This is the second in one of two intertwining bi-monthly 2026 series with the same name. The movies in February, April, June, August, October and December involve revisiting my six favorite Rob Reiner films, except for my favorite, This is Spinal Tap,
which I rewatched in conjunction with Spinal Tap II: The End Continues
before the series started.
When I was considering the Rob Reiner movies I'd be revisiting in 2026, I of course came to When Harry Met Sally and thought "Yeah, might as well. I've seen it fairly recently, but it's been a minute so I should see it again."
Nope. It's been more than a minute. In fact, it has been more than 20 years.
I had to double check both of the places I keep track of rewatches, on Letterboxd and in a Microsoft Word document, and true enough, I could not find it in either. I started keeping track of rewatches in July of 2006, so that means that unless I watched this in the immediate few months before I started keeping track, it's been more than 20 years since my last viewing of When Harry Met Sally.
It could not be. It simply could not be.
I feel like I definitely watched it with my wife, and we only started dating at the start of 2005. So probably in that first year together we watched it. But it clearly has not come up for viewing again since then, unless I'm derelict in my records, and I'm rarely derelict.
I'm reminded again that certain movies are so familiar to you -- this would definitely be double digit viewings for the movie overall -- that you feel like you've seen them recently, even when you haven't. Maybe I just couldn't believe that I feel like I clearly remember my last viewing, or at least that such a viewing had taken place, and yet that was at least two decades ago now. Nor could I believe that I wouldn't have been inspired to watch it again in those two decades, just for old times sake.
Well, high time for a viewing of my #26 movie on Flickchart, which has spent a significant amount of time within my top 20. It's crazy to think that I haven't even seen When Harry Met Sally since I started using Flickchart in 2009.
Since I've never written at length about this movie on the blog, I should tell you that I've long considered it to be the greatest romantic comedy of all time. Actually, in the couple times I've written about Reiner himself, I have expressed that opinion. So I don't need to go on at length about it now. (And each time I do express this opinion, I also mention that I understand I am excluding many of the romantic comedies from earlier golden ages of cinema. What can I say, I grew up with When Harry Met Sally -- it came out when I was 15 -- and I didn't grow up with those other movies.)
The other thing I should put on record is that it is also one of my favorite New York movies. I had already been to New York at least once, maybe exactly once, before the movie came out, but this was the movie that likely cemented my impression of Manhattan as an idealized, romantic locale. Actually living there disabused me of some of that notion, but there's still a perfect version of the city that exists within the tight 96 minutes of When Harry Met Sally.
I don't need to spend a lot of time on why the movie works so well, but it's a mixture of the sharp dialogue, the witty performers, the funny scenarios, the keen and sometimes uncompromising wisdoms about relationships between men and women, and the mood-setting jazz piano and crooner music that serves as wallpaper.
I'm willing to bet, though, that the little detail that had the greatest impact on my affection for the movie is the interviews with the old married couples placed sporadically throughout the runtime. I doubt this was actually an innovation by Reiner or by screenwriter Nora Ephron, but it could have been, and it is certainly something that's been imitated since. If I'm connecting Reiner movies, it's a bit of a documentary touch that points back to This Is Spinal Tap, and lends an extra bit of authenticity to everything we're seeing. (And looking forward, Reiner used this tactic in the most recent Reiner movie that I've added to my favorites, The Story of Us.)
Because I know this film so well, I was worried I wouldn't have a lot of new observations on this viewing, so I forced myself to jot down some notes. And as it turned out, there were a handful of things I wanted to mention when writing this post:
1) Did you know this was shot by Barry Sonnenfeld? I did not.
2) I noticed that this movie uses an Ella Fitzgerald song, just as another favorite New York romantic comedy, Kissing Jessica Stein, would do in what I assume was a fairly explicit attempt to remind us of its forbear. Incidentally, I have seen Kissing Jessica Stein three times since the last time I saw When Harry Met Sally.
3) When Billy Crysal is alone, depressed, sitting on the floor in his empty apartment, he's playing a little game of tossing playing cards into a bowl that's about five feet away from him. I never remember noticing this previously, but at one point he lands about five in a row -- a pretty impressive feat.
4) I know that some of Meg Ryan's reactions to Crystal's antics are genuine, and you can really tell when they occur. When he's speaking in his funny voice ("pecan piiiieee"), she gives a real laugh at one point and utters "Oh no." Such a genuine reaction because, well, it was.
5) I really like the scene where Harry and Sally are dancing cheek to cheek on New Year's Eve, and they are spinning around. It's a very clever way for the camera to capture what they are both thinking in that moment, at a moment when they know the other person cannot see their face, and in this case it's a moment of fear about the physical contact prompting them to do something they fear they will regret. The movie is full of these little mirrored moments, such as when they both make an awkward expression during the social gathering where they play Pictionary, upon seeing the other kiss their current paramour.
6) I noticed there's a scene where Sally puts on a pith helmet, I believe it's while they're at the Sharper Image, about to be encountered by Helen and Ira. Reiner would also use a pith helmet for Michelle Pfeiffer's character in The Story of Us.
7) Speaking of the Pictionary scene, there are a lot of great lines in that scene, including anything related to the phrase "baby fish mouth." However, I was reminded how much I love Bruno Kirby's frustrated line "Draw something resembling anything!"
8) Speaking of mirrored moments, what I will call the "duelling telephone calls" scene is a masterpiece of execution. It's when Kirby's Jess and Carrie Fisher's Marie are asleep, and for some reason each has their own distinct telephone line on their bedside tables. (Will share a house but not a phone number?) Harry calls Jess at the same time Sally calls Marie, and it's the morning after Harry and Sally slept together. The overlapping dialogue in this scene is terrific, as both conversations go forward naturally while being able to interact with each other, as Jess and Marie realize they are having the same call about the same thing, and that they both invited the other to come over for breakfast at the same time -- an invitation they are relieved to find the other has rejected. It's some real Robert Altman stuff in terms of complexity of dialogue.
9) I always remember, when thinking about moments of romantic bliss in my own life -- when you are most keenly aware of its potential opposite -- the lovely exchange afterward between Jess and Marie: "Tell me I will never have to be out there again," she says. "You will never have to be out there again," he returns. It feels especially touching when you consider that both Kirby and Fisher are now gone.
10) Random: I noticed the telephone number on the awning where Sally struggles to buy the Christmas tree by herself, without Harry's help. It's 662-4402. Why is this notable? They almost never put phone numbers in movies that didn't begin with 555. Just another touch of this film's effortless sense of realism.
11) If I want to make a really strange connection, between the great Reiner movie I saw this month and the not-great Reiner movie I saw last month for the other bi-monthly Reiner series, it's the ending lines that are meant to serve as a form of reconciliation between characters. When I wrote last month about Being Charlie, the drug addiction movie about and written by Nick Reiner, I noted that one of the few choices I really liked was the character's decision to end by saying to his father "I don't hate you, Dad" -- the closest that character could come to saying "I love you." Well, this movie ends in a somewhat similar fashion, with Sally saying to Harry "I hate you, I really hate you." Which is also a substitute for "I love you."
12) I noticed in the credits there are songs both by Rodgers and Hart (several) and Rodgers and Hammerstein ("Surrey with the Fringe On Top," from Oklahoma!, which Harry and Sally sing in the Sharper Image). I thought that was an interesting thing to see, fresh off last year's movie that featured all three of these characters, Blue Moon.
These were the only notes I took in the movie, but afterward, when I was looking up other times I mentioned When Harry Met Sally on this blog, I came across this post, and I need to correct the record from it.
In case you don't want to click, it was a post about the poor realism of the way batting cages are depicted in the Pete Davidson movie Big Time Adolescence. In that post I drew a contrast to how batting cages are depicted in When Harry Met Sally, but I didn't get it completely right.
While it's true that there is nothing that occurs in WHMS that is an actual defiance of the way batting cages work, in that post I stated that the pitching machine continues to pitch balls to Jess and Harry even after they have turned to speak to each other. On this viewing, I noted that's not the case.
However, it doesn't necessarily undermine the realism of the movie. In fact, it just means that Jess and Harry took the opportunity of no longer being pitched to to turn and talk to each other. These guys are not cheapskates, but they do value a quarter, and they need to keep shovelling them in to get more pitches. (As Harry says to the young kid when they argue about whose turn it is.) They'd hardly let a bunch of pitches go by just to talk face to face about that time Harry made a woman meow.
Okay, if there could ever be enough When Harry Met Sally, we've reached that point for today.
Next up in this bi-monthly series in June is the current #132 on my Flickchart, Stand by Me -- and it's been a lot more like 30 or even 35 years since I've seen this one.