When Harry Met Sally...is very nearly a perfect film. It stars two performers at their respective peaks: Meg Ryan as adorably neurotic as she'll ever be, and Billy Crystal at his masochistic, hilarious best. Reiner gets the best out of them both with a brisk script that allows both of them room to do their work, and we are rewarded with an improbable chemistry that is still funny and heartwarming decades later.
As much as I enjoyed Meg Ryan at this stage in her career, I am totally in awe of Crystal's talent. He's able to make Harry Burns both appealing and repulsive, sympathetic even as he makes terrible decisions, and amusing throughout, carrying the film's narrative with his constant self-analysis and mild sense of entitlement. He's the poster child of the man-child, a boy who finds himself a man and yet is utterly unprepared for how much work and disappointment maturity entails. That aside, this movie is about the unpaved pathways to love, about how closely related love is to friendship, and how complicated the overlap can be between the two. People like to try to untether the two, to relegate them to distinct boxes, but there's a lot of friendship in love, and a lot of love in friendship.
Harry takes a long time to realize that Sally is the "love of his life" because if nothing else, the film tells us that there's no such thing. Romance and affection and shooting stars are nice, but love is less fairy tale than gritty detective drama, not so much a work of art as a work of work. And when you do find a love worth that labor, you hold on to it as hard as you can. If, in the meantime you can make a woman meow, well...