Meg Ryan, Billy Crystal, ...
Credit: Everett Collection

Upon its release, When Harry Met Sally… seemed like a shameless Hollywood rip-off of Woody Allen’s masterpieces Annie Hall and Manhattan. There were so many similarities — the Jew-shiksa romance, the lush autumn New York City foliage, the ivory-tinkling Gershwin standards, even the white credits set on a black background. But two decades later, the movie — now in a new collector’s edition — plays as a loving homage to a director who had already lost his romantic-comedy way. And as it turns out, Rob Reiner’s film about two friends (Crystal and Ryan) trying to have a platonic relationship was ahead of its time.

In 1989, we were oblivious to the fact that men are from Mars and women are from Venus. Sex and the City‘s knack for labeling guys from the Manhattan singleton’s perspective wouldn’t permeate the culture for nine more years. Writer Nora Ephron’s catchphrases — ”transitional person,” ”high maintenance” — were fresh, and the movie’s central question — ”Can men and women be friends?” — was still titillating. But truth be told, Harry isn’t so much about that query as ”When will Harry sleep with Sally?” and ”When will Harry realize he loves Sally?” Getting to those inevitabilities is sweetly satisfying thanks to the chemistry between Crystal and Ryan. Of course, there are hilariously quotable performances by Carrie Fisher (”Thin. Pretty. Big tits. Your basic nightmare”) and the late Bruno Kirby (”You made a woman meow?”). And today those now-clichéd revelations (women fake orgasms!) seem downright charming.

A rare synchronicity brought it all together: Reiner, Ephron, and Crystal collaborated seamlessly, as we hear on the trio’s juicy new commentary, which feels like a brunch with old friends. Many of their tales are also retold in the collector’s edition’s seven rather run-of-the-mill featurettes. Reiner, divorced from Penny Marshall and feeling ”hopeless,” had come up with the idea. Ephron wrote draft after draft (in the first, Harry and Sally didn’t get together, but Reiner put the kibosh on that because, really, what a bummer). Crystal improvised a lot; he even came up with the classic line uttered by Reiner’s mother (”I’ll have what she’s having”). The elegant coincidence of Reiner meeting his second wife, Michele Singer, while filming the movie — because of filming the movie (cinematographer Barry Sonnenfeld fixed them up on set) — gives it a double happy ending.

Harry takes us back to a simpler time. When Meg Ryan’s lips didn’t overshadow her performances. When answering machines were our most sophisticated telecommunication tool. And when being single in Manhattan was a novelty rather than an obsessively chronicled aspirational industry. A-