The 42 Best Romantic Comedies of All Time

As this list of the best romantic comedies ever proves, the death of the genre has been greatly—and downright shamefully—exaggerated. Yes, rom-coms have faltered in popularity since their 1990s heyday—but even as time passes, audiences are hungry as ever for banter, meet-cutes, and happy endings. That’s been clear for years now, since Netflix hit pay dirt by releasing scores of rom-coms, Crazy Rich Asians made bank at the box office, and Licorice Pizza became a critical darling. 

This Valentine’s Day offers two heart-on-their-sleeves rom-coms. Genre stalwart Aline Brosch McKenna (Crazy Ex-Girlfriend, 27 Dresses) makes her directorial debut with Netflix’s Your Place or Mine starring Reese Witherspoon and Ashton Kutcher. Meanwhile, real-life couple Alison Brie and Dave Franco team up for Somebody I Used to Know, a 2023 refresh on the mayhem of 1997’s My Best Friend’s Wedding.

Which got us thinking: what are the best romantic comedies of all time, the films that most perfectly exemplify this beloved but under-appreciated genre? Vanity Fair’s Hollywood team decided to find out by making individual top 10 lists, then crunching the numbers and consulting unimpeachable rom-com standards (extra points for a running-through-the-airport or musical serenade scene) for the 42 rom-coms that ultimately made the list. The takeaway, perhaps, is that “romantic comedy” is an elastic designation, one that lies at least partly in the eye of the beholder—appropriate enough for a genre all about falling in love.

Our ultimate list of best romantic comedies is an eclectic mix, containing everything from black-and-white classics to, well, How to Lose a Guy in 10 Days. And while every single pick may not contain every element commonly associated with the romantic comedy, they all fit the American Film Institute’s broad definition of “a genre in which the development of a romance leads to comic situations.” Of course, they’re all funny, too.

FIRE ISLAND, from left: Tomas Matos, Joel Kim Booster, Conrad Ricamora, Matt Rogers, Margaret Cho, Torian Miller, 2022. 

By Jeong Park /Searchlight Pictures /Courtesy Everett Collection.

42. Fire Island (2022)

Jane Austen’s Pride and Prejudice is the narrative basis for this queer romantic comedy, written by and starring Joel Kim Booster. Set in the LGBTQ+ destination of Fire Island, Booster plays Noah, a proudly single nurse whose outlook on dating is rocked by the film’s Mr. Darcy, Will (Conrad Ricamora). Faced with a similar transformation is Howie (Bowen Yang), whose burgeoning courtship with Charlie (James Scully), gets mixed reviews from his friends, including Keegan (Tomás Matos), Luke (Matt Rogers), and Max (Torian Miller). “We made something really, really special and unique and gay,” Booster told Vanity Fair of his celebratory rom-com. “The fact that we did that feels miraculous, considering what we were up against.” Added Yang, “A Jane Austen narrative meeting an Asian American narrative meeting a queer narrative: Those three helices come together in a way that’s greater than the sum of their parts. And to say that something is greater than a Jane Austen narrative is insane—unhinged of me—to do. But I said it.” Even wilder: the movie manages to prove just that. —Savannah Walsh

©Netflix/Courtesy Everett Collection

41. The Half of It (2020)

Netflix has been credited with reviving the rom-com in recent years by distributing popular titles including Set It Up and To All the Boys I’ve Loved Before. But perhaps none has felt as needed as The Half of It—a proudly queer love story from Alice Wu, director of the 2004 cult classic Saving Face. In this Cyrano-inspired tale, high schooler Ellie Chu (Leah Lewis) helps a jock at her school (Daniel Diemer) win the affections of the girl they’re both in love with (Alexxis Lemire). But the film is far less concerned with who will emerge victorious in these efforts as it is the surprising friendship that develops between Ellie and Paul—two people who couldn’t appear more different on the surface. “That’s really just a red herring,” Wu told Vanity Fair of her film’s outcome. “Who gets the girl—not only is it not the important thing in this movie, it’s not the important thing in life. The important thing in life is who you end up connecting with that ends up helping you become the person you need to be.” —Savannah Walsh