- After two male musicians witness a mob hit, they flee the state in an all-female band disguised as women, but further complications set in.
- After two Chicago musicians, Joe and Jerry, witness the the St. Valentine's Day massacre, they want to get out of town and get away from the gangster responsible, Spats Colombo. They're desperate to get a gig out of town but the only job they know of is in an all-girl band heading to Florida. They show up at the train station as Josephine and Daphne, the replacement saxophone and bass players. They certainly enjoy being around the girls, especially Sugar Kane Kowalczyk who sings and plays the ukulele. Joe in particular sets out to woo her while Jerry/Daphne is wooed by a millionaire, Osgood Fielding III. Mayhem ensues as the two men try to keep their true identities hidden and Spats Colombo and his crew show up for a meeting with several other crime lords.—garykmcd
- It's the winter of 1929 in Chicago. Friends and roommates Jerry and Joe are band musicians, a string bassist and tenor saxophonist respectively. They are also deep in debt. Womanizing and smooth talking Joe is a glass half full type of guy, who figures they can earn quick money gambling with what little money they earn to pay off their debts, while more conservative Jerry is a half glass empty type of guy. They are in the wrong place at the wrong time when they witness a gangland slaying by bootlegger Spats Colombo and his men, Jerry and Joe managing to make it away from the scene within an inch of their lives. Needing to lay low and get out of town away from Spats, they sense an opportunity when they learn of a local jazz band needing a bassist and a saxophonist for a three week gig at a luxurious tropical seaside resort in Miami, all expenses paid. The problem?: it's an all girl band, but nothing that "Geraldine" and "Josephine" can't overcome, the former who instead chooses Daphne as "her" stage name. Sweet Sue, the band leader, has two basic rules for the band members while on tour: no liquor and no men. Beyond needing to evade Spats and his henchmen, and maintain the front of being women, especially in the most private of situations with the other female band members, Jerry and Joe have two primary problems. First, the more brazen Joe falls for one of the other band members, ukulele player and vocalist Sugar Kane Kowalczyk, although Jerry too is attracted to her. Joe does whatever he can to find time to get out of drag to woo Sugar while in Miami, using all the knowledge Josephine gleans directly from Sugar about what turns her crank in potential husband material. And second, Jerry, as Daphne, catches the eye of wealthy lovestruck Osgood Fielding III, who won't take no for an answer.—Huggo
- After witnessing a Mafia murder, slick saxophone player Joe and his long-suffering buddy, Jerry, improvise a quick plan to escape from Chicago with their lives. Disguising themselves as women, they join an all-female jazz band and hop a train bound for sunny Florida. While Joe pretends to be a millionaire to win the band's sexy singer, Sugar, Jerry finds himself pursued by a real millionaire as things heat up and the mobsters close in.—Jwelch5742
- Two struggling musicians witness the St. Valentine's Day Massacre and try to find a way out of the city before they are found and killed by the mob. The only job that will pay their way is an all girl band so the two dress up as women. In addition to hiding, each has his own problems; One falls for another band member but can't tell her his gender, and the other has a rich suitor who will not take "No," for an answer.—John Vogel <jlvogel@comcast.net>
- It is February 1929 in the city of Chicago. The whole city is under prohibition orders and any sale or purchase of liquor is deemed illegal. The mafia run a booze business by using a funeral parlor as a front and transporting liquor bottles in hearses, hidden inside the coffins. The police are always on the lookout to put the bootleggers out of business.
Joe (Tony Curtis) is a jazz saxophone player, irresponsible gambler and ladies' man; his friend Jerry (Jack Lemmon) is a sensible jazz double-bass player. They work in a speakeasy joint (place where alcoholic beverages are illegally sold, especially such establishments in the United States during Prohibition (1920-33)) owned by local Mafia boss "Spats" Colombo (George Raft).
Tipped off by informant "Toothpick" Charlie (George E. Stone), the police raid the joint. Joe and Jerry escape, but later witness Spats and his henchmen gunning down Toothpick and his gang in revenge (an incident inspired by the Saint Valentine's Day Massacre). Spats and his gang see them as they flee. Joe and Jerry were counting on their paycheck to pay rent and to payoff their creditors.
Joe and Jerry meet their agent Sig Poliakoff (Billy Gray) and his secretary Nellie (Barbara Drew) to get a new gig, but all they have is a 3 week girl band assignment in Florida. Penniless and in a rush to get out of town, the two musicians take a job with Sweet Sue (Joan Shawlee) and her Society Syncopators, an all-female band headed to Miami by train. The band was looking for female bass and saxophone players as their regular girls ran away with their boyfriends just before the band was about to leave.
Disguised as women and calling themselves Josephine and Daphne, they board a train with the band and their male manager, Bienstock (Dave Barry). Before they board the train, Joe and Jerry notice Sugar Kane, the band's vocalist and ukulele player.
Joe and Jerry become enamored of Sugar (Marilyn Monroe) and compete for her affection while maintaining their disguises. Sugar secretly drinks alcohol and is full of life. Sugar's liquor flask is found by Bienstock, and he starts to admonish her as she has been found drunk before. But Daphne steps forward and says that it is her flask, thereby saving Sugar.
Sugar confides that she has sworn off male saxophone players, who have stolen her heart in the past and left her with "the fuzzy end of the lollipop". She has set her sights on finding a sweet, bespectacled millionaire in Florida. During the forbidden drinking and partying on the train, Josephine and Daphne become intimate friends with Sugar and have to struggle to remember that they are girls and cannot make a pass at her.
Once in Miami, Joe woos Sugar by assuming a second disguise as a millionaire named Junior, the heir to Shell Oil, while feigning disinterest in Sugar. An actual millionaire, an aging mama's boy, the much-married Osgood Fielding III (Joe E. Brown), tries repeatedly to pick up Daphne, who rebuffs him. Daphne's refusals only increase his appetite.
Osgood invites Daphne for a champagne supper on his yacht. Joe convinces Daphne to keep Osgood occupied onshore so that Junior can take Sugar to Osgood's yacht, passing it off as his.
Once on the yacht, Junior explains to Sugar that, due to psychological trauma, he is impotent and frigid, but that he would marry anyone who could change that. Sugar tries to arouse some sexual response in Junior and begins to succeed. Meanwhile, Daphne and Osgood dance the tango till dawn.
When Joe and Jerry get back to the hotel, Jerry explains that Osgood has proposed marriage to Daphne and that he, as Daphne, has accepted, anticipating an instant divorce and huge cash settlement when his ruse is revealed. Joe convinces Jerry that he cannot actually 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 gang recognize Joe and Jerry 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 (Nehemiah Persoff) roasts Spats and has him and his men killed.
Joe and Jerry flee through the hotel after being spotted. Joe, dressed as Josephine, sees Sugar onstage singing a lament to lost love. He runs onto the platform and kisses her, causing her to realize that Josephine and Junior were 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 performance 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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