Some Like It Hot

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 accidentally 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. 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 to Miami by train. On the train, they 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 Joe 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. Joe and Jerry become close friends with Sugar during a late-night party on the train, while struggling to remember that flirting with her would compromise their cover.

After arriving in Miami, Joe woos Sugar by posing as Junior, heir to the Shell Oil fortune, affecting a Cary Grant-esque accent while feigning indifference to her. Aging, multi-divorced Osgood Fielding III—an actual millionaire—persistently pursues "Daphne" (Jerry), whose refusals only fuel his desire. After Osgood invites Jerry to dinner on his yacht, Joe convinces Jerry to keep Osgood occupied onshore, so Joe can pass the yacht off as his own and entertain Sugar. As Junior, he tells Sugar that psychological trauma from the death of a former lover has left him impotent, but he would immediately marry anyone who could cure him. Sugar tries to arouse him, with considerable success. Meanwhile, Jerry and Osgood tango until dawn. Back at the hotel, Jerry announces that he has accepted Osgood's proposal of marriage, anticipating a divorce and cash settlement when the 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—who already has a grudge against Spats over the murder of Toothpick. Spats and his men arrive, and this time see through Joe and Jerry's disguises. Fearing for their lives, Joe and Jerry realize they must quit the band and leave the hotel. Joe breaks up with Sugar over the telephone, telling her that he must marry a woman of his father's choosing and move to Venezuela, leaving her heartbroken. In male disguises, 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 as they flee through the hotel. They revert to women's clothing to evade capture. On the way out, Joe, dressed as Josephine, sees Sugar onstage singing a lament to lost love, kisses her, then rejoins Jerry in their flight. Realizing that Josephine and Junior are the same person, Sugar follows them.
Still dressed as Daphne, Jerry persuades Osgood to take him and Joe away on his yacht. Sugar unexpectedly joins them on Osgood's launch just as it leaves the dock. Removing his disguise, Joe confesses 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, as Daphne, tries to get out of his engagement, listing reasons why "she" and Osgood cannot marry—she can't wear his mother's wedding gown because she's "not built the same", is not a natural blonde, smokes, cannot have children, has been living with a saxophone player—none of which bother Osgood. Exasperated, Jerry rips off his wig and says, "I'm a man!" in his normal voice. Still unperturbed and smiling, Osgood replies "Well, nobody's perfect!" leaving Jerry speechless.