Breakfast At Tiffany's (1961)

A young woman (Audrey Hepburn), who lives off men, becomes friends with a struggling writer (George Peppard) who moves into her New York apartment building. As he falls in love with her, she resists his attempts at romance as she has her eye on catching a rich husband. Perhaps Hepburn's most iconic performance, this is an almost irresistible film. Drastically altered from the Truman Capote novella on which it's based (this is one film that really demands a "remake"), the film is elegantly charming and sophisticated that one can excuse the cleaning up of Capote's material: Hepburn's character is essentially a call girl while Peppard's character is gay. The entire film rides on Hepburn's shoulders and she carries it like a champion. The director Blake Edwards (in his breakthrough film) gives us a fantasy New York where everyone is tres chic, the streets are pristine and one can live off $50 tips to the powder room. The gorgeous Oscar winning score is by Henry Mancini and introduced the haunting Moon River. With Patricia Neal, Buddy Ebsen, Martin Balsam, John McGiver, Jose Luis De Vilallonga, Joan Staley and Mickey Rooney as Mr. Yunioshi, whose performance remains controversial.