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The 50 Best Rom-Coms

From ‘My Big Fat Greek Wedding’ to ‘Forgetting Sarah Marshall’ to ‘Sleepless in Seattle,’ here’s the best of an endlessly watchable genre

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When you find a theme week you want to spend the rest of your life with, you want the rest of your life to start as soon as possible. Thankfully, The Ringer hereby dubs this week Rom-Com Week, a celebration of one of the most delightful, captivating genres in film. Head to the top of the Empire State Building, order what she’s having, and join us as we dig into everything the rom-com has had to offer over the years—beginning with, of course, this ranking of the 50 best romantic comedies in movie history.


50. 500 Days of Summer

Much like its main plot device, the reception of 500 Days of Summer feels dependent on time. Ask someone how they felt about the movie in 2009 and they might call it the most original rom-com in decades. These days though, that response might elicit mockery: the stylish edits and vintage clothing go only so far in obscuring some highly questionable character development. “If you took out the gimmick and watched these scenes in order, you’d see it’s about a codependent stalker and the empty vessel he latches onto,” a classic Honest Trailer hilariously concludes. But to 500 Days’ credit, the film was upfront from the beginning that it was “not a love story.” In fact, honesty may be the best trait about this nuanced dramedy: The characters may not deserve sympathy, but for a lot of viewers, the story is relatable—whether they’re the Tom or Summer of a relationship. Look no further than the “Expectations vs. Reality” scene, a bitter climax that most of us would admit to experiencing in some form. —Aric Jenkins

49. To All the Boys I’ve Loved Before

There may be no better endorsement for a rom-com than when the entire internet falls in love with your lead overnight. In this case, that would be Peter Kavinsky (Noah Centineo), a charming lacrosse player who establishes a fake relationship with shy outcast Laura Jean (Lana Condor) to make his ex jealous before promptly falling for her. More refreshing than Centineo’s on-screen charisma, however, is the way TATBILB celebrates Laura Jean’s cautious individuality, leading her to her very first real-life romantic connection at exactly the pace she chooses. —Alyssa Bereznak

48. Sweet Home Alabama

Sweet Home Alabama belongs to the glorious era between You’ve Got Mail and Knocked Up, when rom-com premises were stretching the limits of credulity to stay within the boundaries of the genre before a movie came along and made realism de rigueur. Is it completely ridiculous that this movie hinges on a man’s years-long refusal to sign divorce papers? Or that the not-quite-ex-husband (Josh Lucas) is a “lightning glass” mogul? Or that Reese Witherspoon’s Melanie allegedly blew up a cat as a teenager and definitely outed one of her friends as an adult? Or that Patrick Dempsey’s character is being groomed by his mom (Candice Bergen), the mayor of New York City, to be the president of the United States? Yes—obviously all of that is ridiculous. But it’s also delightful, in a way that only ridiculous rom-coms can be. —Andrew Gruttadaro

47. Silver Linings Playbook

Jennifer Lawrence and Bradley Cooper were already stars by the time David O. Russell’s 2012 sleeper hit came out, but Silver Linings Playbook is what established them as capital-S Serious Actors. Their performances as a young widow with a bad reputation and a garbage bag–wearing Eagles fan determined to win his ex-wife back after a stint in a mental health facility were touching, funny, and critically lauded. After the movie landed Oscar nominations in all four acting categories, with Lawrence winning for Best Actress, Lawrence and Cooper became Academy Award mainstays. Maybe they would’ve gotten there anyway, but looking back on the diner scene and the dance competition, it’s hard to deny that Silver Linings Playbook catapulted them to new levels of success. —Julianna Ress

46. Harold and Maude

At the center of any good romantic comedy is an unlikely couple that makes sense as you peel back the layers. And perhaps no couple in movie history seemed as unlikely on the surface as the titular pairing of Harold and Maude. The 1971 film follows the exploits of Harold Chasen—a morbid 19-year-old prone to faking his own death and subverting his mother’s wishes—who falls for Maude Chardin, a sunny 79-year-old concentration camp survivor who loves a good joyride. Along the way, Harold also learns to love life thanks to her. Viewed today, you can see its status as the foundation for movies like Rushmore and Licorice Pizza. But 50 years ago, audiences and critics weren’t quite ready for such a quirky story: Harold and Maude bombed at the box office, and the reviews looked worse than the receipts. (Variety wrote at the time that the movie had the “fun and gaiety of a burning orphanage.”) As time wore on, however, the film reached cult status, recouping its budget years later and retrospectively earning its deserved praise (particularly for Colin Higgins’s screenplay). It may have seemed unlikely at first, but eventually, it all made sense. —Justin Sayles

Getty Images

45. Palm Springs

Movie-watchers were lacking for good rom-coms in 2020, which is why it’s comforting that Palm Springs, at its core, uses a classic template: girl-meets-boy-who-has-some-growing-up-to-do. Of course, part of the boy’s problem here is that he’s stuck in “one of those infinite time-loop situations you might have heard about,” which makes growing up a little extra challenging. Palm Springs was a fresh take, and Samberg’s taste for the absurd is fun to watch in the context of a well-worn genre. But ultimately what makes the movie is what makes most good rom-coms: great dialogue, good chemistry, and having it all work out in the end. —Nora Princiotti

44. 10 Things I Hate About You

It is so incredibly hard to make a movie about high school that’s actually cool, but 10 Things I Hate About You makes it seem easy. The screenplay hails from legendary rom-com writing duo Kirsten Smith and Karen McCullah (with an assist from William Shakespeare and his little ditty The Taming of the Shrew) and an iconic Julia Stiles performance as Kat Stratford introduced a generation of teenage viewers to Joan Jett, open hostility toward a patriarchal society, and a comically sized copy of The Bell Jar.

Buena Vista Pictures

And Heath Ledger as Patrick Verona created the blueprint for a teen rom-com heartthrob. After all, girls don’t like boys—girls like rebels with hearts of gold who steal a microphone to sing Frankie Valli during soccer practice. In 1999, these characters were genuinely radical, their jokes legitimately funny, and 20 years later, it still holds up. There’s nothing to hate about 10 Things—not even close, not even a little bit, not even at all. —Jodi Walker

43. How to Lose a Guy in 10 Days

If anyone is still laboring under the illusion that plausibility and unpredictability are prerequisites for watchability in the realm of rom-coms, they should refresh their memory of How to Lose a Guy in 10 Days. This is a movie in which Matthew McConaughey plays a Staten Island native with a Texas accent, and the Knicks play the Kings in the NBA Finals (one game of which seems to take place at the same time and venue as a Celine Dion concert). Neither of which is less far-fetched than the central setup, which revolves around two duplicitous seducers who hook up for work-related reasons but can’t quite ditch each other, even after the truth comes out. Can a movie be said to have plot holes if its plot as a whole is this silly? That’s a rhetorical question. McConaughey and Kate Hudson have chemistry, the movie is bubbly and breezy, and no “we met under false pretenses but then legitimately fell in love” story seems like a stretch after this. When you’re in the right mood, implausibility and predictability are perks, not problems. —Ben Lindbergh

42. She’s Gotta Have It

Let’s begin by stating the obvious: The rape scene in She’s Gotta Have It was a massive mistake, and one that nearly disqualifies the film as the feminist classic that director Spike Lee envisioned it as. (In recent years, Lee has said he regrets the scene, and when he adapted the film into a Netflix series in 2017, he opted not to include the plot thread.) But despite that blight, Lee’s directorial debut remains a landmark of ’80s independent cinema and one of the most honest portrayals of young-adult romance on this list. She’s Gotta Have It is the story of Nola, a young, sexually liberated Brooklynite juggling three lovers. Eventually, the three find out about each other and compare notes—it’s predictably a nightmare, if only for the incredibly awkward foursome Thanksgiving dinner that reveals each of Nola’s suitors to be a bigger bozo than previously thought. By the end of the film, Nola is ready to give monogamy a shot. She’s Gotta Have It ends with Nola going to bed by herself, though. She discovered the most important love of all: self-love. —Sayles


41. She’s the Man

Name a better Amanda Bynes performance than the one we get in She’s the Man … I’ll wait. I don’t care what Rotten Tomatoes says, it’s a highly underrated teen rom-com. Bynes delivers in a role where she’s caught between identities, not girly enough to be a debutante but also not manly enough to be respected by her male peers. Her chemistry with a young-ish Channing Tatum is off the charts, and her exaggerated take on how girls think guys act is comedic genius (especially the tampon scene). I’m pretty sure every young girl flocked to this movie back in the day and now, it’s without a doubt worth the rewatch. —Kiera Givens

40. 13 Going on 30

Every kid fantasizes about the awesome life they’re gonna have when they grow up. Thirteen-year-old Jenna Rink actually gets to see her dream come true, but at a cost: She also turned out to be a shitty adult. It’s a fun twist on the Big template, and Jennifer Garner’s doe-eyed performance sells the earnestness of trapped-in-an-adult-body Jenna. And while she faces some harsh realities of adulthood (like finding a naked man in her shower), she also gets to go back to childhood with the knowledge that her dorky but sweet best friend grows up to be Mark Ruffalo. Their charming chemistry is what makes this movie a classic rom-com on top of a thoughtful coming-of-age story. Plus, Judy Greer! The dress! Wait, was that Brie Larson? The “Thriller” dance! 13 Going on 30 has something for all ages. —Ress

Columbia Pictures

39. Knocked Up

A seminal movie in retrospect, Knocked Up accomplished many things: It established Judd Apatow as a contemporary king of comedy adding onto the success of The 40-Year-Old Virgin; it turned Seth Rogen into a leading man and Katherine Heigl (briefly) into a leading woman; it made us realize just how incredible Paul Rudd actually is. The movie even prompted a infamous discourse on sexism that arguably kick-started the dimming of Heigl’s star, a fate that’s felt increasingly problematic with each passing year. Like most comedies from the aughts and before, Knocked Up has its share of issues. But it’s also an endearing lesson on what it means to take responsibility and what it takes to make a relationship work. Plus, Rudd and Rogen riffing about Robert DeNiro’s shoes will simply never get old. —Jenkins

38. The Best Man

Imagine finding out from a novel that your fiancée cheated on you with your best man. Are you still getting married? The Best Man may be the messiest rom-com of all time—the movie is chaotic as it follows a close-knit group of Black friends who reunite for a wedding and struggle with insecurities, success, and entanglements. Malcolm D. Lee, cousin of Spike, does a fantastic job directing a piece that explores marriage and infidelity through the eyes of men, while Taye Diggs, Terrence Howard, Morris Chestnut, Sanaa Lathan, and Nia Long deliver phenomenal performances to make the film a timeless classic. —Givens

37. The Wedding Planner

It’s surprising that Jennifer Lopez and Matthew McConaughey have yet to team up again given their on-screen chemistry and the longevity of this film that hit theaters 21 years ago. One reason why The Wedding Planner holds up decades later might be due to the fact that it’s dripping in rom-com tropes: There’s the perfectly timed meet-cute, the star-crossed lovers aspect, and then, of course, Judy Greer playing one of her career-defining best friend roles. The other reason why this movie works so well is, of course, the performances of Lopez and McConaughey. They’re both at the height of their powers—she a gorgeous, career-minded woman with a false relatability that reads as charming, he a hunky doctor with the perfect amount of mischief that beguiles us from the moment we hear that slight Southern drawl. All together, it’s rom-com magic. —Amelia Wedemeyer

36. The Cutting Edge

Turtlenecks, tequila, and TOE PIIICK: the winners’ podium of our hearts! 1992’s The Cutting Edge paired the training montages and track suits of a sports flick with the disdainful-to-disarmed chemistry of a romantic comedy, tracing the way snooty Kate Moseley and lunch-pail Doug Dorsey learn to collaborate on the ice and coexist off of it. (It also educated a generation of youths about how to create a salt lick on their wrists.) Written by Tony Gilroy, who would go on to pen Michael Clayton, Armageddon, and almost every Bourne movie, the script was brought to life by D.B. Sweeney’s hockey-inflected chirps and Moira Kelly’s haughty sputter. (No other human on Earth can mimic the way she pronounces “please don’t let me keep you from the trough;” somehow, much of the movie was shot while she had a broken foot.) Sweeney told Entertainment Weekly that in the decades since the movie’s release, “I hear ‘toe pick’ five times a day.” And honestly? For a romantic catchphrase on par with “Here’s looking at you, kid” and “You had me at hello,” that actually seems low. —Katie Baker

35. Crazy, Stupid, Love

When it comes to the scene-stealing chemistry between Ryan Gosling and Emma Stone, La La Land wants what Crazy, Stupid, Love has. Crazy, Stupid, Love was released right in the middle of Gosling’s golden era, and he spends the movie reminding us what he can do when given a solid comedic, romantic vehicle. The Stone-Gosling ‘ship isn’t even the highlight of the movie—you could argue Gosling’s chemistry with Steve Carell’s newly single dad shines even brighter, and if you haven’t seen a meme from one of the shopping scenes, you probably weren’t on the internet from 2011 through 2015. Sure, parts of the film haven’t aged particularly well, but in large part, the movie holds up. If La La Land had tossed in the lift from Dirty Dancing, maybe it would have won Best Picture after all. —Kate Halliwell

34. Bull Durham

Writer-director/former baseball prospect Ron Shelton told The Ringer in 2018 that Bull Durham is “about two people who are at a point in their lives where running into each other is forcing them to face the question they haven’t wanted to face. Is it time to stop what I’m doing and take some chances?” Crash Davis (Kevin Costner) is a career minor leaguer who has no shot at the bigs. Annie Savoy (Susan Sarandon) is an English professor who has a romance with a ballplayer every season before moving on. Naturally, they end up together.

But first, fireworks. There’s a love triangle between Annie, Crash, and phenom Nuke LaLoosh (Tim Robbins); there’s Crash’s famous monologue when he says he believes in—among other things—“long, slow, deep, soft wet kisses that last three days;” and there’s a scene when Crash paints Annie’s toenails red. There may be funnier sports movies out there–Shelton’s White Men Can’t Jump, for example—but none as romantic and sexy as Bull Durham. —Alan Siegel

33. Amélie

I remember the way I felt when I watched Amélie for the first time. Not to totally lean into the fact that this is a French film, but I’m sure that everyone reading will agree that it has a certain je ne sais quoi—from the manic pixie girl title character (her iconic bob with bangs!) to the traveling gnome secondary plot (a quirky prank from our eccentric heroine!). The story itself is flirty, whimsical, and unlike many romantic comedies nowadays, it was beloved by critics, earning five Academy Award nominations, including Best Foreign Language Film and Best Original Screenplay. —Wedemeyer

32. Crazy Rich Asians

For some reason, I waited longer than most to watch Crazy Rich Asians. I refused to buy into the hype. Now though, I get upset if I don’t manage to watch the movie at least once a month. Funny how the tides change! Based on the bestselling novel by Kevin Kwan, Crazy Rich Asians delivers on every aspect of the title. The predominantly Asian and Asian American cast capably showcases the cultural differences between the two groups, and it’s easy to just get lost in the romance between Nick and Rachel. At this point it’s absolutely wild to me that we don’t have a sequel yet! —Givens

Warner Bros.

31. The Big Sick

There are, in every genre, tentpole moments; times when a movie or a person or an idea lands with such measured gravity and brilliance that you know, from there going forward, everything is going to be different. With rom-coms, there have been five undeniable tentpole moments. There was Diane Keaton powering Annie Hall to four Oscar wins in 1977. There was Nora Ephron basically wholesale inventing the modern rom-com with When Harry Met Sally in 1989. There was Boomerang showing what it would look like if everyone but white people weren’t boxed out. There was Julia Roberts putting up untouchable numbers in the ’90s with Pretty Woman, My Best Friend’s Wedding, Notting Hill, and Runaway Bride. And then there was The Big Sick revitalizing and modernizing the rom-com again in 2017. Driven to brilliance by Kumail Nanjiani, Zoe Kazan, Holly Hunter, and Ray Romano (not to mention Emily V. Gordon, who cowrote the movie), it’s a smart, tender, nuanced movie that completely upends the things audiences had come to expect from rom-coms while simultaneously serving us exactly what we needed from the genre. —Shea Serrano

30. 27 Dresses

Katherine Heigl, queen of the mediocre rom-com. James Marsden, king of the guys who never get the girl. Smash them together and you get 27 Dresses, an underrated highlight of both their rollercoaster rom-com careers. For once, Marsden isn’t the forlorn, overlooked ex. (For that, refer to The Notebook, Enchanted, or really any of his other roles.) Our guy locks it down this time, and it’s what he deserves as the charming, cheeky journalist writing a story about Heigl’s character, who is quite literally always the bridesmaid, never the bride. The movie is admittedly uneven, but highlights include rom-com classics like a bar sing-along scene and an elite outfits montage of the titular 27 dresses. —Halliwell


29. Working Girl

Classifying Working Girl as only a romantic comedy kind of undersells the movie’s significance. From the opening aerial shots of the Statue of Liberty and administrative assistant Tess McGill’s (Melanie Griffith) commute into Manhattan on the Staten Island Ferry, it’s clear that director Mike Nichols is going to be tackling big themes—the American Dream, sexism in the workplace, the cruelty of the corporate ladder, classism. Yet, in addition to all that, there’s a goosebump-inducing love story between Tess and Harrison Ford’s Jack Trainer. The two team up and fall in love. Their final scene together may be one of the most iconic in rom-com history; they eat breakfast as Tess gets ready to head off to the first day of her new job. Before she leaves, Jack sends her off with a brand-new monogrammed lunchbox, complete with a peanut butter and jelly sandwich. It’s the best gift a partner can give. —Siegel

28. There’s Something About Mary

First of all: I think if Green Book never comes out, then this movie is sitting comfortably in the top 20 on this list. Peter Farrelly should’ve been satisfied with hair gel that isn’t actually hair gel being his legacy.

There’s Something About Mary was a revelation—a deliriously R-rated rom-com that made $370 million worldwide on a $23 million budget, launched Ben Stiller and Cameron Diaz into the stratosphere, and became the only film to ever envision what it might look like if a man got his frank and beans caught in a zipper. This movie broke real ground by adding debauchery and madness to a traditionally buttoned-up genre, a stroke of genius topped only by casting peak ’90s Brett Favre as Mary’s longtime ex-boyfriend. —Gruttadaro

Twentieth Century Fox

27. Can’t Buy Me Love

Can’t Buy Me Love belongs to a group of of-their-time rom-com classics with movies like Secret Admirer and Just One of the Guys—those ’80s films with the sort of premises and scripts that might elicit that well-known response of “They could never make this today.” But of those movies, Can’t Buy Me Love stands at the top. Starring an incredibly young Patrick Dempsey and a quintessential ’80s teen movie love interest in Amanda Peterson, it’s a pioneering play on the “Give Geeks a Chance” trope: Ronald is a dork who loves expensive telescopes but dreams of being cool; Cindy is the popular girl who throws bangers and spills wine on her mom’s suede. Their relationship begins as a business transaction and culminates with the realization that it’s so much more than that, with a lot of teen drama in between. Put it this way: The movie’s so good that Nick Cannon and Christina Milian had no choice but to remake it for the 2000s crowd. —Gruttadaro

26. Boomerang

You have Eddie Murphy, one of the funniest and most charming people to have ever walked across a Hollywood stage, playing an unstoppably suave bachelor intent on sexing his way toward finding what he deems to be a perfect woman. You have Robin Givens opposite him, playing said “perfect woman,” who, rather than falling for any of Murphy’s tricks and tactics, twists him up into a knot over and over again. You have David Alan Grier and Martin Lawrence playing Eddie’s friends, neither of whom has any real idea how exactly to process what exactly it is that makes women fall for Eddie but both of whom approach the conundrum in hilarious ways. You have Halle Berry as the unexpected “regular woman” (lol) Eddie eventually ends up with. You have John Witherspoon giving maybe the greatest ever walk-off home run scene in rom-com history. And you have Grace Jones, Eartha Kitt, Tisha Campbell, a young Chris Rock, and Geoffrey Holder chucking joke grenades into every scene they’re in. And still, despite being arguably the funniest collection of people ever assembled in a rom-com, Boomerang is able to squeeze the emotion out of you whenever it decides to do that. —Serrano

25. Say Anything

Say Anything does not live by boom box alone. Yes, its signature image is among the most recognizable movie moments ever, encapsulating the concept of rom-coms in a single frame. But Cameron Crowe’s directorial debut is much more than that indelible scene. Lloyd Dobler is the patron saint of people who take time to decide on a direction in life, and his unlikely but credible bond with Diane Court captures the dream of being able to “go out with someone you wouldn’t even have to go out with.” The film unfailingly respects its characters and its audience; as Roger Ebert wrote, “That such intelligence could be contained in a movie that is simultaneously so funny and so entertaining is some kind of a miracle.” I’m not normally a proponent of reboots or decades-distant sequels, but I wonder what Lloyd and Diane are up to now. It’s probably better to leave their love in the past than to learn that Diane didn’t ride the Reid fellowship to fame and fortune and Lloyd ended up buying or selling something processed after all. But it’s a testament to the OTP of ’80s teen movies that neither I nor Crowe can quit them.—Lindbergh

24. Love Actually

Love Actually is many things to many people: rom-com, Christmas movie, ensemble cast production, Liam Neeson-biting-off-an-awful-lot-to-help-his-kid genre film. To some, it is a problematic mess in which unresolved plot details and bad behavior (infidelity, flirting with subordinates, traveling to Milwaukee) paints a shallow picture of love while celebrating the nebulous connection between romance and the holidays. And yet, to me, it is perfect, or at least endlessly charming in its cheesy portrayal of love in many forms. —Princiotti

23. Moonstruck

There’s no city more romantic than New York (sorry, Paris), and there’s no New York movie more romantic than Moonstruck (sorry, Manhattan). Nicolas Cage—just 23 at the time—would go on to make a career out of his irrepressible eccentricity, but in Moonstruck, every single actor is vibrating on his gloriously weird frequency, giving indelible, odd life to John Patrick Shanley’s Oscar-winning screenplay. As Brooklyn widow Loretta Castorini, Cher matches Cage beat for beat in his portrayal of maimed baker Ronny Cammareri, the estranged younger brother of her sad-sack fiancé Johnny. In Shanley’s indelible words, she’s a bride without a head; he’s a wolf without a foot. Once he flips a table out of rage and lust, it’s all over for them.

This is a story where the two lovers’ first date takes place at the Metropolitan Opera, where they watch the starving artists of La Bohéme succumb to tuberculosis. In a world where the cold, hard ground awaits us all, what choice do we have but to love who we can and hold family close? As Ronny says, we’re here to ruin ourselves and break our hearts and love the wrong people and die. Might as well get on with it. —Alison Herman

Metro-Goldwyn-Mayer

22. My Big Fat Greek Wedding

Before it would become the highest-grossing romantic comedy of all time, My Big Fat Greek Wedding began as a one-woman play by Nia Vardalos that was broadly based on her own personal life and her big, rowdy family. The story of how it got from A to B involved Rita Wilson and Tom Hanks—and also Vardalos’s insistence that studios retain the extreme specifics of her vision. The result is a 2002 film that is goofy yet precise, a rom-com brimming with vim and a LOT of fam. (Vardalos wrote on Reddit that her own dad used Windex on a wart, that “the woman is the neck” is something her mother said, and that Toula isn’t just the lead character in the movie—it’s her cousin’s name.) A feast of bundt cake and lamb, frosted-cupcake wedding dresses and lunch bag moussaka, My Big Fat Greek Wedding is a movie with a satisfying conclusion: that it’s all Greek to everyone, and that really, we’re all just fruit. —Baker

21. The 40-Year-Old Virgin

Not everything Judd Apatow touches these days turns to gold—see The Bubble or that tweet about how Will Smith’s slap could’ve killed Chris Rock—but you have to hand it to the man for, among many other accomplishments, somehow perceiving while producing Anchorman that the person playing Brick Tamland was capable of being a romantic lead. Apatow and Steve Carell cowrote this movie based on one of Carell’s recurring improv sketches; crucially, their script and Carell’s tender portrayal (coupled with the commitment to do his own stunt in the chest-wax scene) made Andy a sympathetic protagonist whose plight was relatable, rather than the pitiful butt of every joke. Whether or not you think The 40-Year-Old Virgin is one of the best rom-coms ever, you must admit it was one of the most influential. The movie made a star out of everyone associated with it who wasn’t one already, and it established a lucrative lane for many bro-y-but-still-sensitive rom-coms to come. —Lindbergh

20. High Fidelity

The top five things that are great about High Fidelity:

5. Nick Hornby, author of the book that inspired the film, essentially laid the groundwork for 70 percent of digital media. Say what you want, but lists are entertaining and useful.

4. It goes without saying, but the soundtrack of this movie is, as the protagonist Rob would say, “an all-timer.” The Velvet Underground. The Kinks. Elvis Costello. Stevie Wonder. A collection of artists genuinely worthy of musical snobbery.

3. This is the film that introduced mainstream audiences to Jack Black, and without Jack Black, we would have never seen School of Rock.

2. Speaking of the cast, we can’t slight John Cusack here. Say Anything is another rom-com classic, but High Fidelity is arguably Cusack’s finest work in any genre. A perfect balance of humorous pretension and relatable vulnerability; it’s hard to imagine another actor embodying this role so well.

1. High Fidelity wasn’t afraid to get dark; it ranked breakups and songs about death, and it took care to acknowledge its central relationship was made up of two deeply flawed people. This movie might not be the first that comes to mind when you think of “romantic comedy,” but High Fidelity is one of the most authentic depictions of a relationship you’ll see on film. —Jenkins

19. The Princess Bride

I don’t always agree with Aaron Rodgers, but I can still recall when he named The Princess Bride as his favorite film, choosing it over movies you’d assume a football player would list like The Dark Knight. But what was great about Rodgers’s seemingly subversive choice was that it really wasn’t all that shocking. The Princess Bride defies our expectations of both fantasy and romance with its use of comedy and creative storytelling, masterfully tied together by screenwriter William Goldman. Once more, we root for all the memorable characters, from our main love interests Princess Buttercup and Westley to the beloved sidekicks Inigo Montoya and Fezzik and the unnamed grandfather and grandson who help facilitate the tale. It’s a classic rom-com—even football players know it. —Wedemeyer

Twentieth Century Fox

18. Bridget Jones’s Diary

Plenty of entries on this list are adaptations of age-old stories in the public domain, from Shakespeare’s comedies to Austen’s social farce. But Bridget Jones’s Diary is a kind of dual translation—not just of Pride & Prejudice, though Colin Firth does provide a visual link in his second turn as (a version of) Mr. Darcy. It’s also based on Helen Fielding’s hit novel of the same name, the high-water mark of the so-called “chick lit” wave. Renée Zellweger may do a shockingly good British accent for an American star, but it’s Fielding who deserves credit for filtering Elizabeth Bennet’s headstrong heroine through a more modern set of neuroses like drinking, weight gain, and modern careerism. As a result, Bridget Jones’s Diary is a contradictory mix of timeless themes and details that mark it as a relic of, or perhaps a fun throwback to, the early aughts. Anyone can relate to Bridget’s struggle to choose between Mr. Right and Mr. Wrong, especially when her Mr. Wrong is played by Hugh “Gosh” Grant; her use of Spanx in the getting-ready montage, on the other hand, is a bit more specific to its moment. Bridget Jones is eternal, but also a time capsule—a pretty neat encapsulation of the romantic comedy itself. —Herman

17. Two Weeks Notice

Hugh Grant portrays the selfish and helpless real estate billionaire George Wade; Sandra Bullock is Lucy Kelson, an environmental lawyer who agrees to work for George’s firm only after she realizes she can save one of her beloved community centers. Lucy grows frustrated with her boss’s baby behavior, but after she decides to resign, George and Lucy spend her final two weeks at work falling for each other. What makes this movie memorable is Bullock’s steadfast commitment to physical comedy. Not only does she hug a wrecking ball (you’re welcome for the inspiration, Miley), her head is savagely hit by a tennis ball, and she slides in the middle of a wet highway on her way to relieve herself after eating too many chili dogs. Being that this was one of the first productions to take place in New York City after 9/11, this film also serves as yet another love letter to the Big Apple. Yes, I know When Harry Met Sally features Katz’s Deli and the Met, but Two Weeks Notice has Norah Jones, Mike Piazza, and Donald Trump as supporting characters. This movie also had us all running to LimeWire to rip Counting Crows and Vanessa Carlton’s version of “Big Yellow Taxi.” If that isn’t an endorsement, I don’t know what is. —Bridget Geerlings

16. The Holiday

One time I was venting about a guy to my friend, and after listening politely for a few minutes, she cut in to say “Watch The Holiday,” like she was a doctor writing a prescription. Reader, I soon understood why. The 2006 film centers around two women who are romantic opposites: Iris (Kate Winslet), who’s spent years in Surrey, England, pining for an unavailable ex, and Amanda (Cameron Diaz) who drives away her partner by burying herself in her L.A.-based movie-marketing business. The two of them meet on a house-swap website and agree to trade lives for the holidays—a move that allows for gratuitous real estate montages and, most crucially, opportunities to find love where they’d least expect it. These adventures add up to a hopeful take on heartbreak: that beyond each dead-end relationship is a world of possibility for what comes next. It’s a message so soothingly executed by Nancy Meyers that it really does kinda feel like medicine. —Bereznak

15. Hitch

A film with prime Will Smith, Kevin James, and Eva Mendes; a fun and engaging story; and a baller soundtrack? Not only is Hitch one of the most underrated rom-coms of all time, I am a firm believer that it is Will Smith’s best performance as an actor, PERIOD. He’s good in Ali, sure; Oscar-worthy in King Richard; he doesn’t get enough love for his voice work in Shark Tale. But let’s really talk about it! This scene right here IS cinema. “They don’t need no pizza, they got food there” as James does his “white boy at the disco” bit is one of the funniest moments in rom-com history. It’s time to finally give Hitch it’s just due.

Next subject. —Jomi Adeniran

Columbia Pictures

14. Four Weddings and a Funeral

Four Weddings and a Funeral isn’t a great comedy because it’s peppered with comedians ripping off one gag after another. (You know who puts me in a mood to laugh? Kristin Scott Thomas.) It’s a great comedy because it explores the joy of friendship; when you’re with your friends, the laughs just come naturally—but a great group of friends gets you only so far, as Hugh Grant’s Charlie discovers when he falls for an elusive American who keeps popping up in his life. Even though the film bounces from one farce to another over the course of its four weddings, the most memorable scene is the funeral, in which John Hannah’s Matthew recites W.H. Auden’s “Funeral Blues” at the memorial service for his recently deceased partner. It’s dramatic relief, so to speak, a solemn reminder that love and friendship are about tears as well as laughter. —Michael Baumann

13. Groundhog Day

If Bill Murray’s original hopes for Groundhog Day won out, the film may not have made this list: “It was an interpretation of the myth about how we all repeat our lives because we’re afraid of change,” he said of his initial thoughts on the original script. “I thought it could just be the funniest thing ever.” But director Harold Ramis had a different vision: “the idea that true love can save you from a life of monotony,” Murray said. So while on the surface, the granddaddy of time-loop movies doesn’t appear to be a pure rom-com—the romance element doesn’t become a factor until the film’s second half—it expresses a sentiment core to human nature. Murray plays the coarse Phil Connors, who finds himself repeating the same day over and over again. After learning to live within the surreality of the situation, he begins to focus on self-improvement: skating, ice sculpting, learning French, just becoming a decent human overall. Eventually, it helps him get the girl and in turn, escape the hell he’d been living through (for possibly as long as 34 years). Plenty of rom-coms have focused on the inadequate man having to grow to find the love he needs. Few have made it an existential question to the degree Groundhog Day did. —Sayles

12. While You Were Sleeping

Lucy (Sandra Bullock) is a transit worker who counts tokens (not the non-fungible ones) for Chicago subway riders. All she wants in life is to be seen and to get at least one stamp on her damn passport. She also has an unrequited crush on Sandy Cohen—I mean, Peter Callaghan, who is played by Peter Gallagher. Peter is an affluent commuter who almost gets run over by the actual subway before Lucy spots him and saves his life. While escorting him to the hospital, she is mistaken for his fiancée and fails to correct this misinformation as Peter’s family rushes to his bedside as he suffers from a coma. Lucy, who would otherwise be home alone for the holidays, is swept away by the kindness bestowed on her by Peter’s family. After agreeing to spend Christmas with them, she meets Peter’s brother Jack (denim advocate Bill Pullman). As Peter and his iconic eyebrows rest away on a hospital bed, Lucy shockingly begins to fall for Jack. Come for Pullman and Bullock, which is electric enough to power all of the film’s Christmas trees, and stay for Michael Rispoli workshopping a character for The Sopranos. More importantly, I feel compelled to add that this is Daniel Radcliffe’s favorite Sandra Bullock film. —Geerlings

11. Something’s Gotta Give

The only thing better than a Nancy Meyers kitchen is a Nancy Meyers kitchen in the Hamptons inhabited by Diane Keaton and Jack Nicholson making pancakes, just on the brink of realizing they’re falling in love. There’s something about adding love interests in their golden years to the “enemies to lovers” trope that just makes it hit different. Erica and Harry are sharp, aware, and quicker to realize their attraction to one another because they’ve both already lived rich, full lives. I mean, we’re already cutting off turtlenecks before the movie is halfway done! Plus, Something’s Gotta Give is full of whopper lines: “Words have been invented to describe women like you,” and, “You are a woman to love.” And yet even as Harry says these things—and literally goes to the hospital on three separate occasions in direct response to Erica—he struggles to realize that Erica has already changed the trajectory of the rest of his life. But after a beard and a little repentance to the young women of Manhattan, he gets there. And just as every rom-com should, it all ends in Paris, sealed with a kiss. —Walker

Columbia Pictures

10. Forgetting Sarah Marshall

Forgetting Sarah Marshall should’ve aged poorly, considering the plot is a sort of Garden State-by-way-of-sophomoric Apatovian silliness. But it didn’t, because it’s one of the funniest movies ever made. There are comedies—good comedies, funny comedies—whose best joke isn’t as side-splittingly hilarious as Paul Rudd’s deadpan delivery of, “Oh yeah, you’re that guy who works with Kaiser Permanente.”

It’s the kind of movie that’s funny on repeat viewing specifically because there are jokes you missed the first time through because you were laughing so hard. There’s no wasted effort from its loaded cast, from Jonah Hill to Mila Kunis to Russell Brand, at that magical moment in time when only one side of the Atlantic was sick of Russell Brand. And amid all the R-rated comedy is a surprisingly endearing hero: a cuddly, self-loathing, piano-playing giant played by Jason Segel. To change or remove one joke, one weird side character, would be to diminish this masterpiece. —Baumann

9. The Wedding Singer

Adam Sandler has made a lot of rom-coms. Some of them are bad. Some are fine. Some are just obvious excuses for, like, a free trip to Hawaii. But The Wedding Singer is none of these—The Wedding Singer is perfect. It’s patient zero for Sandler and Drew Barrymore’s chemistry, which is so undeniable that they’ve run it back multiple times in the years since. It’s one of the best collections of ’80s music ever assembled, with contributions from David Bowie, the Smiths, the Psychedelic Furs, Spandau Ballet, the Cure, Thompson Twins, and so many more. And most importantly, it is, line for line, one of the funniest rom-coms ever made—from Sandler’s sad wedding singer performance to Steve Buscemi’s best man speech to Jon Lovitz’s “and I’m reaping all the benefits” line reading to this interaction, which I think about at least once a week. It’s a movie you can watch 1,000 times and still wanna watch in full when it’s playing on TBS—I know because I’m currently describing my usual Saturday night. —Gruttadaro

8. My Best Friend’s Wedding

It’s a simple recipe. First you take the greatest rom-com star to have ever lived (Julia Roberts). Then you add in one of the all-time-great plot setups (a woman’s best friend is getting married, which nudges her toward the conclusion that her best friend should be getting married to her instead). Then you add two spotlight-bright performances from people the camera can’t get enough of (Cameron Diaz and Rupert Everett). Then you add a handsome and clueless man whose only job is to be handsome and clueless (Dermot Mulroney). Then you add a scene that all but demands you scream “JUST TELL HIM THAT YOU LOVE HIM RIGHT NOW BEFORE IT’S TOO LATE!” (the part when Julia Roberts and Dermot Mulroney are on the boat together). And then, finally, a little sprinkle of magic (the part when Rupert Everett is making up a story about how his pretend relationship with Julia Roberts started and ends up with breaking out into song at a lunch). And that’s how you get one of the best, most fun, smartest, most enjoyable rom-coms to have ever been put to film. —Serrano

7. Sleepless in Seattle

Sleepless in Seattle’s genius is distilled in one of its simplest scenes: A bathrobe-clad Annie Reed (Meg Ryan) settles into her pink kitchen, using a knife to remove the skin from an apple in one continuous band as she listens to talk radio. The camera closes in on her face as the voice of widower Sam Baldwin (Tom Hanks) describes the magic of meeting his late wife, and she begins to weep. In Annie’s face is a deep longing, the restlessness of someone who wants more than Mr. Perfectly Fine but feels absolutely ridiculous for it. Meanwhile, 2,764 miles across the country, Sam comforts his son by offering a single detail to remember his mom by: “She could peel an apple in one long curly strip,” he tells him. “The whole apple.”

Little coincidental glimmers like these tether Annie and Sam for most of Nora Ephron’s perfect 1993 rom-com, as the two of them live out their own pretty OK relationships while longing for that fabled and elusive spark. It’s only in the 11th hour, after many plane rides and several leaps of faith, that they find it in each other atop the Empire State Building. Witty banter, a stacked cast, and dreamy scenery aside, this is one of those rare, hopeful stories that makes heroes out of romantics, suggesting no obstacle is too great for even the slimmest chance at the real thing. —Bereznak

TriStar Pictures

6. Notting Hill

Julia Roberts may be our finest meta movie star. Even before the Ocean’s Twelve stunt, she was a girl, standing in front of a boy, asking him to love her—except that girl happened to be an actress named Anna Scott, with a level of fame not unlike Roberts’s nearly a decade past her breakout in Pretty Woman. Roberts is a great actor, but she’s an even better movie star. Notting Hill may be her greatest star performance, because she doesn’t have to try to pretend she’s an ordinary citizen.

She’s also given a perfect scene partner in Hugh Grant, who’s pulling off the opposite trick. Notting Hill leaves Roberts free to embrace her natural charisma; as stammering bookstore owner William, Grant perfects the underdog persona that somehow makes you forget you’re watching one of the most handsome and charming humans alive. Notting Hill is a perfect snapshot of two performers at the top of their respective games, assisted by screenwriter Richard Curtis on a legendary run of quotable scripts. Before Rose Matafeo’s delightful Starstruck came along, Notting Hill set the bar. —Herman

5. Jerry Maguire

By the late ’90s, incessant quoting of Jerry Maguire’s most memorable lines—e.g., “Show me the money!,” “You complete me,” and “You had me at hello”—turned writer-director Cameron Crowe’s film into a corny joke. But make no mistake: It’s one of the best rom-coms of the decade. Over the course of two hours, the titular rogue sports agent shakes his maniacal workaholism and becomes vulnerable. Tom Cruise, who was nominated for an Academy Award for his performance, manages to make the transformation believable. But he couldn’t have done it without Renée Zellweger, who plays his only employee/single mom Dorothy Boyd with infinite sweetness. Zellweger deserved an Oscar nomination, too. She got robbed. —Siegel

4. Clueless

Two permits do not equal a license, but inspired casting, some of the best one-liners in cinematic history, and a boatload of yellow plaid equals a genre-defining ‘90s teen movie. Amy Heckerling’s adaptation of Jane Austen’s Emma via Beverly Hills is more com than rom, but its climax takes place when the ditzy but deep Cher Horowitz realizes that she is “totally butt crazy in love with Josh,” her ex-step-brother, played by a young Paul Rudd. Before this moment, Cher and Josh argue constantly over her outward frivolity, yet she constantly gets the better of him verbally. “If I ever saw you do one thing that wasn’t 90 percent selfish, I’d die of shock,” he tells her at one point, to which Cher responds, “Oh, that’d be reason enough for me.” This is the joy of Clueless—it mocks what it loves and it loves what it mocks. Also, there’s never been a better on-screen diss than “You’re a virgin who can’t drive.” —Princiotti

3. You’ve Got Mail

The third film featuring beloved actors Meg Ryan and Tom Hanks together, and the second that also involved the late director Nora Ephron, You’ve Got Mail is at once a well-worn rom-com story line and a project that could really only have been released in 1998. In the movie, Ryan plays Kathleen Kelly, the owner of a children’s bookstore called The Shop Around the Corner—one of several references to a 1940 Jimmy Stewart film with a similar plot in which IRL enemies become enamored pen pals without realizing. But in You’ve Got Mail, that plot is given an upgrade for the times involving an over-30 chat room on dial-up AOL; a cutthroat book superstore reminiscent of late-’90s rising behemoths like Borders or Barnes & Noble; and characters who don’t yet carry cellphones and instead write overwrought emails about bouquets of freshly sharpened pencils that recipients are legitimately exhilarated to receive.

In a Vanity Fair oral history, supporting actor Heather Burns admitted that the film’s premise had kind of nagged at her a little: “I was young and really idealistic, and I got a little mad that she ends up with the guy who’s putting her out of business,” Burns said. (Also, Joe Fox? Kind of a dick!) But Ephron saw it differently. “Heather, the older you get,” she told her, “you’re gonna realize that things change and there’s not very much that you can do about it. And the city changes, and that’s just the way it is.” These days You’ve Got Mail isn’t just dated, it’s practically obsolete: those big bad mega-booksellers of the world have been all but eliminated by the bigger, badder Amazon; the New York Observer that Greg Kinnear’s character wrote for was destroyed by Jared Kushner. And yet that spark between Hanks and Ryan? As reliable and invigorating as those glorious changes of season in New York City, no matter how many times they come back around. —Baker

2. Pretty Woman

Without Julia Roberts, Pretty Woman isn’t second on this list. Without Julia Roberts, Pretty Woman probably isn’t even on this list. The premise of Pretty Woman is sticky, and there’s a lot more messiness to the conceit, to the plot, to the Jason Alexander of it all to contend with than your average meet-cute. The romance, and especially the comedy of this movie, lives and dies on the charisma of its heroine. And in 1990, no one was more charismatic than a fresh-out-of-the-gate Roberts singing Prince in the bathtub. Sure, some folks had discovered her in Mystic Pizza, but for most, Roberts was a revelation in Pretty Woman. That’s not to discredit Richard Gere, who excels here at being as steely as he is handsome, but if we were ranking iconic rom-com moments, Julia Roberts cackling at having a necklace box snapped on her fingers has to be number two, second only to… well, no spoilers for the rest of this ranking. Pretty Woman changed the rom-com game for well over a decade, and its legacy continues to reverberate throughout art and culture. Pretty Woman-ing has become a verb, an entire trope in its own right, and the inspiration for an annual date on The Bachelor. It’s practically an eponym for the entire genre. You looking for a rom-com, sugar? You got one. —Walker

1. When Harry Met Sally

When Harry Met Sally is the greatest rom-com ever made. It’s the product of the galacticos of the cute, talky, adult comedy: Nora Ephron, Rob Reiner, Meg Ryan, Billy Crystal, and Carrie Fisher, all at the peak of their powers. It’s set in the perfect place and at the perfect time: a bourgeois corner of New York City in the 1980s, when men wore sweaters and women wore hats. You couldn’t ask for better building blocks.

But that’s not what makes it great. A majority of romantic comedies set their focus on the beginning of a relationship: the exciting part. The thesis of When Harry Met Sally is that love is not about the spark, but about how you feel years down the line. And somehow, over the course of just 95 minutes, we get to see a relationship develop over the course of 12 years. Even considering that there are basically only four characters in the movie, it’s an astonishing bit of writing and acting to establish two leads who just get each other so completely. It’s the rom-com every filmmaker should aspire to make, and the romance every couple should aspire to have. —Baumann

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