The 20 Greatest Romantic Comedies of All Time

Every Valentine's Day, the "I hate rom-coms" crowd comes out, decrying the subgenre as either a homogenous mass of the same tired tropes or as an elaborate fantasy with no bearing on "real" relationships. While it's certainly possible to dislike most rom-coms, we'd argue that almost everyone can find at least one romantic comedy that resonates with them. What's often missing from these arguments, as longtime fans of the subgenre will tell you, is that rom-coms actually represent a wide range of films, from the biting to the effervescent, and if you don't like them it usually just means you haven't met your match yet. So, we're here to help. Just in time for Valentine's Day, here are 20 of the greatest romantic comedies ever made (presented in chronological order), including plenty of offerings for the "I hate rom-coms" team.

1. It Happened One Night (1934)

Frank Capra's legacy as one of the great benchmark filmmakers also includes a benchmark romantic comedy that, nearly a century after its premiere, is still one of the best examples of an odd couple love story. What's most striking about It Happened One Night today, other than the undeniable chemistry of its stars, is just how stripped down much of it is compared to the glamour and spectacle of its rom-com descendants. Claudette Colbert and Clark Gable are asked to carry much of the movie in intimate, rather bare settings. But whether they're dividing up a tiny bedroom or hitching a ride on the side of the road, they make the entire journey worth it—even to modern eyes.

2. Ninotchka (1939)

The famously distant Greta Garbo might not seem like the best casting choice for a romantic comedy to modern audiences, but in Ninotchka, director Ernst Lubitsch found the perfect vehicle for her gift of pivoting on a dime between icy and joyous. This story of an all-business Russian negotiator (Garbo) and the nobleman (Melvyn Douglas, in top form) who teaches her to have fun in the Western world remains one of the best examples of odd couple romance in the history of the subgenre. While its satire of pre-World War II Communism might not have aged very well, the scenes of Garbo and Douglas getting drunk together remain utterly delightful.

3. The Philadelphia Story (1940)

One of the great George Cukor's contributions to the rom-com canon (Adam's Rib is another notable entry), The Philadelphia Story is both a beautifully engineered film and a display of the raw acting power of Katharine Hepburn. In a film in which she's asked to play a socialite ultimately choosing between Cary Grant and Jimmy Stewart, she somehow manages to outshine both of them, often in the course of the same scene, even as Grant and Stewart are also doing some of their very best comedic work in the film. Stewart drunkenly carrying Hepburn while singing at the top of his lungs remains one of the great romantic comedy moments.

4. His Girl Friday (1940)

His Girl Friday is one of the best workplace romances ever made and one of the best reconciliation romances ever made thanks to the near-incomparable chemistry of Cary Grant and Rosalind Russell. Howard Hawks's legendary film is perhaps best remembered today for its lightning-fast, "realistic" dialogue that used the then-revolutionary tactic of having characters talk over each other. But what makes it an enduring romantic comedy is just how much Grant and Russell crackle from their very first scene together. They're both so undeniably game for the wackiness of the script and the way their characters seem to intellectually spar at every turn, and it makes all the difference.

5. Roman Holiday (1953)

Perhaps the ultimate fairy tale romantic comedy (even considering the ones that are actual fairy tales), Roman Holiday is the purest expression of the destination rom-com, combining undeniable star power with beautiful locations and the simple magic of William Wyler's direction. Audrey Hepburn is effervescent in the role of a princess looking for an ordinary day in Rome, while Gregory Peck works his gravitas and charm like a master, drenching the entire movie in that sense of possibility and wonder that we all long for when we travel.

6. Desk Set (1957)

The legendary on-and-offscreen pairing of Katharine Hepburn and Spencer Tracy may have reached its zenith with Guess Who's Coming to Dinner, but if you want to see the duo in peak romantic comedy form (sorry, Adam's Rib), look no further than this wonderfully enemies-to-lovers romance. Directed by Walter Lang and written by Phoebe and Henry Ephron (parents of future rom-com luminaries Nora and Delia Ephron), Desk Set is the story of a preternaturally intelligent research librarian (Hepburn) and the efficiency expert (Tracy) who comes into her office looking to replace her with a supercomputer. Instead, he finds her irreplaceable in more ways than one. The scene in which Tracy's character grills Hepburn amid a freezing rooftop lunch is pure mismatched rom-com gold.

7. The Apartment (1960)

Billy Wilder might be the patron saint of the modern romantic comedy film, thanks to all of his work in the subgenre over the years. While Some Like It Hot is usually the entry in his filmography that gets the most love, The Apartment remains his masterpiece. It's less zany and considerably darker than Some Like It Hot, to be sure, but Jack Lemmon and Shirley MacLaine rise to the challenge of imbuing Wilder and I.A.L. Diamond's more subdued script with vibrant, bittersweet comedy. It's a film packed with details that feel supremely honest about how love works sometimes, and Lemmon straining spaghetti with a tennis racket is still one of the all-time great rom-com moments.

8. Some Kind of Wonderful (1987)

John Hughes is perhaps the most famous practitioner of the teen comedy ever. And when it comes to his rom-coms, it's easy to single out Pretty In Pink or Sixteen Candles as the bright spot. Look closer, though, and you'll find one of his final teen movie efforts is actually his most sophisticated. Some Kind of Wonderful, which re-teams Hughes and Pretty In Pink director Howard Deutch, actually reads in some ways like a re-take on the class-divide dynamics of their earlier collaboration, but with some notable upgrades. It's deeper than Hughes's previous teen romantic comedy takes, in that it's less like a fairy tale and more like a real high school romance, and the trio of Eric Stoltz, Lea Thompson, and Mary Stuart Masterson is still one of cinema's great unsung love triangles.

9. Moonstruck (1987)

Norman Jewison and John Patrick Shanley's Moonstruck is a film so embedded in pop culture that it's delivered not one but two moments iconic even to viewers who've never actually seen the film. More than three decades after its release, "Snap out of it!" remains one of the most memorable romantic comedy lines ever, and Cher's dazzling display of morning-after bliss as she kicks a can through the streets of New York City remains an indelible symbol of what it's like to fall for someone completely. Plus, though Cher and Nicolas Cage are the clear stars, Olympia Dukakis—who won the 1988 Oscar for Best Supporting Actress, while Cher took the Academy Award for Lead Actress—is still able to steal the movie right out from under them as a woman who knows that real, lasting love often carries a bittersweet edge.

10. When Harry Met Sally… (1989)

No list of the greatest romantic comedies ever made is complete without Rob Reiner's classic tale of two friends who spend more than a decade trying to figure out if they're really just friends, or something more. Written by the legendary Nora Ephron and brought to captivating life by a cast led by Billy Crystal, Meg Ryan, and Carrie Fisher, Reiner's film now plays like a checklist of everything audiences could ever want from a romantic comedy made in the last 35 years—from philosophical discussions about the nature of relationships to the cathartic confession of love in the final act. There's a reason that nearly every rom-com made since has been measured against this one.

11. Defending Your Life (1991)

Leave it to Albert Brooks to craft the perfect encapsulation of love overcoming fear via an extended fantasy saga about the bureaucracy of the afterlife. Brooks's comedies are so often focused on skewering the hyper-commercial, status-obsessed culture in which they were made, and that's still present here. But what holds up best about Defending Your Life 30 years later is just how well it works as a sheer expression of the transformative power of love. By the end, all traces of cynicism and fear have faded, and in their place is an honest expression of joy. Brooks's casting of Meryl Streep as his love interest didn't hurt, either.

12. Boomerang (1992)

Eddie Murphy's first attempt at pure romantic comedy is, despite a few jokes that haven't aged well, one of his best efforts as a leading man. Reginald Hudlin's Boomerang packs a cast of all stars—including Murphy, Halle Berry, and a scene-stealing Grace Jones—and a script full of memorable lines into this story of a man who's thrown for a loop when he finds a woman (Robin Givens) who's actually better at playing his own suave one-night stand game than he is. Berry and Givens are both wonderful foils to Murphy, Jones is predictably magnificent, Eartha Kitt turns in some scene-stealing of her own, and Murphy himself delivers some of the best pure comedy of his career with one instantly memorable sex scene. Boomerang is an ahead-of-its-time classic.

13. Four Weddings and a Funeral (1994)

Richard Curtis has had a hand in several of the most beloved romantic comedies of the last 30 years, from Notting Hill to Love Actually, but one of his earliest efforts remains his best. This Curtis-scripted, Mike Newell-directed classic about a group of friends navigating the ups and downs of life while one of them finally figures out what he really wants remains an utterly charming staple that cemented Hugh Grant's position as everyone's favorite charmingly befuddled British boyfriend.

14. Clueless (1995)

For a great many movie fans who came of age in the 1990s, Amy Heckerling's Clueless is still the standard by which all other rom-coms are measured. An adaptation of Jane Austen's Emma that somehow never feels dated despite its frequent reliance on very '90s slang and very '90s fashion, the film is packed with unforgettable dialogue, costume design, and soundtrack choices. What makes it such a persistent classic, though, is the heart beating at its core as a story of a young woman (Alicia Silverstone) who seems to have thought of everything except the one thing she actually wants most.

15. You've Got Mail (1998)

Nora Ephron is the doyenne of the modern romantic comedy thanks to more than one film, but if you have to pick a single entry from her work as a writer and director, You've Got Mail is the one that still packs the most resonance for 21st century audiences. Like her 1993 triumph Sleepless In Seattle, it deals with the feeling of being lost and adrift even when surrounded by a city full of people, but it also goes further to explore ideas of connection in a world where distance and even physical connection aren't necessarily barriers to romantic attraction. Which is even more impressive when you consider that it was inspired by Parfumerie, a 1937 Hungarian play that Ernst Lubitsch had adapted into The Shop Around the Corner in 1940. Tom Hanks and Meg Ryan are reliably wonderful in the film, particularly when they have to sell the idea that these two characters could fall in love despite the various online manipulations that lead them to romance. In the hands of other actors, it might be suspect. With these two, it feels meant to be.

16. But I'm a Cheerleader (1999)

No other film on this list, and indeed no other film ever made, looks and feels quite like But I'm a Cheerleader, Jamie Babbit's cult classic ode to living your truth and finding love on your own terms. Natasha Lyonne and Clea DuVall shine—amid scene-stealing turns from Cathy Moriarty, Melanie Lynskey, and RuPaul—as two young women who fall for each other while they're supposed to be getting "cured" at a gay conversion therapy camp, and the emotional weight of their performances is even more striking when you consider the overall production design around them. But I'm a Cheerleader takes place in a world where every color is bright and everything is coordinated, suggesting a world of absolutes that the characters must navigate to discover that who they really are is not so easily defined.

17. The 40-Year-Old Virgin (2005)

The 2000s brought with them a new wave of hard-R comedies centered on immature men just trying to grow up, but Judd Apatow's directorial debut remains the best of them in terms of romantic comedy force. What from afar sounds like a bad joke, or at least a one-note premise, quickly pivots into something heartfelt in actual practice, as Apatow and his all-star cast craft a story of a man (the incredible Steve Carell) working to overcome his romantic fears not through slick pick-up lines and body waxing (though he tries both) but through sheer force of warmth and kindness. And as great as Carell is, casting Catherine Keener as the romantic interest is the stroke of genius that pushes it through to classic status.

18. It's Complicated (2009)

As Nora Ephron's film career slowed in the 21st century, Nancy Meyers emerged as the clearest heir to her brand of beautifully orchestrated, bubbly rom-coms that nevertheless pack a serious emotional punch. In Meyers's filmography, though Something's Gotta Give and The Holiday certainly hold a special place in the rom-com canon, It's Complicated reigns as the most sophisticated representation of her style, particularly her attempts to chronicle the ups and downs of being middle-aged and in love. Meryl Streep is, of course, fantastic, and Steve Martin proves he's welcome at the rom-com table anytime in a film that also includes wonderful, warm performances from Alec Baldwin, John Krasinski, Zoe Kazan, and more.

19. The Big Sick (2017)

Based on the real-life love story of writers Kumail Nanjiani (who also stars) and Emily V. Gordon, The Big Sick is a romantic comedy about what happens when life, and the looming possibility of death, gets in the way to such an extent that your love story is sometimes more about holding on than it is about holding each other. Director Michael Showalter's absurdist tendencies (this is one of the minds behind Wet Hot American Summer) are softened a bit by the heart of the film, but they're still just present enough to play up how strange this journey is for the people at the core of it, and that makes the emotional payoff all the more intense.

20. Palm Springs (2020)

The perfect romantic comedy for 2020 is also one of the best films in the subgenre about learning to be comfortable with someone even as the world around you bleeds into same-ness at an alarming rate. Andy Samberg and Cristin Milioti are a perfect rom-com pair, playing to each other's strengths in a way that makes it feel like they've been at it for years. And the time loop concept at the core of the story works wonderfully as both a metaphor for navigating long-term relationships and a clever premise to show what happens when you care enough to break through to the next stage of the commitment. This film is destined to be a lasting part of the rom-com canon.