Meg Ryan and Billy Crystal in "When Harry Met Sally." Columbia Pictures Synopsis: Years after a post-college road trip, Harry (Billy Crystal) and Sally (Meg Ryan) reunite in New York City as they ask themselves an age-old question: can a man and a woman be just friends? Why it's so good: From proclamations of love on New Year's Eve to the endlessly quotable diner scene, "When Harry Met Sally" has remained a classic due to Nora Ephron's unparalleled writing. Modern romantic comedies owe a lot to "When Harry Met Sally" (1989). Synopsis: Years after a post-college road trip, Harry (Billy Crystal) and Sally (Meg Ryan) reunite in New York City as they ask themselves an age-old question: can a man and a woman be just friends?