Naughty: The Apartment (1960)
Nothing is more awkward than your boss hooking up with your crush. So imagine being Jack Lemmon in Billy Wilder’s The Apartment, whose boss isn’t just sleeping with his crush (Shirley MacLaine) but doing the deed in his own pad! (Even worse: Imagine the cleaning bill on all of his own bedsheets.) Beloved as it may be with its sweet happy ending and the triumph of personal happiness over professional ambition, the central predicament of The Apartment is just about the epitome of the holiday blues. The very kind Elvis sang about.
