Two struggling musicians, Joe and Jerry (Curtis and Lemmon), witness what looks like the Saint Valentine's Day massacre of 1929. When the Chicago gangsters, led by 'Spats' Columbo (Raft) spot them, the duo flee for their lives. They escape and decide to leave town, only to find the sole out-of-town jobs available are in an all-girl band headed to Florida. The two disguise themselves as women, calling themselves Josephine and Geraldine (later Jerry changes his pseudonym to Daphne), join the band and board a train. Joe and Jerry both fall for "Sugar Kane" (Monroe), the band's sexy Polish-American vocalist and ukulele player, and fight for her affection while maintaining their disguises. In Florida, Joe woos Sugar by assuming a second disguise as a millionaire named "Junior", the heir to Shell Oil, while mimicking Cary Grant's voice. An actual millionaire, Osgood Fielding III (Brown), falls for Jerry in his Daphne guise. One night Osgood asks Daphne out to his yacht. Joe convinces Daphne to keep Osgood ashore while he goes on the yacht with Sugar. That night Osgood proposes to Daphne who, in a state of excitement, accepts, believing he can finagle a large settlement from Osgood immediately following their wedding ceremony. When the mobsters arrive at the same hotel for a conference honoring "Friends of Italian Opera", Spats and his gang spot Joe and Jerry. After several humorous chases (and witnessing yet another mob murder), Jerry, Joe, Sugar, and Osgood escape to the millionaire's yacht. Enroute, Sugar tells Joe that she's in love with him and not with "Junior". Jerry, for his part, tries to explain to Osgood that he can't marry him, but Osgood is oblivious to all of Jerry's objections and remains determined -- to the very end—to go through with the marriage; finally, Jerry removes the wig and yells, "I'm a man!", prompting Osgood to utter the movie's memorable last line: "Well, nobody's perfect."

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