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The Greatest Romantic Comedies of All Time, from ‘Some Like It Hot’ to ‘Forgetting Sarah Marshall’

Be it "Bringing Up Baby" or "Breakfast at Tiffany's," from the silent era to the streaming age, these are the best rom-coms ever made.


“Boomerang,” “Bend It Like Beckham,” “Roman Holiday,” “But I’m a Cheerleader,” “Punch-Drunk Love,” “When Harry Met Sally”

Everett Collection

There’s something uniquely cinematic about romantic comedies — something that makes them a natural fit for the movies, and vice-versa. There’s a special alchemy that allows us to believe in the magic of meet-cutes, happily ever afters, and all of the agonizing contrivances that tend to pop up between the two; that gives storytellers permission to transpose the stuff of operas and fables into the fabric of real 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. It’s hard to imagine how the mismatched couple in “Something Wild” might possibly sustain a lasting relationship after the credits roll, but where that movie leaves you — and the journey it takes to get there — is so thrilling and alive that you can’t help but trust it. Literally nothing in “Love Actually” makes sense if you stop and think about it for even a few seconds, but love, actually, always seems to add up in the moment.

Richard Curtis’ magnum opus was a British production (in case you couldn’t tell), but even some of its many storylines find something naggingly American about the aspirational nature of the rom-com genre. 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 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 doesn’t see the same value in the genre that it once did.

Of course, the romantic comedy is also something of a universal language, and other film industries (Bollywood most of all) have been churning these stories out for local audiences faster than we can hope to keep up. Fingers crossed that we find a way to disentangle “foreign cinema” from the arthouse, because there are so many mainstream hits from around the world that never make it to American screens.

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.

Anne Thompson, Chris O’Falt, Zack Sharf, Jude Dry, Ryan Lattanzio, Tambay Obenson, Tom Brueggemann, and Samantha Bergeson also contributed to this list. 

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