I love watching classic movies I’ve never seen before.

I don’t always love the movies themselves–at least not as much as I’m “supposed” to–(though I often do), but I love taking the way back machine and checking out something I’d long-since missed.

I get “You’ve never seen [beloved film]?!” somewhat often despite the fact that I’ve seen… just… so many movies. There are still so many out there to watch! And I’m working on it! It just takes time.

For today, for instance, we finally got around to the 1989 Rob Reiner classic, When Harry Met Sally. I was, I think, eight years old when this film released, and so it would have not been in my orbit of interest at that age because it featured neither the Teenage Mutant Ninja Turtles nor Jason Voorhees. And by the time I started appreciating more films, I was into a different genre. If I had seen this in the 90’s, I’d not have dug it. So I’m glad I waited.

When Harry Met Sally is the tale of two people played by Billy Crystal and Meg Ryan (I’ll bet you can figure out their characters’ names) who meet once in college as they embark on the eighteen hour drive from Chicago to New York together. At the time, Harry is dating Sally’s friend, so there is nothing between them. Sally finds Harry boorish and elitist; Harry is attracted to Sally, but seems a bit judgmental about her nuances.

Years would pass after they both arrive in New York, and they would not meet again until they bump into each other in an airport. They sit together on the plane, and they still rub each other the wrong way. And, again, that would be that for another few years.

Finally, as adults both leaving painful relationships, Harry and Sally meet again, and this time, the seeds of friendship bloom between them. They become an inseparable pair. We see them grow as friends over the course of the rest of the film as we are left wondering… can a man and a woman really be just platonic friends?

TWO UPS AND TWO DOWNS

+ Crystal’s comedic wit and rapid-fire delivery. Ryan’s adorable charm and fierce independence. It’s about as top-tier of a cinematic pairing as you are likely to find. They feel so seamless together, and I don’t know if that’s because they truly are or if it’s because years of hearing about this movie just makes me assume it’s true. But they just feel like they belong on screen together. Have they done any other pictures together? I know Ryan would end up doing a few with Tom Hanks in the 1990’s, but I can’t think of any other pairings with Crystal. Regardless, their charisma and chemistry carries the flick from beginning to end. 

It’s so rare for a casting director to be able to find a pairing like this. I’m someone who enjoys a good romantic comedy, and I can think of other solid duos (Ryan Gosling and Emma Stone in La La Land and Crazy Stupid Love; Ryan Reynolds and Sandra Bullock in The Proposal), but Crystal and Ryan stand out above them all.

+ The story is well told, and I had no idea that there was basically ten years between the titular meeting and then the true beginning of the friendship. I was taken aback where, after their drive together to New York, the movie showed us “Five Years Later…”, just to give us another quick meeting between them and then another five year skip! I was invested early in the film, and I almost felt… how to word this?… ripped off? Like Harry and Sally were losing time together I expected them to have! Rob Reiner and Nora Ephron really make the whole ordeal feel like fate. They meet; nothing happens. They meet again; nothing happens. They meet yet again; now there are sparks!

And from their friendship comes a flurry of tremendous scenes of the two of them getting closer and closer. Sally’s ability to put up with Harry’s bluntness, and his finding her particularness endearing. Everything about their dynamic just works so well.

– I’m not sure what the interstitials with the older married couples really added to the film other than a few minutes of runtime. If you remove those from the picture–even including the final one of Harry and Sally themselves (which, if they were going to include, really ought to have featured them in old couple make up)–I’m not sure the movie loses anything of note. They’re cute, I guess, but not relevant.

That brings me to the runtime, and I was surprised to see When Harry Met Sally clock in at just over ninety minutes. I would have imagined this was longer than that. And can I be frank? I might have appreciated it if it were. The stuff about their friendship is so good, and there is so much to be relished… I could have stood fifteen more minutes of them just being together before the third act drama unfolds.

I don’t often report that a film should have been longer, but one that is as well made and entertaining as this one was could have been.  

– For a movie that is pretty much THE RomCom of all time, I thought it was relatively light on there Comedy aspect of things. I’m not sure I really laughed at anything going on. Crystal’s delivery, as noted above, is tight and fast, but I don’t think it elicited much more than a chuckle from me. Don’t get me wrong: the Rom really works! But the Com was lacking. 

I’m going to refer back one more time to The Proposal starring Reynolds and Bullock. While I’m not saying that film is superior to When Harry Met Sally (I scored The Proposal a half star lower on Letterboxd), it did make me laugh more than this one did. It had the Com aspect in full effect. I just wish I’d had the same reaction to Harry and Sally.

OVERALL

When Harry Met Sally deserves all of the great things you have heard about it, and maybe more. It is THE RomCom for a reason. Bily Crystal and Meg Ryan shine like the brightest stars in the night in their outings here, and every RomCom that came after this has been chasing that level of chemistry from its leads. What a wonderful viewing this was.