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50 Greatest Romantic Comedies of All Time

From ’30s screwballs to 21st-century meet-cutes, Rock and Doris to Hanks and Ryan — our picks for the best rom-coms ever

Say Anything, Moonstruck, When Harry Met Sally

Moviestore Collection/Shutterstock (2);Castle Rock/Nelson/Columbia/Kobal/Shutterstock

Take two people. Find a way to pair them up — maybe they’re on a cross-country trip together, maybe they both work in the same office, maybe they’re rivals in the same industry. Better yet, they might even be two parts of a love triangle. The scenarios are endless. Now throw some obstacles in their way, from geography to class issues to vengeful exs and/or brand new beaus. Or the conflict could be as easy as the fact that they just don’t like each other — in fact, they despise the other person. Then, after a lot of comic shenanigans and trying circumstances, they realize that they’re really meant for each other. Cupid’s arrows hit their marks. Roll credits.

It sounds simple, right? But to make a great romantic comedy — like, a really classic, stand-the-test-of-time one — requires skill, chops, expert timing, the right chemistry among your leads and the ability to pull heartstrings and hit funny bones at the same time. It’s a tougher balancing act than most folks would care to admit, and all the more impressive when filmmakers and actors actually do pull it off.

And the romantic comedies we’ve singled out here aren’t just impressive — they are, in our humble opinions, the cream of the genre crop, the best of the best. In honor of Valentine’s Day, a.k.a. the holiday where everyone craves both rom-com viewing time and argument-starting ranked lists, we present our choices for the 50 best rom-coms of all time. From ’30s screwballs to 21st century meet-cutes, Rock and Doris to Tom and Meg, these are the ones that had us at “hello.”