Shell Oil fortune, to woo her. Meanwhile, Jerry, as the vivacious Daphne, finds himself relentlessly pursued by a genuine, and very persistent, millionaire, Osgood Fielding III (Joe E. Brown). The situation becomes a frantic juggling act of maintaining their disguises, dealing with their romantic entanglements, and avoiding the gangsters who have also arrived in Florida for a convention.
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