Some Like It Hot (1959) on Netflix

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.