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The Apartment (1960)
Plot: A Manhattan insurance clerk lends out his apartment for executives to use for their illicit affairs. Along the way, he falls in love with the feisty elevator operator in his building, but nothing goes as planned.
What's in it for guys and girls alike: "The Apartment" has a romantic soul, buried in a masterfully cynical shell. Or maybe it has a cynical soul buried in a masterfully romantic shell. Either way, Billy Wilder's writing (with I.A.L. Diamond) has never been sharper, nor his satirical eye more probing. It's a movie that can veer from broad slapstick to well-earned pathos in seconds, an obvious tribute to Wilder and the performances by Jack Lemmon, Shirley MacLaine and Fred MacMurray. This goes for guys or gals: Watch "The Apartment" with your Valentine. If they don't love it, it's time to lease that apartment in your heart to somebody else.
- Daniel Fienberg