It is February 1929 in the city of Chicago , during the era of Prohibition . Joe ( Tony Curtis ) is a jazz saxophone player , and an irresponsible gambler and ladies ' man ; his sensible friend Jerry ( Jack Lemmon ) is a jazz double bass player . They work in a speakeasy ( disguised as a funeral home ) owned by gangster " Spats " Colombo ( George Raft ) . Tipped off by informant " Toothpick " Charlie ( George E. Stone ) , the police , led by treasury agent Mulligan ( Pat O'Brien ) , raid the joint . Joe and Jerry flee — only to accidentally witness Spats and his henchmen exacting revenge on " Toothpick " and his own gang ( inspired by the real-life Saint Valentine 's Day Massacre ) . Broke , and desperate to get out of town , Joe and Jerry disguise themselves as women named Josephine and Daphne , so they can join Sweet Sue ( Joan Shawlee ) and her Society Syncopators , an all-female band headed to Miami . They board a train with the band and its male manager , Bienstock ( Dave Barry ) . Joe and Jerry notice Sugar Kane ( Marilyn Monroe ) , the band 's vocalist and ukulele player
Saint Valentine 's Day Massacre
Saint Valentine's Day Massacre
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