2. The Apartment (1960)
Billy Wilder again, once more reaffirming his reputation as one of Hollywood’s greatest ever filmmakers by once again upending the conventions of the rom-com in classic fashion.
Jack Lemmon’s insurance worker lends his apartment to his bosses for their extramarital needs, only to find himself disappointed when his boss’ lover turns out to be the woman he’s got the hots for himself.
Forced to choose between the girl he wants and the job he’s been promised, Wilder handles the comedy just as well as the drama with one of the greatest movies ever made in any genre, one that took the box office by storm and won deserved Academy Awards for Best Picture, Director and Screenplay.