When Harry Met Sally... (1989)

Director: Rob Reiner

Cast: Billy Crystal, Meg Ryan, Carrie Fisher, Bruno Kirby

Have I Seen it Before: Oh, sure.

Did I Like It: And that may be part of the—completely subjective, not at all the fault of the film’s—problem. I haven’t seen it in years. Lora and I were even talking about it while we were watching it, and I’m not entirely sure she and I have ever watched it together in the sixteen years we’ve known each other. Lora seems to think we have, but I’m really not that sure.

The film always seems like—with its trips to The Sharper Image where one can act like they invented karaoke, deep connections over the same movie playing on TV*, and a sweater or two—a time capsule.

It’s also an emotional time capsule, though. If you’re not trapped in a decade-long cycle of will-they/won’t-they, does it play the same? Say, if you’re somehow more like Marie (Fisher) and Jess (Kirby) and despite some troubles have largely settled that part of your life, does the dithering and navel gazing of Harry (Crystal) and Sally (Ryan) still hold any meaning after all these years?

It’s probably a better question than that old, hoary cliché of wondering whether or not Harry and Sally are still together in the ensuing years, but not an entirely unrelated one. I tend to think that if the two protagonists didn’t come to some kind of peace about themselves, the quirks that caused them to come together in a fit of romantic whimsy would probably come back around to make them run for the hills.

But then, if my mind can’t help but go to these kind of quibbles, is it possible the entire genre of the romantic comedy has completely lost its meaning? That’s possible, and would still allow this film to keep its crown as the superlative entry in the genre.

*Given that might, in fact, be a method of connecting over movies that has reached essential extinction, the moment where Harry and Sally disassemble the ending of Casablanca (1942)  hits a bit harder than anything else.

Innerspace (1987)

Director: Joe Dante

Cast: Dennis Quaid, Martin Short, Meg Ryan, Kevin McCarthy

Have I Seen it Before: Oh, sure. I might have been compelled to include this in the reviews much earlier, as it was playing during the marathon of movies where I got to meet Dante*. As it came fresh off the now infamous summer of 2023 blackout, I opted to go home before it started to sleep in an air conditioned bed for the first time in over a week. Alas.

Did I Like It: There are movies Joe Dante directs where he is allowed (or maybe he stole?) free reign to do whatever he wanted, then there are those movies where he is hired to do a job, and inevitably does a yeoman’s job. Oddly enough, this one falls somewhere in the middle, which has a certain refreshing quality to it. At it’s core, it’s not much more than a slightly modernized riff on Fantastic Voyage (1966), which is interesting enough. The script justifies itself by forging together an odd couple out of all-American Quaid (how has he never played Jonathan Kent, when his son has already played Superman?) and comic goofball Short. Their chemistry fuel the movie almost entirely, made all the more impressive that the two stars barely share a few minutes of screen time physically, shifting the pitch on this film from an Odd Couple meets Fantastic Voyage to a high-concept comedy version of Star Trek II: The Wrath of Khan (1982). Throw in some Looney Tunes-fueled high energy sequences, and you’ve got perhaps not Dante’s greatest film, but certainly one worth a watch all the same.

*I told him that Gremlins 2: The New Batch (1990) and Matinee (1993) were two of my favorite films. He politely thanked me, but there was an undercurrent to the thanks that—perhaps appropriately so—wished I had seen more movies. Alas.

Sleepless in Seattle (1993)

Director: Nora Ephron

Cast: Tom Hanks, Meg Ryan, Bill Pullman, Ross Malinger

Have I Seen it Before: Oh, sure. Not as many times as You’ve Got Mail (1998), certainly, and I have to admit the moment that sticks in my head more completely than any others is the exchange about one of the letter writers is Sam’s (Hanks) third grade teacher, but that’s only because that scene is in The Cable Guy (1996), and I’ve seen that film quite a bit.

Did I Like It: Here’s a statement that I didn’t think I was going to write when I started rewatching the movie, but it is a conclusion I can’t escape:

Sleepless in Seattle is the Star Trek II: The Wrath of Khan (1982) of romantic comedies.

Wait, don’t go. Let me explain.

This isn’t necessarily a measure of quality. Sleepless is fine, I have no complaints, but if we remember from earlier, I’m more of a You’ve Got Mail man, myself, and it isn’t just because of the typewriters, because there’s more than a little typewriter porn to be found here. It’s more of a measure of the film’s construction.

Much has been made of the chemistry between Ryan and Hanks. It made Mail one of my absolute favorites, and made Joe Versus the Volcano (1990) a mainstream movie and not one of the weirdest thing to get a wide release.

But they barely share a scene together in this film. They look at each other across a highway, and I wouldn’t be shocked if neither of them where on that stretch of road on the same day. They exchange a few words on the roof of the Empire State Building, and that’s the whole show. Just like Montalbán and Shatner in Khan, when you think about it. Maybe I’m the only one thinking about it. I can acknowledge that.

You’ve Got Mail (1998)

Director: Nora Ephron

Cast: Tom Hanks, Meg Ryan, Parker Posey, Greg Kinnear

Have I Seen it Before: Many, many times. Greg Kinnear’s character might have seeped into my brain a little bit.

Did I Like It: Remember when this movie was released and it seemed like it was a love story for the foreseeable future? Dial up connections, America On-Line, and the impenetrable power of the large bookstore chain.

Now, it’s possibly even more quaint than its ancestors The Shop Around the Corner (1940) and In the Good Old Summertime (1949). A subsequent, more current remake of the film would only work as a horror movie. Which now that I think about it, I need to go make a note in another document… The Greg Kinnear character can still use AOL if it makes everyone feel a sense of unearned of comfort.

On that note, I’m struggling to think of a film more designed to—and succeeds to—comfort from moment to moment. Hanks and Ryan—the end result of a long-dormant government experiment to create beings of pure likability—are at the top of their collective game*, and that’s in a film where demonstrably, Hanks is playing the villain. Imagining a world where everyone from the corporate fat cat to the plucky underdog is fueled entirely by being good with a turn of phrase when they’re not eye-ball deep in a book is more romance than anyone ought to get from a single movie.

And sure, the triumph of true love against odds in a world of increasingly impersonalized communications has its charms, but that ain’t what keeps me coming back to the movie.

*Yep, I’m putting this one ahead of When Harry Met Sally (1989) and Sleepless in Seattle (1993). Come and fight me about Nora Ephron films, if you feel the need.

French Kiss (1995)

Director: Lawrence Kasdan

Cast: Meg Ryan, Kevin Kline, Timothy Hutton, Jean Reno

Have I Seen it Before: …yes? Although as I type this I have virtually no memory for the individual moments for the movie. Maybe I saw it in the middle of it on Cable once? Maybe Lora was in the middle of watching it and I came in on the middle of it.

Did I Like It: I’m a little disappointed when writer-directors (like Kasdan) direct a movie they themselves didn’t write. It feels so mercenary. Is it art? Does a film even need to be art? Anybody who complains about the sameness of movies these days needs to understand that nearly any movie in this genre could be cut together in any haphazard manner, and it would all still kind of make sense. Kevin Kline might speak french intermittently, and Meg Ryan might be really into email and call-in radio shows at random times, but we’d all still have pretty good time.

That probably doesn’t have much to do with this film itself. All of the main players are doing their level-headed mid-90s best. Meg Ryan swings between high strung and adorable like she was put on the planet to do it (which, going by box office receipts alone, she was), and Kevin Kline becomes embodies the contradictions of a leading man and quirky character actor which I… just realized now he peaked in Wild Wild West (1999).

And that’s what most romantic comedies. Cookie cutter plots with people commercially proven to be likable. You can get extra points (possibly even on the back end, if you managed to finagle a producer credit, like Meg Ryan in this particular instance) if you can set the movie in some far flung location that has an aura of romance at its center.

It’s done well, but then again its not hard to do that well. 

Joe Versus The Volcano (1990)

Director: John Patrick Shanley

Cast: Tom Hanks, Meg Ryan, Lloyd Bridges, Robert Stack

Have I Seen it Before: Yes. Although I can’t remember how it all ends, for some reason. That’s probably the best way to rediscover a film, now that I think about it.

Did I Like It: It’s certainly a charmingly weird film, I cannot deny it that. Starting with frames filled with dream-like production design from Bo Welch—hinting at the work he would do in a few years in Batman Returns (1992)—this world is not our own, and yet there are any number of moments that feel distressingly real, although most of those have to do with the horrifying drudgery of Joe’s (Hanks, being imminently Hanksy, even in a slightly off-beat milieu) job.

The secret weapon for the film is Meg Ryan, surprisingly enough. While she has always been a charming presence on film, she’s always felt more like a movie star. Here, she fully embraces the weird on display and very nearly disappears behind two distinct characters, before giving the people who showed up on date night the Meg Ryan we all know with her third character in the film. So few leading ladies are given the opportunity to to flex their craft, it’s one of the film’s stronger elements.

The one element about which I think I might truly bring myself to complain about the film is that the ending is something of an anti-climax. The volcano spits both the leads out, they figure out that Joe hasn’t been dying this whole time, and they sail off into the sunset. That may be why I can’t remember the ending; there isn’t much of one. It is a minor complaint, but might help to explain why the film never quite seeped into our collective thoughts the ways other films with this degree of talent have.