Billy Wilder‘s acerbic look at corporate life, The Apartment, stars Jack Lemmon as an ambitious insurance clerk desperate to get ahead at work. While trying to romance beautiful elevator operator Shirley MacLaine, he starts letting his married managers use his bachelor pad for their trysts in order to advance his career. But his plan backfires when he discovers that boss Fred MacMurray is romancing MacLaine. Winner of five Oscar, including Best Picture, Director, and Screenplay. Obviously, this movie is about as classic as classics get…which makes it ripe for a Create-A-Caption skewering. We’ve taken a still from the film and given it a comedic spin below, and you can join in the fun by leaving your own in the comments below!