Some Like It Hot (1959)

Synopsis
The launching pad for Billy Wilder's comedy classic was a rusty old German farce, Fanfares of Love, whose two main characters were male musicians so desperate to get a job that they disguise themselves as women and play with an all-girl band in gangster-dominated 1929 Chicago. In this version, musicians Joe (Tony Curtis) and Jerry (Jack Lemmon) lose their jobs when a speakeasy owned by mob boss Spats Columbo (George Raft) is raided by prohibition agent Mulligan (Pat O'Brien). Several weeks later, on February 14th, Joe and Jerry get a job perfroming in Urbana and end up witnessing a gangland massacre in a parking garage. Fearing that they will be next on the mobsters' hit lists, Joe devises an ingenious plan for disguising their identities. Soon they are all dolled up and performing as Josephine and Daphne in Sweet Sue's all-girl orchestra. En route to Florida by train with Sweet Sue's band, the boys (girls?) make the acquaintance of Sue's lead singer Sugar Kane (Marilyn Monroe, in what may be her best performance). Joe and Jerry immediately fall in love, though of course their new feminine identities prevent them from acting on their desires. Still, they are determined to woo her, and they enact an elaborate series of gender-bending ruses complicated by the fact that flirtatious millionaire Osgood Fielding (Joe E. Brown) has fallen in love with "Daphne." The plot gets even thicker when Spats Columbo and his boys show up in Florida. Nominated for several Oscars, Some Like It Hot ended up the biggest moneymaking comedy up to 1959. Full of hilarious set pieces and movie in-jokes, it has not tarnished with time and in fact seems to get better with each passing year, as its cross-dressing humor keeps it only more and more up-to-date. ~ Hal Erickson, All Movie Guide