“I’ll have what she’蝉 having”

The 42 Best Romantic Comedies of All Time

We take stock of the best rom-coms ever—from Coming to America to Groundhog Day to three Nora Ephron classics.
This image may contain Advertisement Collage Poster Human and Person
Photo Illustration by Lauren Margit Jones; Photos, from left, by Sophie Giraud/Ifc/Kobal, from Castle Rock/Nelson/Columbia/Kobal, both from REX/Shutterstock; From Paramount/Everett Collection.

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’蝉 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’蝉 Day offers two heart-on-their-sleeves rom-coms. Genre stalwart?Aline Brosch McKenna?(Crazy Ex-Girlfriend,?27 Dresses) makes her directorial debut with?狈别迟蹿濒颈虫’蝉?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’蝉?My Best Friend’蝉 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’蝉 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’蝉?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’蝉 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’蝉 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’蝉 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’蝉 really just a red herring,” Wu told Vanity Fair of her film’蝉 outcome. “Who gets the girl—not only is it not the important thing in this movie, it’蝉 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

By Sophie Giraud/IFC Films/Photofest.

40. My Big Fat Greek Wedding (2002)

The joy of My Big Fat Greek Wedding, starring and written by Nia Vardalos, is that it’蝉 actually several films baked into one. Romance! Comedy! Culture shock! The secret healing powers of Windex! Vardalos’蝉 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’蝉 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’蝉 the romance, which Vardalos pens so sweetly, that grounds it all. We trace Toula and Ian’蝉 relationship from the very first time they lay eyes on each other, all the way to Ian’蝉 intimate proposal. A film this big and sweeping needs an anchor, and these two do quite nicely. —Yohana Desta

From Columbia Pictures/Photofest.

39. Something’蝉 Gotta Give (2003)

Here’蝉 a little ditty about Jack (Nicholson) and Diane (Keaton), the silver-haired leads of Nancy Meyers’蝉 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’蝉 character takes Nicholson’蝉 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

? 20th Century Fox/Everett Collection.

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

?Geffen Pictures/Courtesy Everett Collection

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’蝉 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’蝉 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

? Paramount/Everett Collection.

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’蝉 man is undeniable even though their romance is doomed from the start. She’蝉 a writer at a women’蝉 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’蝉 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’蝉 basically impossible to do anything but cheer. —Laura Bradley

NEVER BEEN KISSED, (L-R): Drew Barrymore, Leelee Sobieski, 1999.Courtesy of 20th Century Fox/ Everett Collection.

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’蝉 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’蝉 premise endures. So much so that Barrymore often reprises the role for segments on her similarly spirited daytime talk show. —Savannah Walsh

? Paramount/Everett Collection.

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’蝉 Keith (an artsy outcast), Mary Stuart Masterson’蝉 Watts (his tomboyish best friend), and Lea Thompson’蝉 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’蝉 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’蝉 director, Howard Deutch, who met on the film. —Anna Lisa Raya

CRAZY RICH ASIANS, Michelle Yeoh, 2018.By Sanja Bucko /Warner Bros. Pictures /Courtesy Everett Collection.

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’蝉 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’蝉 sparkling adaptation of Kevin Kwan’蝉 bestselling novel, centered on the love story between Rachel (Constance Wu) and Nick (Henry Golding)—and how their romance is tested by the latter’蝉 exorbitantly wealthy, slightly unhinged family. Every frame bursts with opulence, from Michelle Yeoh’蝉 steely performance as Nick’蝉 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

From Everett Collection.

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’蝉 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

By Sam Goldwyn/Renaissance/BBC/Kobal/REX/Shutterstock.

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

30. 础尘é濒颈别 (2001)

It’蝉 not a movie that many would traditionally classify as a romantic comedy, but 础尘é濒颈别 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 br?lée, 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 础尘é濒颈别 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’蝉 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. 础尘é濒颈别’蝉 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

Photo by Sarah Shatz

29. The Big Sick (2017)

One of the most refreshing rom-coms in recent years was inspired by the real-life courtship between star Kumail Nanjiani and his wife, Emily V. Gordon, with whom he wrote the film’蝉 screenplay. In the movie, their burgeoning relationship is stopped dead in its tracks when Emily (played onscreen by Zoe Kazan) experiences a major medical crisis and falls into a coma. While she’蝉 sleeping, Kumail attempts to bond with his future in-laws (a perfectly-matched Holly Hunter and Ray Romano) and contend with the cultural obstacles he faces as a Muslim, Pakistani man who wants to forego his family’蝉 plans for an arranged marriage. “It sounds so serious on paper: A Pakistani guy whose parents want him to have an arranged marriage has his white girlfriend go into a coma,” Nanjiani told Entertainment Weekly upon the project’蝉 release. “But it is a comedy!” Produced by Judd Apatow and directed by Michael Showalter, the tonally trick film earned Nanjiani and Gordon a best original screenplay Oscar nomination and helped reinvigorate the genre. —Savannah Walsh

HOW STELLA GOT HER GROOVE BACK, (L-R): Taye Diggs, ?Angela Bassett, 1998.Courtesy 20th Century Fox.

28. How Stella Got Her Groove Back (1998)

In Hollywood, leading men are often much older than their female love interests, but it’蝉 still a rarity to see that reversal for women on screen. Enter Stella and her need to reclaim that titular groove. Angela Bassett stars as a woman in search of her next great adventure, coerced into a tropical getaway by her best friend Delilah (a perfectly cast Whoopi Goldberg), and swept off her feet by Taye Diggs, a younger island local who urges her to set fear about their (retrospectively pretty tame) age gap aside. What follows is a fun, sexy, proto-Eat Pray Love-style romp that still manages to pack an emotional punch. In honor of Bassett’蝉 frontrunner status at the 2023 Oscars, the time for a rewatch (or introduction) is now. —Savannah Walsh

Courtesy Everett Collection

27. Harold and Maude (1971)

One of the most unconventional yet life-affirming comedies ever made comes from auteur Hal Ashby. Bud Cort stars as Harold, a troubled youth whose fascination with death colors his entire worldview. That is, until Ruth Gordon’蝉 Maude—a lively septanagerian who forces her younger counterpart to acknowledge life’蝉 beauty—enters the picture. Like its titular characters, the movie is both sweet and sour in its depiction of the pair’蝉 bizarre friendship. While the couple spends most of the film having philosophical chats and walking through fields of flowers, their dark ending looms. But leave it to Ashby to make even a character’蝉 inevitable death feel oddly uplifting. —Savannah Walsh

ENCHANTED, Amy Adams, 2007.?Courtesy of Buena Vista Pictures/Everett Collection.

26. Enchanted (2007)

In retrospect, it’蝉 sort of a miracle that anything about this (mostly) live-action spin on the Disney princess works. So much of it is an uphill battle—long segments are told via old-school animation; there are several splashy musical numbers (some of which feature singing vermin); and the ending hinges on a truly frightening sequence involving Susan Sarandon dressed as an evil hag, then disguised as a CGI dragon. Yet the biggest victory may be in selling the romance between Amy Adams’ Gisele (who, again, is a cartoon princess brought to life) and Patrick Dempsey’蝉 straight-and-narrow divorce lawyer Robert. What could’ve been mawkish is grounded by the pair’蝉 crackling chemistry and rounded out with a downright award-worthy performance by James Marsden as the Prince Charming who was never destined to get the girl.? —Savannah Walsh

From Everett Collection.

25. 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’蝉 in love with a married man. It’蝉 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’蝉 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’蝉 building, will even wind up together. We’re not even sure it’蝉 a question worth asking—it’蝉 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’蝉 one of the great workplace comedies—a movie worth watching again with fresh eyes. —K. Austin Collins

? Gramercy Pictures/Everett Collection.

24. 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’蝉 wedding? Everything about Richard Curtis’蝉 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’蝉 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’蝉 a messy romp that opened up territory for decades of rom-coms to come. —Joy Press

? MGM/Photofest.

23. 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’蝉 genre-snob voters fell victim to its charm. (In addition to Shanley’蝉 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’蝉 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

22. 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’蝉 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’蝉 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’蝉 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’蝉 radars. —Julie Miller

Courtesy Everett Collection

21. The Shop Around the Corner (1940)

There would be no You’ve Got Mail without Ernst Lubitsch’蝉 The Shop Around the Corner, which inspired both Kathleen Kelly’蝉 Upper West Side bookstore and the 1998 film’蝉 central structure. In Shop, our two leads aren’t warring business competitors, but instead a pair of squabbling salesclerks in a Budapest department store who don’t know they’re secret pen pals. Set during the holiday season, this film often gets short shrift as the second best Christmas movie starring James Stewart. But the understated charms of Shop are not to be ignored. Margaret Sullivan’蝉 Klara is a worthy sparring partner for Stewart’蝉 Alfred. Fresh off his turn as the titular role in The Wizard of Oz, Frank Morgan delivers a scene-stealing turn as store boss Hugo Matuschek. And a running joke involving the shop’蝉 musical cigarette boxes pays off with each rewatch. —Savannah Walsh

? 20th Century Fox/Everett Collection.

20. Down with Love (2003)

Peyton Reed’蝉 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’蝉 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’蝉 proto-feminist attempt to get women to live and fall in 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’蝉 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

THE WEDDING BANQUET, (aka HSI YEN), May Chin, Winston Chao, 1993.Courtesy of Samuel Goldwyn Films/Everett Collection.

19. The Wedding Banquet (1993)

Oscar-winning filmmaker Ang Lee is typically lauded for his visual prowess, thanks to lush films like Life of Pi and Crouching Tiger, Hidden Dragon. But he’蝉 sneakily one of the best directors of romance as well (see: 1995’蝉 Sense and Sensibility and 2005’蝉 Brokeback Mountain). That brings us to an Oscar-nominated rom-com from earlier in Lee’蝉 filmography, which centers on a closeted Taiwanese man in a long-term relationship who agrees to an arranged marriage with a woman in order to satisfy his traditional parents. An already thorny situation is further complicated when the bride-to-be reveals the secret she hopes to protect with their union. Things only get more twisty from there, leading to an ending that is deliciously surprising—and particularly subversive—for 1993. —Savannah Walsh

From Everett Collection.

18. 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’蝉 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’蝉 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

? Sony Pictures Entertainment/Photofest.

17. My Best Friend’蝉 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’蝉 Wedding.) In P.J. Hogan’蝉 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’蝉 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’蝉 Wedding makes its most salient observation: sometimes it’蝉 friendship, not romance, that rescues us—and redeems us, too. —Richard Lawson

By Bruce McBroom/Tri-Star/Kobal/REX/Shutterstock.

16. Sleepless in Seattle (1993)

Come for Nora Ephron’蝉 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’蝉 (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’蝉 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’蝉 long-awaited meet-cute atop the Empire State Building. —Nicole Sperling

By Kerry Hayes/20th Century Fox/Kobal/REX/Shutterstock.

15. 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’蝉 character, a TV news producer, is as smart and honorable as her best friend, a journalist played by Albert Brooks. But she’蝉 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

THE PRINCESS BRIDE, from left; Cary Elwes, robin Wright, 1987,Courtesy of 20th Century Fox Film/Everett Collection.

14. The Princess Bride (1987)

As you wish. The utterance of those three words is all the evidence needed for why Rob Reiner’蝉 adaptation of William Goldman’蝉 novel is one of the best romantic comedies of all time. Cary Elwes loads them with chemistry when whispering as Westley to Robin Wright’蝉 Buttercup. They later incite laughter and shock when chanted down a hill. And when said by the all-too-comforting Peter Falk in the film’蝉 final moments, it’蝉 nearly impossible to ward off the goosebumps. There are a whole bunch of other brilliant lines in between—from Wallace Shawn (“滨苍肠辞苍肠别颈惫补产濒别!”), Billy Crystal (“Have fun storming the castle!) and Mandy Patinkin (“Hello my name is Inigo Montoya. You killed my father. Prepare to die”), among others. The movie built around them is why we’re still reciting all these decades later. —Savannah Walsh

?Paramount/Courtesy Everett Collection

13. Coming to America (1988)

Eddie Murphy enjoyed a string of comedic hits in the ‘80s, including Trading Places and Beverly Hills Cop—but no vehicle captures him at the height of his powers like Coming to America. Murphy plays Prince Akeem, a royal heir who finds himself disillusioned with life in his African country and journeys to Queens, New York in pursuit of a wife who can be his equal. Thanks to prosthetics from makeup artist Rick Baker, Murphy and his co-star Arsenio Hall take on multiple supporting roles in the film, which also stars Shari Headley as his one true love. The enduring love for Coming to America spawned a middling 2021 sequel, which only solidified the original’蝉 lightning-in-a-bottle synergy. —Savannah Walsh

From Everett Collection.

12. 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 falling in 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’蝉 enterprising reporter. Their relationship is sparring and hilarious, the two clearly perfectly matched in wits, until it turns irrepressibly romantic, with Colbert’蝉 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

11. 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’蝉 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

Courtesy Everett Collection

10. Roman Holiday (1953)

One could credit or blame this film for inspiring everything from The Prince and Me to Netflix’蝉 The Princess Switch franchise. The well-worn formula began with Audrey Hepburn’蝉 Princess Ann fleeing from her gold-plated prison for adventure in the Eternal City. While taking her trip on the wild side, she encounters American journalist Joe Bradley (a smoldering Gregory Peck), who takes his royal run-in as the perfect opportunity for an explosive article. Hepburn and Peck’蝉 chemistry is undeniable, and watching them fall in love while riding a Vespa or grazing near the Trevi fountain is a breezily comforting affair. That is, until Joe’蝉 deceit is revealed and the reality of their different stations in life comes rushing back into focus. The film’蝉 final scene remains one of the most quietly heartbreaking in romantic comedy history. Directed by William Wyler, Roman Holiday would prove to be Hepburn’蝉 own crowning achievement, earning her an Oscar for best actress in the process. —Savannah Walsh

LOVE AND BASKETBALL, Omar Epps, Sanaa Lathan, 2000,?Courtesy of New Line Cinema/Everett Collection.

9. Love & Basketball (2000)

They don’t often come as irresistible or instantly rewatchable as Love & Basketball, Gina Prince-Bythewood’蝉 hoops-heavy fairytale starring Sanaa Lathan as Monica Wright—an aspiring basketball player who falls in love with her neighbor and childhood confidant Quincy, played by Omar Epps. Nearly 25 years later, Prince-Blythewood told Vanity Fair (via Gabrielle Union, who stars as one of Quincy’蝉 other love interests) that her first film “absolutely set the tone” for the dynamic career that would follow. “I think it is so important for your first film to do that, to reflect who you are, say who you are, introduce yourself,” she continued. “Which is why I'm so glad it was Love & Basketball and not something I had almost done.” Consider us similarly grateful. —Savannah Walsh

? Columbia Pictures/Everett Collection.

8. 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’蝉 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’蝉 ideal role. Bored with life, he gets caught in a time loop in which he’蝉 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’蝉 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’蝉 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’蝉 an amazing emotional and structural feat, a movie that I would happily watch again and again and again. —Joy Press

Courtesy Everett Collection

7. What’蝉 Up, Doc? (1972)

This Bringing Up Baby-esque slapstick comedy is made picture-perfect thanks to the onscreen trifecta of Barbra Streisand as freewheeling college dropout Judy Maxwell, Ryan O’Neal as uptight musicologist Dr. Howard Bannister, and Madeline Kahn in her first onscreen role as Howard’蝉 shrill fiancée Eunice Burns. Their performances soar under the direction of Peter Bogdonavich, working from a quick-witted script by Graduate cowriter Buck Henry and Bonnie and Clyde cowriters David Newman and Robert Benton. The enduring legacy of Doc remains its comedic set pieces, including an elaborate car chase through the hills of San Francisco and a sequence in which Howard pretends not to know Eunice in a restaurant while hiding beneath a table with Judy. Khan’蝉 well-executed indignity steals the scene—and threatens to run away with the whole movie. —Savannah Walsh

? Buena Vista/Photofest.

6. 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’蝉 Taming of the Shrew in which Ledger’蝉 character is paid to take out Stiles’蝉, 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’蝉 “Can’t Take My Eyes Off of You.” —Sonia Saraiya

PHANTOM THREAD, from left: Vicky Krieps, Daniel Day-Lewis, 2017.?By Laurie Sparham /Focus Features /Courtesy Everett Collection.

5. Phantom Thread (2017)

Let the record show that Daniel Day Lewis’蝉 (allegedly) final film role was in his first romantic comedy. On the surface, Paul Thomas Anderson’蝉 meditation on marriage is too deranged and dark to be considered alongside the works of Nancy Meyers or Nora Ephron. But look more closely, and you’ll see that the budding relationship between Reynolds Woodcock (Day-Lewis), a renowned dress designer in 1950s London, and Alma, (Vicky Krieps) an unassuming waitress decades his junior, fits the rom-com formula. Alma literally trips upon her awkwardly endearing meet-cute with Reynolds; they spar over their opposing lifestyles and backgrounds; there’蝉 even a When Harry Met Sally-esque New Year’蝉 Eve scene. Reimagined as an ‘80s romantic comedy, nothing about Phantom Thread’蝉 core DNA changes. As Vanity Fair’蝉 Richard Lawson, who deemed it “the most surprising love story” of 2017, concludes, “There’蝉 a ‘you and me babe, against the world’ kind of vibe to Phantom Thread—it winks with the conspiratorial coziness of a private joke. It’蝉 fiercely romantic, in its improbable way.” —Savannah Walsh

From Miramax Films/Photofest.

4. Bridget Jones’蝉 Diary (2001)

For anyone who’蝉 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’蝉 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’蝉 hard to think of anything that could erase the legacy of blue soup, ugly Christmas sweaters, and embarrassing fights in the street. Besides, it’蝉 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’蝉 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’蝉 world—which includes an adorable Paul Rudd as a just slightly problematic love interest—is lively and silly, but also sharp. The movie’蝉 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

? Warner Bros/Everett Collection.

2. You’ve Got Mail (1998)

You’ve Got Mail is the last of Nora Ephron’蝉 genre-defining romantic comedies, arriving in theaters after When Harry Met Sally and Sleepless in Seattle, but before the new millennium. It’蝉 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’蝉 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

From Castle Rock/Nelson/Columbia/Kobal/REX/Shutterstock.

1. When Harry Met Sally (1989)

It launched the rom-com career of the singular Nora Ephron. It established Meg Ryan as America’蝉 sweetheart. And it became the gold standard that Hollywood tried to emulate for the next decade. 1989’蝉 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’蝉 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’蝉 Sally Albright with the cranky pessimism of Billy Crystal’蝉 Harry Burns, all swirled together with Ephron’蝉 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’蝉 intelligent wit, and those who sold it, will live on forever. “I’ll have what she’蝉 having.” —Nicole Sperling