The plot: Lonely bachelor C.C. "Bud" Baxter (Jack Lemmon) works long days at a New York insurance company but spends longer nights pacing the streets of Manhattan while his superiors use his apartment for trysts. Baxter quickly rises up the corporate ladder to become assistant to head honcho Jeff Sheldrake (Fred MacMurray). But when Baxter learns Sheldrake has been using his digs to entertain Fran (Shirley MacLaine), the elevator operator with whom Bud is smitten, things get complicated.
Why it's worthy: "'The Apartment' came at a time right before the counterculture when the message was the search for individuality against the establishment, represented by the insurance company," says Pelecanos. "The shots of the offices, the way the desks were aligned, suggest complete conformity." Baxter's moral questioning presaged the youth rebellion and generation gap that soon followed.
Set notes: "The Apartment" won best picture, director and screenplay Oscars for Billy Wilder (see also, "Double Indemnity") and ranks No. 80 on the American Film Institute's 2007 list of the 100 Greatest American Movies of All Time. Lemmon and MacMurray had a knack for insurance films; Lemmon also stars in "Save the Tiger" and MacMurray in "Double Indemnity," which are both on our list.