The Apartment (1960)

You’ll find yourself saying again and again through this wise, eyes-wide-open comedy: They made this in 1960? Its setup — a young clerk has to loan out his apartment to executives who use it for secret trysts with vulnerable women — is grim even by modern standards.

But you find yourself quickly rooting hard for the irresistible Shirley MacLaine and begrudgingly heroic Jack Lemmon. You don’t have to look hard to find a very modern metaphor here about refusing to take it from the man.

MacLaine, Lemmon, director Billy Wilder and screenwriter IAL Diamond reunited three years later for Irma la Douce, which revisited some of the themes of The Apartment.