Twenty-five years ago, When Harry Met Sally revolutionized the romantic comedy. Sure, this film genre had been around since the earliest days of cinema, and had once been the domain of giants like Billy Wilder and Ernst Lubitsch and Stanley Donen. But Rob Reiner and Nora Ephron’s 1989 hit, with its slick, highly quotable back-and-forth between Billy Crystal and Meg Ryan, as well as its oddly self-reflective quality, felt like something strange and new — the Star Wars of romantic comedies. It wasn’t just a romantic comedy, it was a rom-com. We’ve been living in its wake ever since, and Valentine's Day seemed like a good time to look at the 25 intervening years and pick our favorites.
A couple of caveats: We focused only on American and British rom-coms. In part, this was because there was no way to do justice to all the great films coming out of other non-English-speaking countries. (It wouldn’t have been hard, for example, for us to include 20 French movies on this list.) And also because, let’s face it, a lot of great romantic comedies don’t leave their respective countries’ shores, perhaps because comedy doesn’t always travel as well as action or horror do — resulting in numerous blind spots for us.
Speaking of blind spots: There are movies this list needs. We have a couple of LGBT rom-coms on there, but we wish there could be more. And, while African-American rom-coms, as exemplified in films like The Best Man and Waiting to Exhale (and this week’s About Last Night), have thrived during this time, we couldn’t agree on any titles we felt were strong enough to warrant inclusion on this list.
But without further ado, here are our picks. We await your arguments.