Sleepless in Seattle at 30: Nora Ephron’s Chaste, Strange Affair to Remember

In 2023, it’s entirely possible that the majority of summer movies that make over $100 million at the domestic box office will be considered financial disappointments. But 30 years ago, this was still rarified financial air, and of the five movies to reach those heights, one stuck out for not being a thriller to feature dinosaurs (Jurassic Park), massive movie stars (The Firm; The Fugitive) or both (In the Line of Fire). Yes, Tom Hanks and Meg Ryan were plenty famous when Sleepless in Seattle debuted to positive reviews and delighted audiences, and the movie was tipped early on as a possible summer sleeper. But neither the movie nor its stars were considered a sure thing. Hanks in particular started feeling more like a major star because of his role in the successful romance where people mostly listen to the radio and talk about other romantic movies.

Three decades later, Sleepless in Seattle looks even more anomalous: A chaste and melancholy dramedy that ponders romance more than it actually sends sparks flying in front of our eyes. Hanks plays Sam, an architect smarting from the loss of his wife Maggie, and attempting to muddle through and give his son Jonah (Ross Malinger) a fresh start in Seattle. Jonah, worried about his father, calls a national radio show for advice; the pushy host yanks Sam on the air, and when, against his better judgment, he opens up about his loss, he’s heard by Annie (Meg Ryan) over on the east coast. She’s captivated by his story – smitten, really, although it takes some time for her to admit it, not least because she’s engaged to marry an affable, slightly milquetoast Bill Pullman type (Bill Pullman). As a seemingly self-directed and deadline-light journalist, she decides to do some research on Sam, and eventually/semi-accidentally, despite never directly communicating, they have a rendezvous date: The top of the Empire State Building on Valentine’s Day.

This detail is inspired by the 1957 romance An Affair to Remember, which is both described and excerpted in Nora Ephron’s film. Perhaps surprisingly, director/co-writer Ephron was not responsible for the initial inclusion of An Affair to Remember in the script; that was from original screenwriter Jeff Arch, though Ephron did seem to feel some affection for an otherwise dissimilar writer because she (like Arch’s mother, and apparently not Arch himself) loved that Cary Grant/Deborah Kerr movie. Ephron did write most of the movie’s dialogue, which means she’s likely responsible for both the scenes where characters weepily rhapsodize over the romantic climax of that film, and the moment when Sam and his buddy parody that weepiness by pretending to choke up over The Dirty Dozen. At a time when Quentin Tarantino had only made a single film, Ephron was unleashing multiple movie-recap monologues!

These are some of the funniest and most insightful scenes in the film, locating Seattle as a meta-text about how movies affect our perceptions of real life, particularly romantic relationships. In some ways, An Affair to Remember seems like a mismatch with the actual story of Ephron’s film; in it, Grant and Kerr play characters who meet on a cruise ship when both are otherwise engaged. Despite her initial resistance, their attraction deepens as they learn more about each other, and by the trip’s end they vow to give each other six months to sort out their personal and professional lives before re-presenting their new and improved selves at an Empire State Building meeting. But – as Sleepless in Seattle characters describe, without much context about the movie’s larger story – Kerr’s character gets into an accident and misses the meeting, and is too proud to contact Grant with her newfound disability. (It’s uncertain whether she will ever walk again.) Eventually, he tracks her down, realizes she must now use a wheelchair, and, of course, embraces her anyway.

An Affair to Remember is not particularly about the love-at-first-glance lightning strike that seems to afflict Annie – and Sam, who sees Annie twice without knowing who she is (or that she knows who he is) and feels the same connection. The aspect of Sleepless in Seattle that makes it so unconventional – the fact that its leads aren’t properly introduced until the film’s final moments – is wholly absent from Affair. It’s not a great movie; director Leo McCarey seems to have long tamped down his screwball skill in favor of a lushly appointed melodrama that begins to take on the quality but not the depth of a wallow. But it is a movie where the two leads meet, converse, and work their way towards, essentially, contemplating adultery, such is their grown-up desire. Seattle transmutes that desire into a kind of starstruck wooziness over a ready-made perfect family (the heavy involvement of kids in the plot being, again, sweetly unconventional but also a little weird). For all of its swooniness (and interminable song breaks), Affair is about two people attempting to make themselves worthy of the love they share. Annie and Sam, by contrast, need only to find each other.

Maybe that’s part of the point Ephron is making by leaning so heavily on the older film: Watching our favorite movies, we extract the moments that make us swoon and apply them to largely unrelated situations; maybe, stretching a little further, that’s why Ephron feels so comfortable purloining covers of “As Time Goes By” and “Over the Rainbow,” literally two of the best-loved movie songs of all time, from two massively popular films that have even less to do with this one than the McCarey film. (Then again, maybe Ephron was just one of those Silent Generation members who felt like pop music started to fall off just around the time An Affair to Remember came out.) There’s poignancy, to be sure, in watching Sam grapple with the way that his movie-level bolt-from-the-blue romance has unexpectedly turned into a real-life weepie; in the helplessly heart-melted expressions on Annie’s face when she listens to Sam on the radio; even in the way Annie’s poor Pullman intended reacts to his eventual dumping with grace and good humor – even as you sense that Ephron is tacitly saying that his allergies, his need to sleep with a humidifier, render him vaguely unworthy of cinema-level love.

As an act of reinventing mid-20th-century cinema for the 1990s, Ephron’s Hanks-Ryan reunion You’ve Got Mail is a cleverer riff, this time on 1940’s The Shop Around the Corner (though, to be fair through an unfair comparison, Shop is an all-around greater movie than Affair), and it lets the stars generate actual friction together to boot. Yet as beloved as Mail is, Seattle seems to have the edge in the popular consciousness. It grossed a bit more, despite coming out five years earlier and during a competitive summer movie season; its soundtrack became a bestseller; Ted Lasso recently shouted it out as the superior of the two (a blessing/curse combo if there ever was one). It remains one of the most successful romantic comedies of all time, and fittingly, it’s more the suggestion of a romantic comedy than the genuine article – a feature-length reminiscence of how movies and, very occasionally, real life can make us feel. Understandably, not many movies directly imitate Sleepless in Seattle, because there frankly isn’t much to imitate that would register as particularly romantic, especially now that some of Annie’s behavior plays more like stalking. But many romantic comedies still owe something to the movie anyway; it may not be a great rom-com itself, but it’s a hell of a recruitment video.

Jesse Hassenger is associate movies editor at Paste. He also writes about movies and other pop-culture stuff for a bunch of outlets including Polygon, Inside Hook, Vulture, and SportsAlcohol.com, where he also has a podcast. Following @rockmarooned on Twitter is a great way to find out about what he’s watching or listening to, and which terrifying flavor of Mountain Dew he has most recently consumed.