The 25 Best Romantic Comedies of All Time

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The death of the romantic comedy has been greatly exaggerated. Yes, the genre has faltered in popularity since its 1990s heyday—but recent developments prove that audiences are still hungry as ever for banter, meet-cutes, and happy endings. This summer, Netflix has hit pay dirt by leaning hard on frothy comedies about pretty young things falling in love; this week, Crazy Rich Asians will storm theaters, putting a new sort of gloss on a tale as old as time.

Which got us thinking: what are the films that best exemplify this beloved but under-appreciated genre? After each member of Vanity Fair’s Hollywood team, including all three of our critics, came up with his or her own personal top 10 list, we crunched the numbers, noting which films appeared most frequently, and—after a few brief arguments about what constitutes a romantic comedy, and what does not—came up with the final tally. Though 25 movies ultimately made the list, 20 more were left off because they received only a single vote—films that ran the gamut from Obvious Child to White Christmas to Strictly Ballroom to Wall-E. 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 focused on love.

Our ultimate list 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.

25. 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

24. 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 finding 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

23. 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

22. 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

21. 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

20. Annie Hall (1977)

What to do about Annie Hall, an indisputable 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 love was within reach, and you didn’t know quite as much as you know now. —Hillary Busis

19. 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

18. Amélie (2001)

It’s not a movie that many would traditionally classify as a romantic comedy, but Amélie defies most easy classification (unless you consider “French whimsy” a genre unto itself). The sweet 2001 film, directed by Jean-Pierre Jeunet, is about a painfully shy Parisian waitress who finds joy and peace in the little things, like skipping stones, cracking fresh crème brûlée, and looking out over the city and wondering: “How many couples are having an orgasm now?” Audrey Tautou brings every ounce of heart to the role, playing Amélie as a wide-eyed gamine who finds her first rush of confidence when she helps a blind man across the street (a most memorable scene bursting with life). Romance is never her direct goal, but it’s a gentle throughline—that is, until love at first sight whacks her in the face at a train-station photo booth when she lays eyes on a man named Nino. Amélie’s true-love discovery doesn’t take any easy, obvious routes, but it does, finally, culminate in a heart-stopping little poem of a scene. Kissing someone on the eyelids never looked so romantic. —Yohana Desta

17. The Apartment (1960)

Is The Apartment even really a romantic comedy? Re-watching it recently, I was struck by how tragic it is: a comedy that goes out of its way to remind you of the pitfalls of falling in love, especially with married men, or someone who’s in love with a married man. It’s also a comedy in which the ostensible “nice guy” lets himself be drenched in the muck of all the bad men working above him, a hardly willing enabler of their secret sex lives. I guess the term we use nowadays for a guy like C.C. Baxter (Jack Lemmon) is “cuck,” and it’s true that one of the genius moves Billy Wilder makes in this movie is to make it seem so unlikely, from the start, that a pushover nebbish like Baxter and the heartbroken, helplessly charismatic Fran Kubelik (Shirley MacLaine), an elevator girl in Baxter’s building, will even wind up together. We’re not even sure it’s a question worth asking—it’s beautifully implausible. One of the brilliant things about The Apartment—especially now, with our new sensitivity to workplace harassment and the bad behavior of men in power—is that even from the vantage of 1960, the movie knew just how transactional sex and romance could be, sometimes willingly and often not. It’s one of the great workplace comedies—a movie worth watching again with fresh eyes. —K. Austin Collins

16. Four Weddings and a Funeral (1994)

Who doesn’t love a movie that opens with characters shouting “fuck fuck fuck” as they scramble wildly to make it to a friend’s wedding? Everything about Richard Curtis’s Four Weddings and a Funeral seemed determined to unravel the traditional rom-com, even as it wore its sentimentality on its sleeve. Instead of one marriage, there are a whole slew of them. A fairly central character is killed off (precipitating the funeral of the title). And the movie’s object of desire, an American woman played by Andie MacDowell, actually marries another man at one point. The ensemble cast is charmingly quirky (particularly the late Charlotte Coleman), but Four Weddings is best known for launching Hugh Grant on his long career as an awkward, floppy-haired, stuttering romantic hero who somehow overcomes his deeply British reserve to confess his true feelings. It’s a messy romp that opened up territory for decades of rom-coms to come. —Joy Press

15. Moonstruck (1987)

Nearly two decades before John Patrick Shanley earned the Pulitzer Prize and Tony for penning Doubt, the revered writer won an Academy Award for Moonstruck—one of the few romantic comedies so superb that even Hollywood’s genre-snob voters fell victim to its charm. (In addition to Shanley’s win, Cher and Olympia Dukakis also won Oscars for their roles as mother and daughter.) Directed by Norman Jewison, Moonstruck features Cher as an Italian-American widow living with her parents in Brooklyn, when she falls for her fiancé’s younger brother, played by Nicolas Cage. Though Cher has said that she has a narrow range as an actress, and claimed that she only plays variations of her real-life persona, her performance as Loretta Castorini attests that her “narrow range” is anything but. —Julie Miller

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

Though his previous contributions to pop culture went criminally under-appreciated—it would take years for Freaks and Geeks and Undeclared to get their deserved due—Judd Apatow’s 2005 feature directorial debut, The 40-Year-Old Virgin, was a career turning point. The uproarious comedy—co-written by Apatow and star Steve Carell, though also heavily improvised—proved Apatow’s unique ability to interweave original, laugh-out-loud humor with surprising sweetness. In addition to cementing Carell as a Hollywood star, the ensemble blazed a new comedy sub-genre (men-children—and later, via HBO’s Girls, women-children—clumsily coming to terms with adulthood) and launched Apatow as something of a Hollywood tastemaker, whose mere association with a project signaled that it would be funnier than most, and full of performers who should be on audience’s radars. —Julie Miller

13. Down with Love (2003)

Peyton Reed’s sleeper classic, starring Renée Zellweger and Ewan McGregor, wasn’t especially well-received when it was released in 2003, which I have a theory about. The movie is an unabashed confection: candy-coated to the point of causing cavities, and excessively rich with wink-winking nods to the Doris Day movies that inspired it. Down with Love was definitely a tough sell in the midst of a brewing Iraq War; it couldn’t have seemed more frivolous. But all that sugar was just a cover for what’s really at stake here, which is a re-writing of movie romances and their ongoing battles of the sexes. The film, about a star writer’s proto-feminist attempt to get women to live and love on their own terms and the magazine writer trying to bring her down, doesn’t have an outwardly cynical bone in its body. But its characters do: these are people who know the strategic ins and outs of romance, and spend an entire movie one-upping each other. It all builds toward one of the finest moments of Zellweger’s acting career (which is saying a lot): a heart-stopping monologue about the things a woman might do just to get noticed by the man she loves. At the center of all this silliness is a character who truly deserves a happy ending—but not at the expense of the newfound freedom she inspired in everyone else. —K. Austin Collins

12. His Girl Friday (1940)

Cary Grant and Rosalind Russell teamed up for this fast-talking newspaper screwball comedy from director Howard Hawks. The film is older than most of the other rom-coms on our list, but in many ways, it was before its time—a media-world romance fueled by talky, mile-a-minute romance banter that posited the chemistry between Grant and Russell as a meeting of equally sharp minds with the same nose for news. In adapting the 1928 play The Front Page, Hawks altered the workplace dynamics of workaholic crack reporters in Chicago with one fell swoop: he turned Hildy Johnson into a snappy, bold female reporter—and the ex-wife of Grant’s Walter Burns, the sly, knowing editor of The Morning Post with a booming voice and irresistible charm. His Girl Friday lays on the paternalism of the 40s pretty thick—Walter sabotages Hildy’s relationship with another man, and delights in cornering her into doing more work—but her final decision, between the monotony of domesticity and the thrill of chasing the next story, rings true nearly 80 years later. — Sonia Saraiya

11. My Best Friend’s Wedding (1997)

Julia Roberts rebounded from a little career slump (if you love trouble and want something to talk about, watch Mary Reilly) with this utterly effervescent anti-romance, a prickly and witty comedy of jealousy that finally let Roberts show the hard edge lurking behind her thousand-watt smile. (We’d argue she never again played a true innocent after My Best Friend’s Wedding.) In P.J. Hogan’s film, Dermot Mulroney is the perfect soft surface for Roberts to throw darts at, while Cameron Diaz is hateable and relatable in a committed performance that solidified her star. But it’s Rupert Everett, playing one of the early rom-com gay besties, who nearly saunters off with the movie. When he and Roberts are a’banter, My Best Friend’s Wedding makes its most salient observation: sometimes it’s friendship, not romance, that rescues us—and redeems us, too. —Richard Lawson

10. Sleepless in Seattle (1993)

Come for Nora Ephron’s first hit as a director with this unlikely 1993 romantic comedy, which begins with Tom Hanks mourning the loss of his beloved wife and mother. Eventually, he finds a second chance at love via a radio show, an homage to An Affair to Remember, and a manipulative 8-year-old, played with aplomb by Ross Malinger. Stay for a young Gaby Hoffmann and her precocious pre-iChat lingo, and Annie’s (Meg Ryan) journalistic tenacity, which allows her to track down Mr. Sleepless in Seattle even in a pre-Google, pre-LexisNexis environment. The movie verges into stalker territory with Annie’s willingness to cross the country in search of her true love, but Hanks is pitch-perfect as the bereaved husband and doting father. (The scene with him describing to Jonah how his mom could peel an apple in one long slice while “Bye Bye Blackbird” plays in the background is still a stunner.) And questionable elements or not, you’ll still wind up rooting for the duo’s long-awaited meet-cute atop the Empire State Building. —Nicole Sperling

9. Broadcast News (1987)

James L. Brooks wrote, produced, and directed this seven-time Oscar nominee, which put a slight little Southerner named Holly Hunter on the map and predicted the slow decline of American journalism. But above all, Broadcast News is a love story—between three career-minded journalists and the industry they adore, which tangles them into an achingly empathetic love triangle that puts each character on a path to heartbreak. Hunter’s character, a TV news producer, is as smart and honorable as her best friend, a journalist played by Albert Brooks. But she’s taken by the new anchor, played by William Hurt, and ends up in a quandary that tests her heart, in a competitive environment with very little room for softer emotions. Every performance in this film is a gem, and James L. Brooks guides the viewer so expertly that its paces feel inevitable, even as they jerk tears. Unlike most rom-coms on this list, Broadcast News doesn’t end with a happily paired off couple. But it does feature Hunter in a fabulous polka-dotted dress on her way to the White House Correspondents’ Dinner, which is just as good. —Sonia Saraiya

8. It Happened One Night (1934)

A rom-com made in an era when the production code discouraged scenes of “excessive passion,” It Happened One Night captures love and even lust without a whole lot: an expertly displayed leg, an instantly iconic shirtless Clark Gable, and a road-trip plot repeated endlessly in the decades since but never quite matched. A model of the screwball-comedy era, when dialogue came quickly and women behaved wildly—but lovably—It Happened One Night holds up particularly well thanks to the chemistry between Gable and Claudette Colbert, who plays the heiress on the run being hunted down by Gable’s enterprising reporter. Their relationship is sparring and hilarious, the two clearly perfectly matched in wits, until it turns irrepressibly romantic, with Colbert’s Ellie running away from her unwanted wedding to “pill of the century” Westley (Jameson Thomas) to be with her hunky newspaperman. The Walls of Jericho tumbled, five Oscars were won, and the cinematic template was set for pairs who just can’t stop arguing, so they may as well kiss already. —Katey Rich

7. Notting Hill (1999)

She was just a girl standing in front of a boy, asking him to love her—except she was Julia Roberts, fresh off the success of My Best Friend’s Wedding, and he was Hugh Grant, post–Sense and Sensibility. In other words, these were two beloved actors stretching some already toned muscles, and it showed. Notting Hill unfolds like a modern-day fairy tale, as a wildly famous actress falls in love with a humble shopkeeper. The clothes might be dated—1999 was a truly embarrassing year for all of us—but the appeal is eternal. It checks all the boxes: the meet-cute, the wacky friends, the lovable stars with electric chemistry and a skill for adorably awkward entanglements. (In what world would anyone say “no” to having orange juice spilled on them by a 1990s Hugh Grant?) In fact, Notting Hill exceeds these conventions to a degree that, in any other film, might have been cloying and excessive. (Really, there are multiple meet-cutes; Hugh Grant is exceedingly awkward.) But thanks to its stars, as well as the careful writing by Richard Curtis, who had made magic with Grant in Four Weddings and a Funeral just a few years before, Notting Hill hits all the requisite notes just right. —Laura Bradley

6. Groundhog Day (1993)

Groundhog Day is the ultimate rom-com for curmudgeons who don’t like rom-coms, the perfect salve for a hardened cynic’s heart. After all, its hero is himself exquisitely sour: Phil Connors, a weatherman sent to Punxsutawney, P.A., to cover the pointless annual ritual of a groundhog looking for its shadow, may be Bill Murray’s ideal role. Bored with life, he gets caught in a time loop in which he’s repeatedly forced to relive the previous 24 hours. That means that day after day, he gets turned down by his producer, Rita, played with twinkly self-possession by Andie MacDowell. By dilating each moment, the movie expands Phil’s sense of wonder exponentially. He gets to know the inhabitants of this tiny town, to learn kindness and curiosity. And the repetition of time gradually washes away his misery and egotism. Phil spends a big chunk of the movie trying to figure out fraudulent ways to seduce Rita, but it’s only when he stops trying to trick her into bed and has fun being with her (and he, in turn, becomes a human being she can enjoy) that the romance clicks. It’s an amazing emotional and structural feat, a movie that I would happily watch again and again and again. —Joy Press

5. 10 Things I Hate About You (1999)

10 Things is right on the line between teen movie and romantic comedy, but what elevates this film past high-school drama is the mature performances from Julia Stiles and the late, great Heath Ledger, who personify the frustration of being over high school but too young for college in separate, equally winning ways. In a way, the incredibly juvenile premise—a spin on Shakespeare’s Taming of the Shrew in which Ledger’s character is paid to take out Stiles’s, so that a whole other set of characters can go out with her younger sister—is just there to be transcended, as sparks fly between two people who had long ago given up on this dumb school (and, by extension, this dumb town). Joseph Gordon-Levitt, David Krumholtz, Susan May Pratt, and Larisa Oleynik round out the cast for an especially endearing view of high-school power dynamics and the banal cruelties of teenage heartbreak. All that, plus a public display of affection on a football field using Frankie Valli’s “Can’t Take My Eyes Off of You.” —Sonia Saraiya

4. Bridget Jones’s Diary (2001)

For anyone who’s ever found herself sitting at home with dangerous quantities of wine and cake, belting out “All by Myself” alone, this one was bound to be a home run—and apparently, quite a lot of us could relate. Renée Zellweger’s hapless heroine Bridget Jones and her competing love interests—played with distinctly British charm by Colin Firth and Hugh Grant—became an instant hit in 2001. Although the sequels never lived up to the promise of the original, it’s hard to think of anything that could erase the legacy of blue soup, ugly Christmas sweaters, and embarrassing fights in the street. Besides, it’s hard to think of a more satisfyingly absurd, distinctly “rom-com” climax than the moment Bridget chases Mr. Darcy down a snowy London street in nothing but a pair of sneakers, a jacket, and zebra-print undies. —Laura Bradley

3. Clueless (1995)

In adapting Jane Austen’s Emma, about a scheming matchmaker surprised by her own romance, for mid-90s teenagehood, writer-director Amy Heckerling invented her own idiom. Baldwins, Monets, and Cake Boys all swirl happily in the orbit of Cher Horowitz, a shallow Beverly Hills princess of hidden depth played brilliantly by Alicia Silverstone in a generation-defining performance. (There would be no Regina George without Cher.) Heckerling’s world—which includes an adorable Paul Rudd as a just slightly problematic love interest—is lively and silly, but also sharp. The movie’s critique and veneration of teen culture may look quaint in this era of Instagram stars, but Clueless still stands sturdily in its platform sneakers as one of the best of the genre—of several genres, in fact. Has there ever been a better teen comedy? As if. —Richard Lawson

2. You’ve Got Mail (1998)

You’ve Got Mail is the last of Nora Ephron’s genre-defining romantic comedies, arriving in theaters after When Harry Met Sally and Sleepless in Seattle, but before the new millennium. It’s the second film Ephron made with Meg Ryan and Tom Hanks, who circle each other easily as sparring partners Kathleen Kelly (who owns the Shop Around the Corner children’s book store) and Joe Fox (who runs the capitalist scourge Fox & Sons Books). They fall in love, using technology that would eventually put both characters out of business if cameras kept rolling for another decade: the Internet. Though a film about romance in the age of America Online was always going to be hopelessly dated, it was also the first rom-com to normalize the thrill of flirting via chat box with an anonymous stranger (even while talking about innocuous things like butterflies and buying school supplies in the fall). It was the first rom-com to cast Dave Chappelle as a best friend; the first to use a dial-up modem as the opening credits song; and the first to playfully skewer how easy it is to catfish a potential mate. And while it also wasn’t the first romantic comedy to have its male character gaslight his love interest, Fox does come clean about it in the end. —Kenzie Bryant

1. When Harry Met Sally (1989)

It launched the rom-com career of the singular Nora Ephron. It established Meg Ryan as America’s sweetheart. And it became the gold standard that Hollywood tried to emulate for the next decade. 1989’s When Harry Met Sally and all its talky, charming smartness felt revelatory upon its release, and still resonates today primarily because it so thoughtfully examines the central question posed at the beginning: can (straight) men and women really be just friends? While those stark gender lines, and Sally’s obsession with marriage, feel a bit dated in 2018, the film is still a near perfect execution of the genre. Ephron and director Rob Reiner achieve that alchemy by combining the sweet quirkiness of Ryan’s Sally Albright with the cranky pessimism of Billy Crystal’s Harry Burns, all swirled together with Ephron’s endlessly quotable dialogue (as well as more than a few memorable improvised lines): “Baby Fish Mouth is sweeping the nation!”; “Waiter, there is too much pepper on my paprikash!” Of course, you also can’t forget the charming faux-documentary vignettes of longtime married couples sprinkled throughout the piece, and the stellar supporting performances by Carrie Fisher and Bruno Kirby. Re-watching the film today is a bleak reminder of all that on- and off-screen talent that is no longer here—but thankfully, Ephron’s intelligent wit, and those who sold it, will live on forever. “I’ll have what she’s having.” —Nicole Sperling

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