• Director: Rob Reiner
  • Writer: Nora Ephron
  • Starring: Billy Crystal, Meg Ryan, Carrie Fisher, and Bruno Kirby 
  • Accolades: 1 Oscar nomination (Best Original Screenplay)
  • Where to Watch: Watch with subscription on Showtime app, buy or rent on Amazon Video, YouTube, or Apple TV

I recently listened to the Unspooled podcast episode on When Harry Met Sally…, where one of the hosts, just a few years older than me, noted that when he was younger he had “imprinted on this movie like the werewolf from Twilight.” I did not, and in fact just saw this movie for the first time. I liked its basic humanity, its ability to give its characters foibles but not judge them for them. It is, in some ways, covering the same ground as some of the better Woody Allen movies, with less cinematic invention, but also far less baggage. On the hand, there’s something about it that fails to grab me. It avoids tired romantic comedy tropes of having some reason the lead couple don’t get together, which I like, but at the same time that somehow makes the whole thing feel sort of… pointless. They’re going to get together, there aren’t any obstacles to them getting together, yet they’re not because of their own neuroses. I suppose that’s relatable to some of us.

A couple of years ago, I read more than one article with titles like “Who Killed the Romantic Comedy?” The studio romantic comedies just weren’t being made any more, and those that had been most recently were, well, pretty terrible. Some of them involved pre-McConaissance Matthew McConaughey. In the last two or three years there has been something of a resurgence, almost entirely on Netflix, but you’ll still here people say “why don’t they make them like that anymore?” What they mean by “that” is When Harry Met Sally… In some ways it was sort of the first “modern” rom-com, from which sprang a thousand Kate Hudson and Katherine Heigl movies.

Billy Crystal and Meg Ryan (in her breakout role) play the title characters, who first meet when they agree to drive together from college in Chicago to New York, where both are moving. They talk the whole time, he says men and women can never be friends and vaguely makes a pass at her even though she knows his girlfriend. Cut to five years later and they get into a fight on a plane. Cut to five years later and they meet again (in a bookstore that later went out of business because a Barnes & Noble opened down the block, inspiring writer Nora Ephron to write You’ve Got Mail!), and they end up becoming friends. They can talk to each other about anything, despite being so different. They try to set up each other with their respective patented rom-com best friends (hers is played by Princess Leia herself, Carrie Fisher), but the friends fall for each other instead. But will it all be ruined if Harry and Sally sleep together, as they inevitably will?

There are many lines and scenes from this movie that seeped into the general popular culture, some of which I knew came from this movie and some of which I did not. The scene where Meg Ryan fakes an orgasm in the middle of Katz’s Delicatessen is, of course, famous. I get the impression that lots of guys were unaware that women faked orgasms before this. I, being of a different generation, I think initially learned about this from American Pie. And I read the What’s Happening to My Body Book for Boys, and it didn’t mention that. Movies are helpful for some stuff.

The story goes that director Rob Reiner saw Ingmar Bergman’s Scenes From a Marriage and wanted to make a similar “definitive” piece that was originally literally called Scenes From a Friendship. Then he talked to writer Nora Ephron about it and she basically wrote what she thought would work, and the end product is very different. Tom Hanks turned down the role of Harry, and Molly Ringwald was actually cast as Sally when she had to drop out. In the end Meg Ryan won the role. There have been a lot of opinions about Ryan over the years, mostly because she immediately became the face of this sort of role, a thing that a lot of guys seem virulently against for reasons I can’t quite understand. But honestly, my biggest issue is when this movie, or any of her other movies, really, plays with the idea that some guys don’t think she’s attractive. No guys think that.

The soundtrack of When Harry Met Sally… is entirely old standards sung by Harry Connick, Jr., making it feel like it’s set in the same alternate world where modern music never happened as movies like Sleepless in Seattle and Moonstruck. The soundtrack album somewhat inexplicably went double platinum and jumpstarted Connick’s career. I was actually struck by how much the movie owes to its film predecessors. Not only does it get a lot of mileage out of the ending of Casablanca (the argument between Ryan and Crystal about whether Ingrid Bergman wants to stay or go at the end is great, particularly Ryan’s observation that by going Bergman will probably later become “First Lady of Czechoslovakia”), it is full homages and nods to other movies. There are moments when Sally is basically wearing Annie Hall’s wardrobe. The influential telephone scenes, featuring characters talking on barely-denoted split screens, are straight out Doris Day features like Pillow Talk. They turned out sort of the killer app of scenes showing people talking on the phone, the equivalent of the way the BBC Sherlock show suddenly figured out how to do text messages on screen and that’s been how everyone’s done them ever since.

Look, I liked this movie fine. There were several funny jokes, and all of the actors are likable. It’s a very good version of whatever this is. But I have a basic emotional disconnect with the whole thing that it feels like is mostly because of the material. I have said before that one of the many reasons I like movies is because they can be a conduit to empathy with people you otherwise wouldn’t experience. But sometimes there are people I’m not super interested in empathizing with, and I’m not sure Harry and Sally aren’t two of those people. Which isn’t to say I don’t like them, it’s just that they are two people mostly defined by their own neuroses, and I have those already, I don’t need other people’s.

7 thoughts on “WHEN HARRY MET SALLY… (1989)

  1. “There have been a lot of opinions about Ryan over the years, mostly because she immediately became the face of this sort of role, a thing that a lot of guys seem virulently against for reasons I can’t quite understand. ”

    Dude! Guys hate Meg Ryan because she proved without a shred of doubt that women can and do successfully fake orgasms and they are clueless about it. She is literally the face of their own failure.


    1. Haha that is a good point. I think she got a bum rap, but I suppose she’s had a much more successful career than most actresses get.


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