Some Like Hot (1959)

Some Like It Hot (1959) Comedy. Director: Billy Wilder.

Cast: Marilyn Monroe, Tony Curtis and Jack Lemmon.

Federal agent Mulligan, is about to a raid a Chicago speakeasy, run by bootlegger "Spats", based on information he received from "Toothpick". As Mulligan inspects the speakeasy, two members of the band, saxophonist Joe and bass player Jerry, are making plans on how to spend their paycheck. Jerry notices Mulligan's badge and they leave to avoid the police roundup. Looking for work, Joe and Jerry, visit the musician's agency hoping to find another job. The agencies receptionist Nellie, tells them that there is an opening for a bass and sax with a band in an all-expenses paid trip to Florida. Joe and Jerry find out that the positions are in an all-girl band. Later, Joe and Jerry unintentionally witness Spats and his gang shoot Charlie and his gang for ratting out their speakeasy. They are spotted by Spats, but escape in the nick of time. Jerry wants to go to the police, but Joe reminds him they will not be safe from Spats in any part of Chicago. Joe telephones Sid, and using a woman's voice, accepts the job with the all-girl band. Later, that evening at the train station, Joe and Jerry, disguised as Josephine and Daphne, check in with band leader Sue and manager Beinstock, as new members of the Society Syncopators. On board the train, Joe fears that womanizer Jerry will give them away and warns him to act "like a girl".

In the ladies' room, the men/girls met up with singer and ukulele player Sugar, drinking bourbon from a flask. Sugar, begs them not to report her, because she has been warned if she is caught drinking again, she would be fired. During rehearsal, Sugar's flask falls to the floor, Jerry steps forward, and claims the flask is his. That night on the train, (in one of my favorite scenes) Sugar sneaks into Jerry's compartment to thank him for covering for her. Jerry overwhelmed, says that he needs a drink and within minutes a party breaks out. Will these two Drag Queen's be successful in keeping their true identity hidden?

In films like "Tootsie" and "Some Like it Hot" it seems they tone down the fact you have men dressing up in woman's clothing, so you notice the comedy and snappy dialog. The acting of Jack Lemmon, Tony Curtis, and Marilyn Monroe, are wonderful in this film.
FUN FACT:

Director Billy Wilder originally wanted Frank Sinatra as Jerry/Daphne.