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Manhattan (1979)

Synopsis: Director Woody Allen's love letter to New York City stars Allen as frustrated television writer Isaac Davis, a twice-divorced malcontent facing middle age alone after his wife, Jill (Meryl Streep), leaves him for a woman. Isaac is dating fresh-faced Tracy (Mariel Hemingway), a high school girl he knows is wrong for him, and begins to wonder if he and brainy writer Mary (Diane Keaton), the mistress of his best friend, Yale (Michael Murphy), might make a better couple.