Reports of the death of the romantic comedy have been greatly exaggerated. Sure, the always endangered genre has lost some of its luster since its heyday in the 1990s. But even now, audiences are still hungry for witty banter, unexpected meet-cutes, and a happy ending. Streaming platforms like Netflix and Max have released scores of rom-coms; Anyone But You made bank at the box office in 2023; Bridget Jones: Mad About the Boy recently made our critic’s list of the best movies of 2025 so far.
broad definition of what it takes to be a romantic comedy. Rom-coms are, by definition, “a genre in which the development of a romance leads to comic situations.” So grab your popcorn and take a gander at Vanity Fair’s 42 favorite romantic comedies of all time.
42. Red, White, and Royal Blue (2023)
The ’90s had My Date With the President’s Daughter, and the 2020s has My Date With the President’s Son. Based on the 2019 novel of the same name by Casey McQuiston, Red, White, and Royal Blue follows the unlikely romance between Alex Claremont-Diaz (Taylor Zakhar Perez) and Prince Henry (Nicholas Galitzine). The fact that they’re both guys isn’t the only thing that makes their courtship difficult: Alex is the aforementioned president’s son, and Henry happens to be third in line for the British throne. Their international affair may quite literally affect international affairs. Directed by Tony winner Matthew López, Red, White and Royal Blue is both a queer romance and a White House romp. Galitzine and Perez are charming as the two lovebirds, discovering their sexuality on a very public stage. The film also features a daffy performance from Uma Thurman as a very Southern president of the United States. — Chris Murphy
41. But I’m a Cheerleader (1999)
Julia Roberts wasn’t the only redheaded rom-com actress of the ’90s. There was also Natasha Lyonne, delivering a wonderful performance in the campy and fun lesbian rom-com But I’m a Cheerleader. In the film by Jamie Babbit, Lyonne stars as Megan, a closeted cheerleader sent to conversion-therapy camp by her parents. While this may not sound like the best setting for a romantic comedy, she meets a host of other closeted teens there—including the edgy and cool Graham (Clea DuVall), who captures her heart. But I’m A Cheerleader also boasts a hilarious performance by none other than RuPaul, playing a counselor at the conversion-therapy camp who may be struggling with many of the same issues his campers are. For anyone looking for truly comic yet surprisingly sincere exploration of queerness with a happy ending, But I’m a Cheerleader is the girl for you. — Chris Murphy
40. 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
39. Sweethearts (2024)
Sometimes the greatest love of all is actually your best friend. In Sweethearts, a Max romantic comedy from Jordan Weiss, college BFFs Ben (Nico Hiraga) and Jamie (Kiernan Shipka) make a pact to break up with their respective partners while they’re both home for Thanksgiving break. Of course, that’s easier said than done. Sweethearts is a sweet look at love and friendship and the many ways they intertwine. It also boasts a standout performance from comedian and podcaster Caleb Hearon, who steal scenes as Palmer, Ben and Jamie’s gay best friend. —Chris Murphy
38. Anyone But You (2023)
Shakespeare really knew how to write a romantic comedy, didn’t he? Loosely based on the Shakespearean comedy Much Ado About Nothing, Anyone But You stars Sydney Sweeney and Glen Powell as Bea and Ben, a modern-day Beatrice and Benedick. Despite having an amazing first date, Bea and Ben’s initial attraction quickly turns sour. When they unexpectedly find themselves at a destination wedding in Australia, the pair pretend to be the perfect couple for contrived reasons—but in the process, they find out that there’s a fine line between love and hate The film was a sleeper hit, earning $220 million worldwide. It might have helped that the world was also quite interested in Sweeney and Powell’s off-screen relationship, with rumors of romance circling the rising stars. Based on Anyone But You, it’s undeniable that the pair has chemistry. — Chris Murphy
37. 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
36. 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
35. 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
34. The Wedding Banquet (2025)
Here comes the bride, and a new Wedding Banquet. Fire Island filmmaker Andrew Ahn re-teamed with Saturday Night Live’s Bowen Yang to remake Ang Lee’s fabulous 1993 wedding comedy, which centered 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. In Ahn’s remake, The Wedding Banquet now follows two queer couples in Seattle: Yang’s Chris and Min (Hang Gi-chan), and Angela and Lee, played by Kelly Marie Tran and Oscar nominee Lily Gladstone. When the Korean Min’s student visa is about to expire, Min and Lee hatch a plan: Min should marry Angela for a green card, and in exchange, Chris and Min will pay for Lee’s fertility treatments. What could possibly go wrong? Ahn’s Wedding Banquet remake was positively received, proving that adding a modern touch to the best romantic comedies is always a winning formula.—Chris Murphy
33. 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
32. Bridget Jones: Mad About the Boy (2025)
Renée Zellweger’s hapless yet winning British heroine returned to the silver screen once again in Bridget Jones Diary: Mad About the Boy. The fourth film in the beloved franchise finds Jones a single mom in London, raising two children and still grieving the loss of her husband, Mark Darcy (Colin Firth)—who has been killed during a humanitarian mission in Sudan. Michael Morris’s movie really takes off when Bridget falls head over heels (sometimes literally) for a younger man: Roxster, played by White Lotus breakout Leo Woodall. She also keeps having chance encounters with her children’s science teacher, Mr. Walliker, portrayed by Chiwetel Ejiofor. As Bridget navigates the pitfalls (and pratfalls) of middle-aged romance, we catch up with some of our favorite friends from Bridget Jones films of yore, including Dr. Rawlings (Emma Thompson) and Daniel Cleaver—now Uncle Daniel, but still played with devilish charm by Hugh Grant. Zellweger’s performance is as endearing as ever; watching this movie, you can’t help but root for Bridget Jones to get her groove back. – Chris Murphy
31. 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
30. Emma (2020)
You don’t get Clueless without Emma. Jane Austen’s seminal novel brings us into the world of Emma Woodhouse, a girl who’s “handsome, clever, and rich”—and can’t help but matchmake and meddle in the lives of her friends and neighbors. In 2020, Anya Taylor Joy played the titular role in a new film adaptation that allowed the star of The Witch to show a whole new side of herself as the daffy, well-intentioned but sometimes vain teen heroine. She would soon go on to star in The Queen’s Gambit and cement herself as an A-list talent. In Emma, she’s matched by a wonderful ensemble of actors including Johnny Flynn, Josh O’Connor, Mia Goth, and Bill Nighy as her overly cautious father, Mr. Woodhouse. If you’ve binged all of Bridgerton and are in need of some more Regency-era England, Emma is waiting for you.— Chris Murphy
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’s 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’s 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’s 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’s 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
28. 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’s Maude—a lively septanagerian who forces her younger counterpart to acknowledge life’s beauty—enters the picture. Like its titular characters, the movie is both sweet and sour in its depiction of the pair’s 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’s inevitable death feel oddly uplifting. —Savannah Walsh
27. The Idea of You (2024)
Who hasn’t dreamed of meeting a pop star at a music festival, then having them fall head-over-heels for you? That’s exactly what happens to Anne Hathaway in The Idea of You. Based on the book of the same name, Hathaway stars as Solène, a divorced art gallerist living in Los Angeles. When she takes her teen daughter to Coachella, she stumbles into the wrong trailer and has a meet-cute with Hayes Campbell—a member of the extremely popular boy band August Moon, played by Nicholas Galitzine. Despite a bit of an age gap, sparks fly between Solène and Hayes, and a May-December romance begins. Directed by Michael Showalter, The Idea of You is fun and flirty, and showcases Hathaway at her best—charming, wry, and emotionally available. It also helps that the August Moon songs written by Savan Kotecha are legitimately catchy, and Galitzine pulls off his Harry Styles—esque pop star character with aplomb. The Idea Of You is the perfect rom-com for anyone with a song in their heart. — Chris Murphy
26. Enchanted (2007)
In retrospect, it’s 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’s straight-and-narrow divorce lawyer Robert. What could’ve been mawkish is grounded by the pair’s 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
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’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
24. 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
23. 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
22. 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
21. 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
20. How Stella Got Her Groove Back (1998)
In Hollywood, leading men are often much older than their female love interests, but it’s 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’s frontrunner status at the 2023 Oscars, the time for a rewatch (or introduction) is now. —Savannah Walsh
19. Anora (2024)
We know what you’re thinking… Is Anora really a romantic comedy? But hear us out. Sean Baker’s 2025 Oscar best-picture winner—starring surprise best-actress winner Mikey Madison as a sex worker from Brighton Beach who falls for Vanya (Mark Eydelshteyn), the immature son of a Russian oligarch, then embarks on a whirlwind romance—certainly isn’t a traditional exemplar of this genre. While there are plenty of laughs to be had, Ani and Vanya’s dream of a relationship soon becomes a nightmare. But the trick of Anora is that the real romance isn’t between Ani and Vanya: it’s between Ani and Igor, a quiet but wise member of Vanya’s security team tasked played by Oscar nominee Yura Burisov. Ani and Igor’s relationship is surprising and unexpected, sneaking up on you over the course of the film. Eventually, it becomes evident that Ani’s knight in shining armor may have been standing beside her all along. A modern-day Pretty Woman with a ton of laughs and an ambiguous but arguably sweet ending? Yes, Anora earns a spot on this list. — Chris Murphy
18. 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 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’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
17. 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
16. 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
15. 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
14. 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
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’s lightning-in-a-bottle synergy. —Savannah Walsh
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’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
11. Phantom Thread (2017)
Let the record show that Daniel Day Lewis’s (allegedly) final film role was in his first romantic comedy. On the surface, Paul Thomas Anderson’s 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’s even a When Harry Met Sally-esque New Year’s Eve scene. Reimagined as an ‘80s romantic comedy, nothing about Phantom Thread’s core DNA changes. As Vanity Fair’s Richard Lawson, who deemed it “the most surprising love story” of 2017, concludes, “There’s 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’s fiercely romantic, in its improbable way.” —Savannah Walsh
10. What’s 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’s 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’s well-executed indignity steals the scene—and threatens to run away with the whole movie. —Savannah Walsh
9. Love & Basketball (2000)
They don’t often come as irresistible or instantly rewatchable as Love & Basketball, Gina Prince-Bythewood’s 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’s 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
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’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
7. Roman Holiday (1953)
One could credit or blame this film for inspiring everything from The Prince and Me to Netflix’s The Princess Switch franchise. The well-worn formula began with Audrey Hepburn’s 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’s 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’s deceit is revealed and the reality of their different stations in life comes rushing back into focus. The film’s final scene remains one of the most quietly heartbreaking in romantic comedy history. Directed by William Wyler, Roman Holiday would prove to be Hepburn’s own crowning achievement, earning her an Oscar for best actress in the process. —Savannah Walsh
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’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
5. 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
4. Bridget Jones’s Diary (2001)
To kick off a four film franchise, the first movie out of the gate has to have the juice—and Bridget Jone’s Diary certainly does. 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—that is until the fourth one came along—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
The post The 42 Best Romantic Comedies of All Time appeared first on Vanity Fair.
