2. Some Like It Hot (1959)
In one of the most beloved comedy's of all time, Some Like It Hot follows jazz musicians Joe and Jerry as they escape from mobsters after witnessing the St. Valentine's Day Massacre. In order to hop on the next train out of town, the guys dress up as women and join a traveling band. The band's singer, the Bond-girl-named Sugar Kane, is a blonde bombshell played by Marilyn Monroe. Joe, though in disguise as Josephine, is instantly smitten. Through some ups and downs, Joe manages to win over Sugar's heart and the two end up together. Things don't go as well for Daphne, Jerry's alter ego. Though he's rich enough to own a yacht, Osgood Fielding III just isn't quite as foxy as Marilyn Monroe. Osgood, played by Joe E. Brown, falls hard for Daphne, proposing marriage to her/him to which she/he inexplicably agree. At the end of the film, after Joe has come clean to Sugar with pleasant results, Jerry too comes clean to Osgood. The movie ends with the famous line "nobody's perfect," proof that not only is love blind, but it doesn't mind a 5 o'clock shadow either.