Today! Because he was very jealous, and I had these days of the week underpants –
When Harry Met Sally… (1989)
Directed by Rob Reiner (x3)
Starring Billy Crystal (x2), Meg Ryan, Bruno Kirby (x2), Carrie Fisher (x4), Steven Ford, Lisa Jane Persky, Michelle Nicastro, Kevin Rooney, Tracy Reiner (x2), Estelle Reiner
I like to think that my personal preference on this list is mine and mine alone, that maybe there were influences over the years steering me toward certain things, away from others, or just jamming something I might not have otherwise seen in front of my face for endless years until it lodged in my brain as something I really enjoyed. As you might have noticed, various of my family members had this effect on me growing up – with their Ghosts and She Wore a Yellow Ribbons and Rocky Horror Picture Shows. However, today, we come to my wife’s favorite movie, somehow, at number 151. Remarkable!
In all fairness, I’d seen When Harry Met Sally a bunch of times before we met in 2004 – it’s kind of every girl you date’s favorite movie, at one period in time or another – but it also aired endlessly on TV at just the right time for me, like 1990 to 1993, when I knew Billy Crystal best from Saturday Night Live and as the host of the Oscars. And maybe I didn’t pay it a ton of mind then – it is firmly a romantic comedy, with many of the typical romantic comedy beats, that would not appeal to pre-teen Joe – over the years and the many viewings, I’d come to appreciate just how excellently it carries out that rom-com plot, to the point that it largely makes the standard genre fare almost unbearable (again, for a guy, with not a ton of interest in this manner of film).
Really, why is it these movies appeal so directly and damn near exclusively to women? That doesn’t seem fair. Romance is for everyone out in the real world – so why aren’t these movies more popular to dudes? Do they just need to tweak that formula a little? Is it the marketing? I mean, there is some tiny love story in pretty much every movie made, so it’s not like guys can’t stand seeing anybody get attracted to anybody else without storming out of the theater. I’m now worried that maybe I’ve ignored this whole giant set of films virtually my entire life because I figured I wouldn’t like them, and that was completely unfounded bias based on nothing but gender stereotypes. I mean, hell, When Harry Met Sally is hilarious, and works damn near perfectly as a movie and as a romance. Sure, it seems more clever than your average will-they-or-won’t-they, but maybe it’s not. Maybe they’re all like this!

Seriously, is this movie awesome? Even with that expository a title, I have no idea what this is about
That can’t be true. While the inventive plotting and funny script by Nora Ephron are excellent, the other main thing going for this movie is that it is almost entirely Crystal and Ryan, and Kirby and Fisher – there aren’t really even other characters. Lots of glancing cameos, including Reiner’s mother Estelle with the most famous line in the movie, but it lets the stars do the heavy lifting and it comes off wonderfully. There’s not one meh performance in the group – unlike, say, your Valentine’s Days or your Love Actuallys. Maybe it’s just giant cast romantic comedies I don’t care for.
But yes, while Sarah does not enjoy many of the films on this list, her top movie made it all the way to #151! Good for you, boots! It picked up an Original Screenplay nomination at the Oscars, but fared better at the Globes, nominated for Best Picture Comedy or Musical, Best Director, Actor, Actress, and Screenplay – it ran square into eventual Oscar winner for Best Picture Driving Miss Daisy, though, which won all the Comedy/Musical awards here. Ephron did pick up a BAFTA for the screenplay, though! No awards were given for Best Oklahoma Karaoke in Front of Ira, however!
Rob Reiner becomes the 15th Three-Timer in the director wing, following The Princess Bride and A Few Good Men, while the immortal Carrie Fisher advances as the 11th actress in the Four-Timers acting guild, with appearances in Soapdish, Jay and Silent Bob Strike Back, and Hannah and Her Sisters. Spotlight!
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