#16: The Apartment (1960)
A romantic dramedy (or dramatic comedy) with a bizarre plotline, Billy Wilder’s The Apartment was more of a hit with fans in 1960 than with critics. Still, that didn’t stop it from becoming an esteemed musical by Burt Bacharach, Hal David, and Neil Simon just a few years later. (Yes, we’re talking about Promises, Promises).
In The Apartment, C.C. Baxter (Jack Lemmon) hopes to win the favor of his boss, Mr. Sheldrake (Fred MacMurray), by lending him his apartment to conduct his extramarital affairs in. It’s only when elevator girl Fran Kubelik (Shirley MacLaine) comes into the picture that the arrangement becomes less than ideal for Baxter.