top 40 rom-com movies you should watch
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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.
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
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
40. My Big Fat Greek Wedding (2002)
The joy of My Big Fat Greek Wedding, starring and written by Nia Vardalos, is that it’s actually several films baked into one. Romance! Comedy! Culture shock! The secret healing powers of Windex! Vardalos’s ode to Greek culture in all its beauty and frustration focuses on the quest of her character, Toula, to get her family to accept her non-Greek partner, Ian (played by John Corbett). It’s the definition of a romp, with kooky characters and their absurdist takes on life spilling out of every scene. Each character is given so much personality and so much attention that My Big Fat Greek Wedding could be splintered into several offshoots following the antics of Aunt Voula (a rib-achingly funny Andrea Martin) or the headstrong Gus (Michael Constantine), who can trace anything and everything back to Greece. But it’s the romance, which Vardalos pens so sweetly, that grounds it all. We trace Toula and Ian’s relationship from the very first time they lay eyes on each other, all the way to Ian’s intimate proposal. A film this big and sweeping needs an anchor, and these two do quite nicely. —Yohana Desta
39. Something’s Gotta Give (2003)
Here’s a little ditty about Jack (Nicholson) and Diane (Keaton), the silver-haired leads of Nancy Meyers’s best romantic comedy. Though some industry insiders may have been wary of a film about people in their 50s and 60s falling in love, audiences were ready for a mature romance—one that involved a hilarious sex scene in which Keaton’s character takes Nicholson’s blood pressure to make sure he doesn’t have a heart attack during the act. The film grossed over $266 million worldwide and nabbed Keaton an Oscar nomination. It also gave us a heartsick Nicholson, a lady killer on-screen and off, crying over a girl for a change. —Anna Lisa Raya
38. Kissing Jessica Stein (2002)
Romantic comedies have traditionally been tough territory for queer characters, who tend to fall into simplistic, stereotypical best-friend roles when they’re allowed to join the party at all. (We can never forgive the Sex and the City movies for what they did to Stanford and Anthony.) Enter Kissing Jessica Stein, which even 16 years later remains one of the few mainstream, widely distributed romantic comedies to focus on same-sex attraction—and between queer women, no less, who are even tougher to find in these sorts of movies than queer men. Even discounting its milestone elements, the film does an admirable job of balancing rom-com clichés (the overbearing Jewish mother! The heroine with a job in New York media!) with more offbeat flourishes, making it an Annie Hall descendent tailor-made for a new millennium. —Hillary Busis
37. Defending Your Life (1991)
If nothing else, the rom-com genre has given us the scene in which an ever-anxious Albert Brooks watches a near-angelic Meryl Streep slurp down a never-ending noodle. The pair’s chemistry as Daniel and Julia is on full display in Defending Your Life, a witty exploration of the afterlife written and directed by Brooks. In the film, the pair’s post-death fates are decided in Judgment City, where their actions (or inactions) on Earth are litigated. Unsurprisingly, meeting the love of your life in the place where you’re forced to defend your own is a bit of a drag. If Daniel can’t properly justify his way of living, he’ll be forced to do it all over again, leaving Julia behind. And if you thought running through the airport was a wildly romantic gesture, try chasing after a tram headed to the next plane of human existence. —Savannah Walsh
36. How to Lose a Guy in 10 Days (2003)
Only in the rom-com to end all rom-coms would you have leads named Andie Anderson and Benjamin Barry. From the jump, How to Lose a Guy in 10 Days is precisely as frothy as it sounds—a film that centers on a Cool Girl, before the term came into vogue, whose chemistry with a mildly chauvinistic man’s man is undeniable even though their romance is doomed from the start. She’s a writer at a women’s magazine trying to carve out a space where she can write about subjects of substance—which, for the moment, requires her to ensnare a man and torture him to the point of breaking up. He, meanwhile, is simply trying to prove he can make any woman fall in love with him. Kate Hudson and Matthew McConaughey sold their characters with wit and panache—throwing themselves into the roles completely, but delivering certain lines with just a whiff of irony. By the end, Andie has dragged “Benny Boo-Boo . . . Boo-Boo-Boo” to a Céline Dion concert, and he’s dragged—I mean, brought—her to Staten Island to meet his family after just a few days of dating. Yet as they kiss and make up on the bridge after a truly humiliating karaoke-fight in front of everyone they know, it’s basically impossible to do anything but cheer. —Laura Bradley
35. Never Been Kissed (1999)
In 2011, Adele revealed that the soaring bridge of her song “One and Only” was inspired by this Drew Barrymore classic. “You know at the end, when she describes being kissed as the whole world slows down and goes in slow motion, everything else goes blurry…I kind of see it like that,” the Grammy winner explained. “Whenever I hear the bridge…it’s quite epic. I mean, I don’t think Never Been Kissed is a particularly epic movie…” Apologies to Adele, but on this point we’ll politely disagree. Barrymore plays Josie Geller, a junior copywriter at the Chicago Sun-Times who poses as a student at her former high school for an ill-conceived undercover piece. In between trying pot brownies and getting a sex-ed lesson from her co-worker (played by the scene-stealing Molly Shannon), Josie (hold the Grossie) falls for her dreamboat English teacher, Sam Coulson (Michael Vartan). Although the specifics surrounding that romance are slightly problematic, the slapstick sweetness of the movie’s premise endures. So much so that Barrymore often reprises the role for segments on her similarly spirited daytime talk show. —Savannah Walsh
34. Some Kind of Wonderful (1987)
Of all the kids from the wrong side of the tracks in the John Hughes universe, perhaps none were as cool as Eric Stoltz’s Keith (an artsy outcast), Mary Stuart Masterson’s Watts (his tomboyish best friend), and Lea Thompson’s Amanda Jones (beautiful and popular, but poor). Their high-school love triangle came with a surprise ending, one in which Amanda dumps her jerk boyfriend—and Keith’s amazing attempts to woo her with the best date ever—to “learn to stand on my own.” She goes solo while Watts lands the boy—a heretofore oblivious Stolz—who ends the film with one of the best lines in the canon: “You look good wearing my future.” The film also boasts one of the better soundtracks to come out of the 80s, and is what we have to thank for current-day rom-com heroine, Zoey Deutch: her parents are Thompson and the pic’s director, Howard Deutch, who met on the film. —Anna Lisa Raya
33. Crazy Rich Asians (2018)
When Crazy Rich Asians opened to blockbuster numbers in the summer of 2018, the world was ready for a different kind of romantic comedy. It had been decades since 1993’s The Joy Luck Club—the last major American studio release to feature a predominantly Asian and Asian-American cast—and the rom-com genre was experiencing a dry spell. Then along came Jon M. Chu’s sparkling adaptation of Kevin Kwan’s bestselling novel, centered on the love story between Rachel (Constance Wu) and Nick (Henry Golding)—and how their romance is tested by the latter’s exorbitantly wealthy, slightly unhinged family. Every frame bursts with opulence, from Michelle Yeoh’s steely performance as Nick’s elegant mother Eleanor or one of the most lavish wedding scenes ever committed to film. Sequels are reportedly in the works—and they couldn’t come soon enough. —Savannah Walsh
32. Annie Hall (1977)
What to do about Annie Hall, an indisputable rom-com masterpiece whose reputation has arguably been overshadowed by the troubling allegations lobbed against its writer, director, and star nearly two decades after its 1977 release? Particularly in this case, there’s no way to separate the art from the artist; Annie Hall is Woody Allen through and through, from its narration—equal parts heady philosophy and Catskills-inflected humor—to its female characters, who fall rather neatly into two distinct buckets: dream girls and nightmares. (On separate occasions, Diane Keaton, delivering her signature performance, gets to be both.) Even so, the film has a certain magic to it—a wistful sweetness underpinning its remarkably quotable jokes, rounding out what could have been an episodic collection of (very good) punch lines. A nostalgic yearning for a simpler time and place, when falling in love was within reach, and you didn’t know quite as much as you know now. —Hillary Busis
31. Much Ado About Nothing (1993)
Kenneth Branagh! Emma Thompson! Denzel Washington! Keanu Reeves! Michael Keaton! Kate Beckinsale! Robert Sean Leonard! The cast alone is worth much ado—and in execution, too, this production (also directed and scripted by Branagh) sings. In the ever-sparring Beatrice and Benedick, whose sexual tension is only heightened by their equally sharp tongues, Shakespeare created an archetypal couple whose bantering dynamic would inspire countless imitators and descendants—and Thompson and Branagh embody the lovers beautifully, imbuing centuries-old characters with modern wit and charm. A more recent adaptation—the 2012 version directed by Joss Whedon—is also worth a look for rom-com historians. —Hillary Busis
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