When Harry Met Sally… (1989) (SPOILERS) When Harry Met Sally… is undoubtedly indebted to the oeuvre of Woody Allen, but I disagree with those who dismissed it as a shallow steal of his best moments. It lands somewhere between the Allen of Annie Hall and the knowing New York-ness of Seinfeld (and like the latter, it is remarkably honed; there isn’t an ounce of fat on it). But what mostly distinguishes the picture is that it allows itself warmth and optimism in a manner Allen would surely have scorned. Woody’s “romcoms” were all about the bittersweet, about reflecting on the loss of love in a melancholic manner. So while I’d never suggest When Harry Met Sally… is a better movie, or a better comedy, than Annie Hall , it is a more satisfying romantic comedy.