A review requested by flame_boy, with thanks to supporting Alternate Ending as a donor through Patreon.

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There are many charms to Sleepless in Seattle, but also a decent number of annoyances, and I hope you'll all forgive me if I just have to lead with the one that has been pissing me off since before I ever saw the movie, basically for the whole of the quarter-century it has existed: it is deeply invested in "men do this, but women do this" style gags of the hoariest sort. Which is true of a lot of movies, obviously, but in this case it does it right in my backyard: see, women, according to Sleepless in Seattle, weep like leaky fire hydrants at An Affair to Remember, the 1957 melodrama classic starring Cary Grant and Deborah Kerr from 20th Century Fox,* and they do this because they sublimate all of their emotional experiences through the framework of watching corny movies. Men, meanwhile, find this alarming, and watch things like The Dirty Dozen, a violent 1967 war movie, and experience no emotion at all, and indeed mock the notion that one might have an emotional relationship to cinema. As a male who has cried at both melodramas and violent war movies, I find this infuriatingly insulting and reductive to these two films specifically, and to the way that audiences use movies generally, and it gets at the thing that Sleepless in Seattle does with a rather free hand, which is to create two large, disconnected bins, one of them labeled "Girl Shit" and one labeled "Guy Shit", and toss everything including the cities of Seattle and Baltimore into those bins, and then ask Meg Ryan and Tom Hanks to stand in as their embodiments.

This is a disappointing step down from Nora Ephron, who just four years prior as the screenwriter of the great When Harry Met Sally... managed to flirt with this exact binary, but ended up making Harry and Sally (the latter played by the same Meg Ryan, no less!) so very particular and individualised in their personalities and neuroses that they are always first and above all themselves, not stand-ins for Every (Middle-Class White College-Educated) Man and Every (MCWCE) Woman, and Sleepless in Seattle, Ephron's second film as director, seems to actively court that. Which would maybe be less frustrating if Sleepless in Seattle, a gigantic Zeitgeist hit, one that essentially cemented into place all of the rules for the romantic comedy of the 1990s (which maintained itself, with very slight tweaks, as the romantic comedy of the 2000s) that When Harry Met Sally... and the even earlier Annie Hall had left as mere suggestions. It is no exaggeration at all to say that the next 17 years of romcoms were all just Sleepless in Seattle in different clothes; its sins as well as its strengths.

And aye, yes, there are certainly strengths, the biggest of them being that it stars Meg Ryan and Tom Hanks. This was the second of their three collaborations, and in some ways the best - certainly the most important. 1990's Joe Versus the Volcano is a phenomenal object and one of the great under-appreciated films of its decade, but it's pure delirium. 1998's You've Got Mail is charmless sludge. That leaves this film and this film alone as the expression of the two actors' skills at light comedy being done as efficiently and crisply as can be managed. Not their chemistry; in fact, they barely appear onscreen together at all. But they pair well even so, finding complimentary rhythms that help sell the film's conceit that these people are soulmates from all the way across the country. Oh, right, the plot: Sam Baldwin (Hanks) has a dead wife (Cary Lowell), and to flee his pain has moved all the way from Chicago to Seattle. A year and a half later, his precocious son Jonah (Ross Malinger) calls a nationally-syndicated radio advice show on a lonely Christmas Eve to tell the world that his dad needs a new girlfriend, and Annie Reed (Ryan), a Baltimore news reporter, grows from finding this to be a cute story to an all-consuming sign that her engagement to the very sturdy, very square Walter (Bill Pullman) isn't doing it for her. Eventually, she uses all the powers of the American news industry to stalk him, while she thinks she's writing him letters (actually, it's Jonah) that sets up a meeting atop the Empire State Building, just exactly like in An Affair to Remember. As this happens, Sam rather inconveniently desires to be left alone in his sullen depression.

So yeah, thoroughly contrived, and with a foggy confusion over where "cute and endearing" ends and "legally actionable behavior that is the sign of borderline personality disorder" begins - the bread and butter of '90s romcoms, really. What makes this all work is substantially on the performers, much more so Ryan than Hanks; he's transparently looking forward to making serious dramas (Philadelphia, Forrest Gump, and Apollo 13 would prove to be his next three vehicles after this), and he's definitely playing up the "emotionally deadened widower unable to think of anything but the face of his soulmate, rotting in the ground" angle rather than the "cute lead in a flighty comedy" angle. This, at the very least, destablises the film. But Ryan, now she's just superb, mellowing out but not eliminating the acrid neuroses she brought to When Harry Met Sally... and pretty nearly matching her performance in that film, albeit in a role that probably demands less. Still, Annie is the much more interesting character, with the much more obvious pitfall: Sam just has a dead wife, but Annie has a live fiancé, and Sleepless in Seattle is early enough in the '90s/'00s romcom cycle that Walter isn't being painted as an obvious nightmare. He's a nice, albeit boring man, and Ryan has to navigate the arc of making it clear why Annie doesn't actually love him without killing off our sympathy for her, playing the role essentially as an act of constantly overhearing herself and realising how much she's settling, being constantly surprised and shocked at herself for settling, and she has to do all of this in the context of a film that wants to have the champagne-bubble lightness of a pure fantasy with hardly any heavy emotions in its head (this is a film in which many people cry many times, and except for Sam mourning his wife, we're never once meant to cry along). It's a weird, complex role with a lot of moving parts, and Ryan glides across it like a champion ice skater who'd never dream of letting us see her sweat.

Surrounding the two of them is a pretty altogether terrific cast of supporting characters, including Rosie O'Donnell in her absolute best-ever film role, and David Hyde Pierce stealing the hell out of his only big scene, just months before Frasier made him a star. Ephron's instincts at a writer thread a relatively fine path between broad-as-a-barn sitcom laugh lines and some pretty sharp, biting representations of people just a bit too self-aware for their own good, and the human population of Sleepless in Seattle is well-etched, if sometimes a bit too easily slotted into obvious plot functions, or designed to make the battle of the sexes material even louder and more one-note. Mostly, though, they provide just the right colorful backdrop for Sam and Annie to work through their own hang-ups and display their respective worldviews for our amusement and elucidation.

The result is a perfectly charming little movie, graced by the lightest of directorial hands - Ephron allows scenes to play out with an ambling, unforced rhythm that very much helps to keep the increasingly contrived development of the plot feel organic, even necessary - and the sense of lightness added by a whole lot of comic actors making things look easy and tossed-off even when they're precisely controlled (except for Hanks, who very much lets us see the work). It's a less-than version of When Harry Met Sally... in pretty much every way, from its more toothless characters, to its shtickier plot, to its more desperate reliance on a trite soundtrack of quasi-sophisticated standards. And yet, it's substantially better, funnier, smarter, and more impeccably-controlled than almost everything that came in its wake. It's a very amiable film, and while it's easy to want more out of anything, even a bright comedy, than simple amiability, one should never pretend that it doesn't take focused talent to make something this effortlessly pleasant.

*A film inferior in all the ways I care about to its 1939 model, Love Affair, and to top it off, everybody who watches it, watches pan-and-scan copies on TV, therefore killing its most interesting element, the early CinemaScope compositions. But there is no argument made that any of these people are cinephiles, and I shall therefore let it pass.