‘When Harry Met Sally’: How Nora Ephron Sold Woody Allen to the Masses

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The film opens with simple, white-on-black titles, backed by an elegant, evocative jazz standard. The story that follows, framed by documentary-style straight-to-camera interviews, concerns a witty, urbane Jewish neurotic and his relationship with a sunny, fashionable shiksa. They stroll in through an autumnal Central Park and discuss death, sexual hang-ups, and New York real estate; the borough of Manhattan is captured in loving beauty shots, often backed by the music of Louie Armstrong. From that description, it would be easy to assume I was describing any number of Woody Allen films (Annie Hall in particular). But no, I’m talking about director Rob Reiner and screenwriter Nora Ephron’s When Harry Met Sally… which hit theaters 25 years ago today and made a mint — its $92 million gross easily besting any Allen film to this day. So how did Harry do so well (big money, cultural capital, ongoing influence over the romantic comedy genre) when its clear inspiration remains such an acquired taste?

Before we begin, there are two things worth clarifying: first, remember that Harry hit theaters three years before the Allen/Farrow breakup (and its many troublesome revelations), so while that scandal may have affected the comparative legacies of the works, it doesn’t explain that initial financial windfall. And second, I feel it’s important to make this clear: I like When Harry Met Sally. I saw it on its initial theatrical release, laughed heartily, quoted its best lines, and revisited it frequently. But in the subsequent years, as I spent more time with the filmography of Mr. Allen, I noticed how much of Harry seemed… familiar.

First of all, there are those faux-documentary interviews, which immediately recall Allen’s Zelig from a few years earlier (to say nothing of earlier mockumentaries like Take the Money and Run and Men of Crisis ; he’d use them again in Husbands and Wives and Sweet and Lowdown). The split-screen sequences — one for Harry and Sally’s Casablanca­-viewing goodnight phone call, one when they call Jess and Marie after “doing it” — echo the split-screen psychotherapy scene in Annie Hall. Meg Ryan’s Midwestern innocent not only reminds us of Diane Keaton’s Annie, but there’s actually a scene where she sports a men’s suit ensemble and an Annie-ish hat. Allen’s protagonists (usually played by himself) made comic hay of their obsession with death; Billy Crystal’s Harry is so consumed by the subject (“I spend hours, I spend days” thinking about it, he insists) that he reads the last page of a book first so he knows how it ends, on the off-chance he’ll die before completing it. Ephron’s Manhattanites are well-to-do brownstone dwellers, magazine writers, and political consultants, much like the insulated Upper East Siders of Allen’s ‘80s comedies. And the picture ends on New Year’s Eve, just like Allen’s 1987 film Radio Days.

A few critics, at the time of When Harry Met Sally’s release in August of 1989, noted the whiff of Woody — chief among them The New York Times’ Caryn James, who called it “the most blatant bow from one director to another since Mr. Allen imitated Ingmar Bergman in Interiors” and dismissed it as “the sitcom version of a Woody Allen film, full of amusing lines and scenes, all infused with an uncomfortable sense of déjà vu.”

But most of the reviews were rapturous, and moviegoers came in droves; though never the #1 film at the box office, it grossed $92 million and was the 11th-highest-grossing movie of the year. Allen had never put up numbers like that, and still hasn’t; his highest-grossing movie to date had been Hannah and Her Sisters three years earlier, which brought in $40 million. (Adjusted for inflation, Annie Hall and Manhattan made $140 million and $132 million, respectively — but by the same adjustment, Harry kicks up to $186 million.) For comparison’s sake, his 1989 film, Crimes and Misdemeanors, topped out at $18 million.

But that comparison is also artistically instructive. By 1989, Allen had quietly backed away from the kind of chatty New York rom-com that had become his specialty; he’d spent the last two years making challenging (some said dull) chamber dramas, and Crimes was a fusion of his dramatic and comic sensibilities, though even its “funny” half was a good deal darker than the likes of Manhattan. Reiner and Ephron may simply have had better timing than Allen, who was always a little bit ahead of his time, and made a “Woody Allen movie” at a time when that term was in flux. They also may have had a more conventionally acceptable leading man, in the looks-driven 1980s, than Allen, whose comic persona and kvetching style had, by this point, put more casual viewers off.

Yet the key to When Harry Met Sally’s initial financial success and subsequent cultural ubiquity most likely lies in its third act, when it takes some turns decidedly its own. To be clear, it’s not all an Allen carbon copy; the famous Katz’s Deli sequence, for example, is a funny scene, but it’s also a “funny scene,” an entirely unbelievable set piece with a (hilarious, mind you) sitcom punchline that one can’t imagine within Allen’s more grounded world. But most strikingly, once Harry and Sally take the plunge and their relationship becomes more serious, it becomes more of a conventional romance — and more of what we would come to define as an Ephron movie.

Most importantly, the picture culminates with an apologetic Harry coming to his senses, sprinting through New York City on New Year’s Eve, and delivering a big, heartfelt speech so he can win back Sally, who he really loves after all. This happy ending is When Harry Met Sally’s chief divergence from the Allen playbook. It’s not just that his best-known comic romances, Annie Hall and Manhattan, end with their focal couples apart rather than together; in Allen’s nearly 50 films as writer/director, only six (Zelig, Broadway Danny Rose, Hannah and Her Sisters, Oedipus Wrecks, Curse of the Jade Scorpion, and Melinda and Melinda) feature a couple that meets, falls in love, and lives happily ever after.

Allen’s jaded view of love — all broken relationships and heedless infidelity — may be the more realistic one, but realism don’t sell tickets, kids. Though filled with echoes, homages, and outright rip-offs, When Harry Met Sally would come to be seen as a true original, setting the template for decades of Meg Ryan, Julia Roberts, and Katherine Heigl vehicles from directors like Nancy Meyers, Garry Marshall, and Ephron herself. Yet it also proved prescient for Ephron’s career as a filmmaker; she would only find real movie success, critically and/or commercially, in these kinds of loose adaptations, like the Affair to Remember­-inspired Sleepless in Seattle or the Shop Around the Corner riff You’ve Got Mail. Her other films were, um, somewhat less noteworthy. (Ever sit through Mixed Nuts? Michael? Hanging Up? Good heavens.) When Harry Met Sally… remains a funny, charming, sophisticated comedy, burbling with wit and flying off the considerable chemistry of Crystal and Ryan. But the more time you spend with its unacknowledged sources, the more it feels like the work of a particularly good cover band.