So much of this is enlivened by casting. Billy Crystal brings his rapid fire deadpan standup style to Harry. His dead-eyed assertion that there can be no genuine friendship between men and women, the proposition that fuels the plot and that uncertainty abovementioned, is handed to the audience like an entry token. Meg Ryan's explosive rejection of it takes her character from the rude keynote moment of breaking up a kiss with a barmp of a car horn to the completing antagonist role. While Bruno Kirby's idealist friend of Harry is mostly little more than a soundboard for Harry's quipping, he does emerge with some integrity (not easy, given his screen mates).
For me, though, it's the thankless and stellar turn by Carrie Fisher as Kirby's counterpart who only ever shines. Her role is better written and might well be Ephron's autobiographical sketch. Marie is a mentor who, in those days prior to the introduction of a mini cosmos on a screen, carries a card index of eligible men (and needs, now and then, reminders to perform data clean-up while at lunch). Fisher's eyes absorb every single thing they see and calculate its value in nanoseconds. This is warmed up with some New York sass and makes me wince that she wasn't in more comedy, rising to writing like this and showing herself naturally funny in person.
As I followed the progress of this film on rewatch (the first since I saw it all them years ago) I was struck by how slow it felt. It's barely past the ninety minute mark but feels much longer. It's never less than engaging but its structure depends on the audience's tolerance of continual circling back to square one with a diminishing return. While this is appreciable as a narrative attack after the credits roll, at the time it can feel draggy. When fresh, there was little pushback when calling When Harry Met Sally Woody Allen lite. As Woody Allen had reinvented the rom com with Annie Hall over a decade before, there had been a strain of them in the interim that had attempted the same but, unless you really know what you're doing, most attempts are doomed. This works because it rolls back the harder edges of the Allen movie and keeps things soft all the way through.
The swearing in the dialogue, while not remarkably new, is used so judiciously it lands percussively every time but then it's a cue to roll another restaged old couple moment and everything smooths back down. Seeing this again, I was reminded of another late '80s revisit in Broadcast News which got everything wrong in its attempt to rekindle the bottled lightning of Network, making what was edgy cute. Harry Met Sally doesn't fail the way that one did, but it doesn't reach further, either. It's what a lot of culture felt like in the era as the tougher and more inventive approach were absorbed into the mainstream for easy digestion. The '90s would bring disruptors like Hal Hartley whose arthouse rom coms played like punk records and Tarantino whose homages to '70s kitsch felt more violent and funny than their source points. With this filtration and the nosedive of Woody Allen's reputation, Rob Reiner's classic remains a classic in the sense that any popular karaoke number remains, defanged and subject to copying error.
When Harry Met Sally is still a fun and funny movie with a wealth of good talking points for coffee afterwards. I personally think that, although the Allenish echoes in the Louis Armstrong needledrops and authentico interviews give it a softening sense of quirk, the better comparison is the younger relationship in The Graduate which is rich with brash disruption. 1989 was not prepared to dig in to heavy fun with the genre, so we got this exercise in charm instead of a barnstormer. It's why both film and the people it characterises feel a lot older than the '60s movie. The certificate of enjoyability this movies comes with looks shiny rather than fresh ... but is that such a bad thing when it is still funny?
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