Once in their room, Jerry, infuriated at being flirted with and pinched by Osgood, demands they give up their disguises and find a male band, but Joe insists they must maintain their masquerade, as Spats will surely investigate male orchestras all over the country.
Upon arriving in Florida at the beachfront Ritz Seminole Hotel, “Daphne” catches the attention of wealthy, oft-married Osgood Fielding III.
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There Sugar confides that she is with the all-girl band in order to escape a series of unhappy love affairs with tenor saxophone players and dreams of finding a sensitive millionaire who wears glasses.
Joe awakens and is horrified, but gets drawn into the festivities when Sugar asks him to help break up an ice block in the ladies’ room. Overwhelmed by Sugar’s proximity, Jerry grows anxious and suggests that he needs a drink and within minutes an impromptu party ensues at Jerry’s berth. That night, Sugar sneaks to Jerry’s berth to thank him for his action, then abruptly jumps into the berth to avoid Sue. A little later during rehearsal, when Sugar’s flask falls to the floor, Sue responds angrily, but Jerry steps forward, and to Sugar’s surprise, claims the flask is his own. Sugar pleads with them not to report her to Sue, who has threatened to fire her if she is caught drinking again. Retreating to the ladies’ room for repairs, the men come upon stunning singer and ukulele player Sugar Kane Kowalczyk drinking bourbon from a flask.
Once on board the train, Joe fears that Jerry’s enthusiasm at finding himself among so many women will expose them and warns his friend to behave “like a girl,” but in the process, musses Jerry’s outfit. That evening at the train station, Joe and Jerry, uncomfortably disguised as women, check in with band leader Sweet Sue and manager Beinstock as the newest members of the Society Syncopators, Joe as Josephine and Jerry as Daphne. Joe then telephones Sid and, using a high falsetto voice, accepts the job with the all-girl band. After they evade the gangsters, Jerry suggests they call the police, but Joe reminds him they will not be safe from Spats in any part of Chicago in spite of the police. Although the musicians are spotted by Spats, he is distracted by Charlie, who revives long enough to allow Joe and Jerry to flee. Retrieving the car at a garage owned by Toothpick Charlie, Joe and Jerry unintentionally witness Spats and his men shoot Charlie and his men to death for informing on the speakeasy. Sid tells them of a job at a college dance in Urbana and Joe accepts, then charms Nellie into loaning them her car for the Urbana gig. Joe and Jerry eagerly question Sid, only to learn that the positions are in an all-girl band. At Sid Poliakoff’s agency, receptionist Nellie Weinmeier, incensed over being stood up by Joe a few nights earlier, reveals there is an opening for a bass and sax with a band in an all-expenses paid trip to Florida. Desperate, Joe and Jerry visit the musicians’ agency building hoping to line up another job. Putting up their coats as collateral, they place a bet with their bookie, and promptly lose both the bet and their coats.
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The longtime friends begin arguing about how to spend their salary until Jerry notices Mulligan’s badge and they make a hasty exit as the raid begins, avoiding the police roundup. As Mulligan inspects the lively speakeasy, two members of the band, saxophonist Joe and bass player Jerry eagerly discuss plans for their salary from their first job in four months. In Chicago, in February, 1929, federal agent Mulligan sets up a raid on a speakeasy run by notorious bootlegger “Spats” Colombo, based on information provided by small-time gangster “Toothpick” Charlie.
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