‘When Harry Met Sally’ Turns 30: A Rom-Com That Defined the Genre By Breaking the Rules

Here’s an experiment you can try at home: Ask the person nearest to you to name a romantic comedy, and if they don’t say When Harry Met Sally, I will personally Venmo you $20. (I will not actually do this.) Though it’s been 30 years since its release, When Harry Met Sally is still the quintessential romantic comedy. It’s on the top of every best rom-com list, and it’s the go-to comparison for any new film in the genre. I’ve lost count of the number of films that have been called, by critics and creators alike, “the [insert descriptor here] version of When Harry Met Sally.” (See: Always Be My Maybe; The Big Sick; Definitely, Maybe; Love & Basketball; etc).

Both a box office and a critical success when it came out in 1989, When Harry Met Sally was the third feature from writer Nora Ephron, who loosely based her lead characters on herself and director Rob Reiner. Billy Crystal starred as Harry, an arrogant, sarcastic, and lonely man who would be insufferable had anyone other than the inherently-likable Crystal played him. Meg Ryan was the perfect Sally, always ready to call Harry out on whatever misogynistic bullshit he was spewing. (My favorite: “I just didn’t want to sleep with you, and you had to write it off as a character flaw.”) It was, and is, undeniably, a great movie. But what exactly was it about this film that powered it’s now 30-year status as the reigning romantic comedy queen?

Despite its reputation as a traditional classic, When Harry Met Sally is not really a traditional movie script. A re-watch of the film will, in addition to bringing you joy, remind you that not a whole lot actually happens in this movie. The characters wander around New York City, grab meals at various restaurants, and of course, exchange much witty banter, but Ephron flagrantly disregards the “show don’t tell” rule of screenwriting. We don’t see Harry’s breakup with his wife, but we hear about it in detail when he relays it to his best friend, Jess (Bruno Kirby), at a football game, pausing periodically to dutifully stand up for the wave—which, by the way, is one of the greatest visual gags in cinematic history. We don’t witness Sally burst into tears when her friend’s daughter “spies” a family in a game of “I, Spy,” but we feel like we did, because a Meg Ryan monologue is worth a thousand flashbacks.

Ephron’s dialogue is “on-the-nose,” but what is usually considered a cardinal sin of too-obvious screenwriting, works. That’s in part because it’s just so funny, in part because the actors are just that good, and in part because Ephron stripped away all the non-essential scenes of the genre. Some romantic comedies (including some of Ephron’s later films) feature a contrived situation that gets two people together: A woman gets sent back to high school (Never Been Kissed), two people must pretend to be engaged (The Proposal), or, more recently, a man discovers he’s the only person in the world who remembers the discography of the Beatles (Yesterday). Those concepts are fun and can work, but they can also overshadow what actually makes a romantic comedy good: the relationship between the characters.

It’s true that When Harry Met Sally attempts a half-hearted concept, one which was played up considerably in the marketing campaign: Can men and women be friends? But the truth is, that question is answered within in the first 30 minutes—Harry and Sally do become friends. Even then, the “gimmick” revolves around the relationship: their friendship. There is no character vs. plot; the characters are the plot. There is no waiting for the movie to get to the good stuff, because it’s all the good stuff. That first banter over an 18-hour car ride, that late-night phone call to watch Casablanca together, the fake orgasm in Katz’s Delicatessen, the failed double-date, Sally comforting Harry after he sees his ex-wife, Harry comforting Sally after her ex gets engaged, that first night together, Harry’s speech on New Year’s Eve—all of it. How could you forget a single shot of this film, when every scene is so deliciously romantic and so refreshingly fun?

Of course, the film couldn’t have pulled off its low stakes and lack of action without the perfect team of actors. And it’s not just the chemistry between Ryan and Crystal that’s electric—it’s also the chemistry between Ryan and Fisher, Crystal and Kirby, and Fisher and Kirby (the last pair, sadly, both gone far too soon). They are an irresistible foursome, the kind with whom you long to be best friends. Don’t even get me started on that beautiful four-way phone call scene.

So why is When Harry Met Sally rooted so deep in our culture? Because it was all the best parts of a romantic comedy, none of the worst, with just the right cast. Other films have done that since, of course—The Big Sick comes to my mind as a very strong contender for the throne—but none have done it in a way that’s resonated in quite the same way. Happy 30th to a great film, and may it reign for many years to come.

Where to stream When Harry Met Sally...