There are, in the broadest possible sense, two epochs of the English-language romantic comedy. One was the age of the great screwball comedies, which ended during World War II. The second was the era of of the cosmopolitan (i.e. New York-based, or occasionally Los Angeles) romcom about neurotics, which started in 1977 with Woody Allen's Annie Hall, and ended sometime in the first decade of the 21st Century, recently enough that I cannot swear when it ended, though I imagine few people would disagree with me that the days of Sleepless in Seattle, How to Lose a Guy in 10 Days, and Hitch are over now.
There's one important difference between these two traditions of the romcom: the ones from the 1930s were almost always extremely good, and were frequently masterpieces. The ones from the '80s, '90s, and early '00s were almost always mediocre. "Almost", but not "always". At least four times, the contemporary romcom form produced a film that could stand head-and-shoulders with any of the genre's leading lights from the golden age. One of these was Annie Hall itself, which cheated its way there by virtue of being a florid structural experiment about the nature of memory, edited from the ruins of a failed murder mystery. The second and third, 1984's Romancing the Stone and another Allen film, 1985's The Purple Rose of Cairo, are genre hybrids with action-adventure and fantasy, respectively. That leaves only one altogether "pure" romantic comedy from the last 40 years that is an outright masterpiece of romance, comedy, and cinema itself: the great New Year's Eve movie from the legendary summer of 1989, Rob Reiner's film of a Nora Ephron screenplay, When Harry Met Sally... It is, according to every angle I can scrounge up, a perfect movie, save for one somewhat minor annoyance: the black-on-white opening credits, set to a light-jazz version of "Our Love Is Here to Stay", are the most banal way possible to play at being Allen Lite, and the film refuses thereafter to ever bring in any piece of music that doesn't similarly evoke a department store playlist designed to appeal to conservative grandparents.
But outside of that? The film gets pretty much every solitary thing right all the way down to the finest possible details, like that suggestive little ellipsis. For that's the whole movie, right there: in 1977, when they were both recent graduates from the University of Chicago, Harry Burns (Billy Crystal) met Sally Albright (Meg Ryan), and... then the movie and everything else spins off from it. They drive from Chicago to New York (ooh, that's something else the film gets wrong: the shot down Lake Shore Drive from the north side that movies set in Chicago love is incompatible with a starting point at UChicago; I believe, but do not know, that it similarly fudges New York), and Harry is a rude sexist asshole while Sally high-strung to the point of dysfunction. They don't see each other again until 1982, when they bump into each other in an airport, and while he is marginally less obnoxious, they still barely manage to tolerate each other. And then it's another five years until 1987, when they're both in their early 30s and halfway stable people for once, if you don't count the awful breakups they've both just suffered, and this is the point where those meet-anti-cutes start to pay off: having already shared with each other, perhaps uncomfortably, their respective views on sex and relationships, the two attempt to disprove Harry's youthfully arrogant prescription that men and women can't ever be platonic friends, because the man's desire for sex will always get in the way.
Spoiler alert for a 28-year-old generational touchstone: it turns out they can't, and if there's one thing about When Harry Met Sally... that personally offends me, it's that message. On the other hand, the original drafts of Ephron's screenplay ended up leaving the pair romantically uninvolved friends at the end, and I will certainly admit that would have been completely unacceptable. Fuck real life: obviously we want Harry and Sally to end up together, because that is what romantic comedies do. They slam two people together in heteronormative pair-bonded bliss, regardless of whether it would be good for them or not, because it is enormously pleasurable and wish-fulfilling to watch. In the case of this particular movie, it's all the more satisfying, because unlike so many other romcoms, there's no idiotic 11th-hour threat to their happiness, nor a cartoonishly awful Other Man/Woman; there's just two people with a lot of defense mechanisms who need to learn how to get the hell out of their own way, and that is the thing we watch them do over the course of 96 minutes.
That's another thing it does right, by the way. Comedies that weren't too long were more common in the 1980s than now, but even granting that, When Harry Met Sally... is a tightly-plotted and beautifully waste-free motion picture. This, I think, is one of the two great things it learned from the 1930s romantic comedies: take the time you need and then stop. The other thing was to make the film about both members of the couple, not just one or the other; even Annie Hall, which I treasure like few other movies, is clearly told exclusively from Alvy's perspective. When Harry Met Sally... starts out favoring Sally, both in the way that Reiner and cinematographer Barry Sonnenfeld position her within the frame (the end of the 1982 sequence, which leaves Ryan in medium-close shot while letting Crystal fall into the back of the frame and out of focus, is the clearest tell; so are the extremely tight close-ups on her face as Sally recognises Harry before he recognises her), and in how unapologetically unlikable that Ephron, Reiner, and Crystal allow Harry to be in the first two segments.
But when it arrives in 1987 and the story really kicks in, the film scrupulously gives both leads plenty of space to be the lead, together and in their own isolated scenes. The result is a marvel and a wonder, the most egalitarian of romantic comedies, or even romantic movies, period, in the last half-century: the result is the best character Ryan ever played and accordingly her best performance as one of the great female leads in any comedy from any era (Crystal, who's playing a distinct variant on the Woody Allen Character - New Yorker, Jewish, morbid sense of humor - is probably equally as great, but feels less fresh). The same "it's about both of them" approach pops up in Ryan's two other major romantic comedies of the following decade, Sleepless in Seattle and 1998's You've Got Mail (both of them directed by Ephron from her own scripts) neither of which has the precision of character writing of When Harry Met Sally..., both of which are much more comfortable with cozy sitcom-level concepts, and therefore neither of which emerges as nearly so great an achievement.
There's hardly anything that could be called "sitcom-level" about this movie (really, only the one "punchline"-type gag is the famed "I'll have what she's having", which is such a perfect capper to a marvelous scene that it's worth forgiving). On the contrary, this is a remarkably smart, adult movie, with two very self-aware characters discussing themselves and their worldviews in conversations that feel uniformly honest to their personalities. Ephron's script is outstanding, and a deserved Oscar nominee (the film's only one, though it easily should have gotten nods for Ryan and Carrie Fisher, brilliant as the acerbic best friend, and there are another four at least it could have earned in a world with less institutional bias against comedies). Not just for the lines, which are often golden - also for the impressive parallel structures silently threaded in, like the stark contrast between Christmas in 1987 and 1988 (one about good friends pulling for each other, one about the misery of singlehood in your 30s in New York), or the way that the two different scenes where the female sex drives is discussed in a restaurant showcase the dramatic difference between how a man and a woman physically perceive sex. But When Harry Met Sally... isn't only about its writing, however whip-smart that might be. It's an astonishingly well-made film, with Reiner and co. treating it like, get this, a piece of visual storytelling and not just a machine for dispensing jokes. Sometimes, they even augment and strengthen those jokes through careful manipulation of film language. What a remarkable concept!
But for real, it is an impressively made film, all right. It was edited by a certain Robert Leighton, who was also responsible just before for cutting Bull Durham and Reiner's The Princess Bride, which should between the three of them be enough to argue that he was maybe the best comedy editor of the 1980s. In the case of When Harry Met Sally..., most of that great cutting shows up in small ways that have nothing to do with the big showy gestures, like the split-screen bedtime conversation about Casablanca (which is a great gesture, certainly: connecting the characters in their isolation, and quietly insisting that we think of them in bed together), but in the small things like how Harry and Sally share a bemused shot-reverse shot reaction as their best friends Marie (Fisher) and Jess (Bruno Kirby) fall in love with each other and talk loudly while we watch the leads instead. Or sometimes, it's just about selling a joke by putting in a little tiny pause for the punchline and then quickly moving on to make the moment feel harder-hitting. And it's not just well-edited: Sonnefeld, just a year away from Miller's Crossing, shot one of the most beautiful comedies in a whole generation (in fact, he shot two: Raising Arizona was just a couple of years in his past. And for that matter, there's a lot to find dubious about Throw Momma from the Train, one of the films he shot in between the two, but it's well-shot). New York in autumn has a feverish, golden glow, but not one that feels fake or over-the-top; it's simply a beautiful way of looking at a city that usually gets more of a grimy, grainy treatment, and providing a striking backdrop of pure visual romance for the two characters who need to be goaded that way - literally, in a heart-to-heart that positions Harry and Sally as mostly black silhouettes in front of a window with Central Park flaming in red and orange behind them.
So it is, all told, an outstanding film, correct in all the ways that matter, utterly precise in how it depicts at least its four biggest roles (Jess takes longer to crystalise than Marie - who is already perfectly formed in her first scene, when she folds, rather than tears up, a card for a married man in her rolodex of prospective romantic partners - but by the end he's as sharply etched as she is), full of great laugh lines that are also piercing character moments: "I'm gonna be forty!" "When?" "...someday!" In two paired scenes, it's maybe the all-time best screen depiction of the hope and promise, as well as the boundless possibility for frustration, of the countdown to midnight at New Year's Eve. It's just... so good. If there's been a better American movie about the specifically gendered way romance works in all the years since, I can't name it, nor if there's been a funnier movie about intellectual neurotics in the same time. It's smart and beautiful and mechanically flawless, and it single-handedly redeems all of the subsequent history of movies trying and failing to capture a portion of its genius.