1960. dir. Billy Wilder, starring Jack Lemmon, Shirley MacLaine, Fred MacMurray.
Seen it before? No.
It's the pre-Clarence Thomas New York of 1959, at a huge insurance company where all the bosses are nailing their secretaries and assorted other young female employees. And that's where C.C. Baxter (Jack Lemmon) comes in: he allows the higher-ups to use his apartment for their various illicit hook-ups, in exchange for being put on the fast track for promotions. Baxter is a weak-willed pushover, and kind of an annoying dick also. You spent most of the movie wanting to slap him. Anyway, the head of personnel, Mr. Sheldrake (Fred MacMurray), becomes aware of Baxter's operation, and wants in. His mistress is the cute elevator operator, played by Shirley MacLaine, that Baxter had been flirting with. (This is her only movie on the list, and that's good, because she is a pain in the ass.)
Apparently back in the day a comedy could win Best Picture, although this one gets serious in some spots. It's definitely a product of its time. Nowadays the third act would consist of Sheldrake's secretary's slam-dunk sexual harassment lawsuit. I liked the set design here, particularly the insurance office which looks endless. I don't understand why Baxter's apartment is considered such a chick magnet. It looks like a rathole. But anyway, great movie.
Position on the list: 98
Hey! It's that guy!: Ray Walston. Aloha, Mr. Hand!