If you were trying to find a consensus pick for the best romantic comedy of all time, 1989’s When Harry Met Sally would definitely be a huge part of the conversation, if not just the clear-cut winner. It’s the rom-com that forever changed the nature of rom-coms, and you can find traces of When Harry Met Sally’s DNA in virtually every romantic comedy that’s been made since. A funny but pessimistic male lead paired with a neurotic but optimistic female one? Check. Quirky supporting characters who have a subplot about falling in love with each other? Check. A climax that ends with someone running through the streets in order to confess their love? Check. Along with the commercial success of 1990’s Pretty Woman, When Harry Met Sally helped kick off the romantic comedy renaissance of the 1990s. And it launched the rom-com career of one of the genre’s most important contributors, Nora Ephron.

With When Romance Met Comedy, Caroline Siede examines the history of the rom-com through the years, one happily ever after (or not) at a time.

Although Ephron has sole writing credit, When Harry Met Sally is a triumph of collaboration. (The famous “I’ll have what she’s having” line was suggested by Billy Crystal, and Meg Ryan helped come up with the fake-orgasm-in-a-diner scene in the first place.) The idea for the film grew out of lengthy discussions between Ephron and director Rob Reiner, who began meeting in 1984 to brainstorm a project they could collaborate on. Reiner was still figuring out life as a single man following his divorce from Penny Marshall, and he brought up the idea of a film about two people navigating the way sex impacts their friendship. Ephron liked the concept and set about writing the screenplay.

When Harry Met Sally opens in 1977, with the acrimonious first meeting of Crystal’s Harry and Ryan’s Sally during an 18-hour road trip from Chicago to New York City. Both at the height of post-collegiate pretentiousness, they butt heads over Harry’s theory that men and women can’t be friends without sex getting in the way; once they arrive in New York, they part ways for what they assume will be forever. Five years later, the pair briefly reconnect as 26-year-olds on their way up in the world. Five years after that, they meet again as world-weary people coming out of long-term relationships and disinterested in dating. The bulk of the film centers on the next two years, which Harry and Sally spend building a friendship that eventually blossoms into something more.

As video essayist Michael Tucker of Lessons From The Screenplay points out, that lengthy timeline gives When Harry Met Sally a distinct structure. The film stretches the familiar “enemies into lovers” tropes across more than a decade, allowing its character to believably mature in the intervening years. In my column on Bridget Jones, I argued that the best rom-coms center first and foremost on character growth, not romance. And that’s true of When Harry Met Sally. Harry and Sally are very different people at 31 than they were at 21; where they once brought out the worst in each other, they later bring out the best.

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Like Harry and Sally, Nora Ephron took an unconventional path to her happy ending in the rom-com genre. Her first love was journalism and after graduating from Wellesley College in 1962, she fought tooth and nail to find her place in a still very male-dominated field. (The canceled-too-soon Amazon series Good Girls Revolt dramatized some of that history with Grace Gummer as Nora.) Ephron eventually found success as a reporter and columnist whose wit and humor drew her comparisons to Dorothy Parker. She got a taste for screenwriting and a notable calling card while collaborating with her then-husband Carl Bernstein on an adaptation of his book All The President’s Men. Their script was eventually dropped in favor of one by William Goldman, but a few years later Ephron teamed up with director Mike Nichols on the 1983 Meryl Streep whistle-blowing drama Silkwood. She and co-writer Alice Arlen earned Academy Award nominations for Best Original Screenplay.

But while her path to Hollywood success was in some ways a circuitous one, in other ways screenwriting was in Nora Ephron’s blood. Her parents were a screenwriting duo who had written films like the Fred Astaire musical Daddy Long Legs and the 1957 Spencer Tracy/Katharine Hepburn rom com Desk Set. Phoebe and Henry Ephron raised their four daughters with the expectation that they too would be writers, which is exactly what happened. “Everything is copy,” was Phoebe’s life philosophy and on her own deathbed she told Nora, “Take notes.” Perhaps because of the way she was raised, Nora Ephron was never shy about using her own life in her writing. When she found out Bernstein was cheating on her while she was raising their toddler son and pregnant with their second child, Ephron turned that into the basis for her debut novel, Heartburn.

Ephron applied her “write what you know” philosophy to When Harry Met Sally too. According to Reiner, she based Harry on him and Sally on herself. Like Reiner, Harry is a cynical but funny divorcé. And like Ephron, Sally is a woman with unabashedly specific taste in just about everything. Ariel Levy’s delightful 2009 New Yorker profile on Ephron reveals that she preferred not to style her own hair and instead went to a beauty parlor twice a week to have it washed and blow-dried. A famed foodie who would go on to write and direct Julie & Julia, Ephron was as picky about her food orders as Sally. Of course, it’s also worth remembering that Ephron had already been divorced twice by the time she started work on When Harry Met Sally, which probably helped inform the character of Harry as much as Reiner’s experiences did.

But even more so than personal quirks, what Ephron brought to the table as a writer was the ability to ask questions and to listen—skills she’d honed as a journalist. Ephron began her writing process by interviewing both Reiner and producer Andy Scheinman about their lives as single men. She also interviewed people at the film’s production company about their own love lives, which became the basis for the faux documentary footage of couples scattered throughout the film. She even took inspiration from the real-life friendship of Reiner and Crystal, who used to lie in their beds and watch TV “together” over the phone. Ephron turned that into a ritual that establishes the intimacy between Harry and Sally.

Perhaps because Ephron took so much from real life, When Harry Met Sally is a surprisingly grounded romantic comedy. It’s made up largely of low-stakes hangout scenes that have more in common with today’s more realistic rom-coms than they do the glossy rom-coms of the 2000s. For instance, the film contains perhaps the most hilariously accurate depiction of a game of Pictionary
ever captured on screen. Although the dialogue often has the patter of a play, Reiner and Ephron anchor those well-written conversations in the natural milieu of New York City life. Harry and Sally discuss their dating lives while unrolling a rug or wandering through Central Park or spending a day at The Met, delivering silly banter in goofy voices.

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In his 2014 retrospective for Grantland, Mark Harris positions When Harry Met Sally as the film that bridged the gap between Woody Allen’s more niche rom-coms of the 1970s (particularly Annie Hall) and the mainstream rom-coms Ephron’s film would go on influence. When Harry Met Sally keeps Allen’s neurotic male lead, love of New York City, and probing questions about the nature of relationships. But it also softens the Allen formula and roots it in the earnestness that defined so much of Ephron’s and Reiner’s work. Plus, thanks to Ephron, it gives its female lead a neurotic depth of her own. As Harris puts it, that tweaked formula led to “a tectonic realignment” in the romantic comedy sphere, and not just on film. Both Seinfeld and Friends are New York-set shows partially anchored around the question of whether men and women can just be friends.

In terms of realism, it helps that Billy Crystal isn’t an impossibly dashing romantic lead, but a guy who seems like he could actually exist in the real world. In the wrong hands, Harry could be a hugely unlikable character, but Crystal is careful to layer Harry’s cynicism with charm rather than harshness. Similarly, Meg Ryan keeps Sally’s “high maintenance” behavior from feeling either too twee or too irritating. Her specialized way of ordering food doesn’t feel like a quirk she’s putting on to get a rise out of others, but a natural part of who Sally is. That’s because Ryan always grounds Sally’s behavior in logic—even when it’s a logic only Sally can follow. Plus it helps that Bruno Kirby and Carrie Fisher are on hand as the best friend characters who bring a slightly more earthy presence to the material (and get their own sweet love story in the process).

When Harry Met Sally turned Crystal, already a prominent comedic voice on TV, into a bonafide movie star, and it was even more of a breakout role for the lesser-known Ryan. In retrospect—and because of how strongly we still associate them with these roles—it’s easy to think that both performers are simply being themselves on screen. But that does a disservice to the thoughtful work they do in bringing these characters to life. Particularly in that 1977 opening sequence, Crystal and Ryan excel at creating youthful characters who feel different from but still of a piece with the people Harry and Sally go on to become later in the film.

One of the most remarkable things about rewatching When Harry Met Sally is just how timeless it feels, 29 years after it was released. While the landline phones and shoulder pads now look hopelessly dated, the film doesn’t. A lot of that has to do with the soundtrack, which made the smart choice to eschew late ’80s hits for a classic big band sound arranged by Marc Shaiman and performed by then relative newcomer Harry Connick Jr. So while When Harry Met Sally takes place over the course of a very specific 12-year period, it also feels like a movie removed from time, something the talking head interviews help drive home. This is the story of one particular couple, but it’s also a story about love in general.

The most dated, and I’d argue least interesting, aspect of When Harry Met Sally is actually its famed central question: “Can men and women just be friends without sex getting in the way?” It’s a pretty limiting—not to mention heteronormative—way to look at the world. But, thankfully, investing in that question isn’t particularly necessary to enjoy When Harry Met Sally, which works better as an examination of a certain type of friendship a lot of people find themselves in, particularly in their 20s and 30s. After bad breakups, Harry and Sally use their friendship as a stand-in for the emotional intimacy they actually want from a romantic relationship. They become platonic life partners in a way that starts out as a healthy friendship but ultimately becomes unhealthy because it’s preventing them from growing. “Someone to dance with on New Year’s Eve” becomes “the person who stops you from wanting to dance with anyone else on New Year’s Eve.” In other words, it’s a film less about sex and more about emotional intimacy.

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That’s why the film’s pitch-perfect climax isn’t about Harry and Sally falling into bed together (that happens earlier and is played largely for laughs) and their final kiss is more of a denouement than an exclamation point. Instead the real emotional climax comes when Harry pushes back against Sally’s idea that he’s just saying he loves her because he’s sad that he’s alone. “It’s not because I’m lonely,” Harry explains, “and it’s not because it’s New Year’s Eve. I came here tonight because when you realize you want to spend the rest of your life with somebody, you want the rest of your life to start as soon as possible.”

As Mark Harris put it, “The sad/scary undertow of every romantic comedy is ‘What if I’m not in a romantic comedy but a melodrama? What if it never works out for me?’ By letting them—and all of us—feel that tug, the movie finds its stakes.” Originally, Ephron and Reiner wanted to give the film a more bittersweet ending in which Harry and Sally didn’t end up together. But like so many of the best rom-coms, this one takes a relatable core idea—in this case the messy line between friendship and romance—and gives it the sweeping happy ending plenty of real-life relationships don’t get.

It’s that ability to blend fantasy with reality that made Ephron such a perfect rom-com creator. She earned her second Oscar nod for When Harry Met Sally and her third for her next Meg Ryan-led rom-com, 1993’s Sleepless In Seattle. Ephron rounded out her Meg Ryan trilogy by re-pairing Ryan with her Sleepless In Seattle (and Joe Versus The Volcano) co-star Tom Hanks in 1998’s You’ve Got Mail. Ephron also directed those latter two films, something she did with almost all her scripts in the second half of her career. As Ephron explained:

Most directors, I discovered, need to be convinced that the screenplay they’re going to direct has something to do with them, and this is a tricky thing if you write screenplays where women have parts that are equal to or greater than the male part. ... You look at a list of directors and it’s all boys; it certainly was when I started as a screenwriter. So I thought, I’m just going to become a director and that’ll make it easier.

Those three films—When Harry Met Sally, Sleepless In Seattle, and You’ve Got Mail— are all icons in the romantic comedy genre, and it’s truly remarkable that they all came from the heart and soul of one creative force. Ephron deserves to be celebrated as a major player within the rom-com genre (and elsewhere), and as a trailblazing female filmmaker who told unapologetically female stories along the way. Though all three of Ephron’s Meg Ryan-led films would have staunch defenders in a debate to determine the best rom-com of all time, for my money When Harry Met Sally is a snapshot of Ephron—and just about all of its major players—at their very best. It’s no wonder that romantic comedies have been trying to recapture the movie’s ephemeral magic ever since.

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Next time: The Big Sick lovingly updates the rom-com formula.