Some Like It Hot (1959)

After seeing a Mafia hit, smooth-talking saxophonist Joe (Tony Curtis) and his loyal friend Jerry (Jack Lemmon) quickly come up with a plan to flee Chicago and save their lives. They disguise themselves as women and join an all-female jazz band, catching a train to Florida. While Joe impersonates a wealthy man to charm the band's attractive singer, Sugar (Marilyn Monroe), Jerry becomes the target of a genuine millionaire (Joe E. Brown), all while the mobsters draw closer.