The Best Rom-Coms of All Time, from ‘Some Like It Hot’ to ‘Roxanne’

The Best Rom-Coms of All Time, from ‘Some Like It Hot’ to ‘Roxanne’

There’s something uniquely cinematic about romantic comedies — something that makes them a natural fit for the movies and vice-versa. There’s an intoxicating alchemy that allows us to believe in the magic of meet-cutes, happily-ever-afters, and all the agonizing contrivances that tend to pop up between the two. Love it seems gives storytellers permission to transpose the stuff of operas and fables into the fabric of real (or at least overly glossed but still recognizable) life.

On paper, a film like “Pretty Woman” might be a retrograde fairy tale about a sex worker with a heart of gold and the rich businessman who can afford it, but the chemistry between Julia Roberts and Richard Gere is so explosive that you surrender to the sentiment of it all. Literally nothing in Richard Curtis’ “Love Actually” makes sense if you stop and think about it for even a few seconds. The same could be said of Robert Iscove’s “She’s All That,” or Blake Edwards’ “Breakfast at Tiffany’s.” And yet, love always seems to add up in that magical movie moment.

Richard Curtis’ holiday-themed magnum opus was a British production (in case you couldn’t tell), but many of its storylines find something naggingly American about the aspirational nature of the rom-com genre. The genre seems to (incorrectly) suggest no other country is populated by such radically different strangers, nor so enriched by the unexpected collisions between them; from “Bringing Up Baby” to “Forgetting Sarah Marshall,” Hollywood has always been eager to sell the idea that, in the United States, we’re all just one chance encounter away from happiness.

That might help to explain — if only in part — why the rom-com canon is as white and heteronormative as the history of the American film business, and why that canon is ripe for re-evaluation now that Hollywood is reassessing the marketability of diverse love stories in the streaming age. In 2022, Nicholas Stoller’s “Bros” starring Billy Eichner and Luke Macfarlane made history as the first gay rom-com produced and distributed by a major movie studio. What’s more, the romantic comedy is a universal language. Other film industries — Bollywood most of all — have been churning these stories out for local audiences faster than Americans can hope to keep up.

In that light, IndieWire’s list of the Best Romantic Comedies of All Time is more of a start than a final statement; it’s a living document that we’ll change up and add to as time goes by. One thing that will stay the same, however, is that rom-coms have a recognizable grammar all their own; meet-cutes, montages, banter, a weird preponderance of journalists, sex scenes that always indicate a dark turn at the end of the second act. These aren’t just love stories that happen to be funny, they’re a sacred art unto themselves. And these are the masterpieces that prove it. Here are the 84 best romantic comedies ever made.

Wilson Chapman, Anne Thompson, Chris O’Falt, Zack Sharf, Jude Dry, Ryan Lattanzio, Tambay Obenson, Tom Brueggemann, David Ehrlich, Eric Kohn, Kate Erbland, and Samantha Bergeson also contributed to this list. (Editor’s note: The following was originally published in February 2020. It has been updated multiple times since.)