Top Ten Tuesday: The Greatest Romantic Comedies of All Time

Happy Tuesday, dear readers! Each week, we’ll rank the top 10 films in a specific category. While we aim to tie these lists to big releases, that won’t always be the case. Our goal? For you to enjoy, share your own lists, and join in on a lively, friendly debate. This is an interactive space to build community here at The Contending.

No fancy intros, no long essays – just a category and a list. Sound good?

This week, Will Gluck’s One Night Only, starring Monica Barbaro and Callum Turner, arrives in theaters. The premise is exactly the kind of high-concept setup romantic comedies have always thrived on: two strangers collide in a fictionalized New York City on the one night of the year when single people are encouraged to pursue no-strings-attached romance (aka sex). Early reviews suggest the film works thanks largely to the chemistry between Barbaro and Turner, with many affectionately describing it as a sweeter, more romantic take on The Purge.

The “rom-com” has long been one of Hollywood’s most reliable and beloved genres. From the screwball classics of the 1930s to the box office juggernauts of the 1980s and 1990s, audiences could always count on a steady stream of witty, heartfelt stories about people finding love in unexpected ways. While the genre occupies a smaller place in today’s theatrical landscape, its best films remain as charming, insightful, and endlessly rewatchable as ever.

With One Night Only hoping to rekindle some of that magic, it felt like the perfect time to celebrate the genre’s finest achievements.

Here are my ten favorite romantic comedies of all time.