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Plot
In Prohibition-era Chicago, Joe is a jazz saxophone player and an irresponsible, impulsive gambler and ladies' man; Jerry, his anxious friend, is a jazz double bass player. They work in a speakeasy owned by local Mafia boss "Spats" Colombo. Tipped off by informant "Toothpick" Charlie, the police raid the joint. Joe and Jerry escape, but later accidentally witness Spats and his henchmen gunning down Toothpick and his gang in revenge (an incident inspired by the Saint Valentine's Day Massacre).[7] Spats and his gang see them as they flee. Broke, terrified, and desperate to leave Chicago, Joe and Jerry disguise themselves as women named Josephine and Daphne so they can join Sweet Sue and her Society Syncopators, an all-female band headed by train to Miami. On the train, Joe and Jerry befriend Sugar Kane, the band's vocalist and ukulele player.
Joe and Jerry become obsessed with Sugar and compete for her affections while maintaining their disguises. Sugar confides to Josephine that she has sworn off male saxophone players, who have taken advantage of her in the past. She hopes to find a gentle, bespectacled millionaire in Florida. Josephine and Daphne become close friends with Sugar during a late-night party on the train and struggle to remember that flirting with her would compromise their cover.
After arriving in Miami, Joe woos Sugar by posing as oil heir Shell Oil Junior and affecting a Cary Grant-esque accent while feigning indifference to her. The aging, multi-divorcee Osgood Fielding III, an actual millionaire, persistently pursues Daphne, whose refusals only fuel his desire. After Osgood invites Daphne to dinner on his yacht, Joe convinces Jerry to keep Osgood occupied onshore so that Junior can be alone with Sugar on Osgood's yacht and pass it off as his own. On the yacht, Junior tells Sugar that psychological trauma from the death of a former lover has left him impotent, but that he would immediately marry anyone who could cure him. Sugar tries to arouse him, with considerable success. Meanwhile, Daphne and Osgood dance the tango (la cumparsita) until dawn. When Joe and Jerry get back to the hotel, Jerry announces that Osgood has proposed marriage to Daphne and that he has accepted, anticipating a divorce and cash settlement when his ruse is revealed. Joe convinces Jerry that he cannot marry Osgood.
The hotel hosts a conference for the Friends of Italian Opera Society, a front for a national Mafia meeting presided over by Little Bonaparte. Spats and his men arrive and soon recognize Joe and Jerry, still in disguise as the witnesses they have been looking for. Fearing for their lives, Joe and Jerry realize they must quit the band and leave the hotel. Joe conceals his deception from Sugar by telling her over the telephone that Junior must marry a woman of his father's choosing and move to Venezuela. Sugar becomes distressed and heartbroken. Joe and Jerry evade Spats' men by hiding under a table at the syndicate banquet, where Little Bonaparte has Spats and his gang gunned down. Joe and Jerry are spotted and they flee through the hotel. Joe, still dressed as Josephine, sees Sugar onstage singing a lament to lost love. After Joe runs onto the stage and kisses her, Sugar realizes that Josephine and Junior are the same person.
Jerry persuades Osgood to take Daphne and Josephine away on his yacht. Sugar runs from the stage at the end of her song and jumps aboard Osgood's launch just as it is leaving the dock. Joe confesses the truth to Sugar and tells her that she deserves better, but Sugar wants him anyway, realizing he is the first man to genuinely care for her. Meanwhile, Jerry tries to get out of his engagement by listing reasons why Daphne and Osgood cannot marry, none of which bother Osgood. Exasperated, Jerry rips off his wig and says "I'm a man!" in his normal voice; still smiling, Osgood replies "Well, nobody's perfect," confounding Jerry and leaving him speechless.
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