The Best Rom-Coms of All Time, from ‘Some Like It Hot’ to ‘Roxanne’

82. “Crazy Rich Asians” (Jon M. Chu, 2018)

The broad strokes of Kevin Kwan’s bestselling, compulsively readable “Crazy Rich Asians” trilogy are familiar enough: it’s a girl meets boy story — and a girl-meets-boy’s-deranged-family story — the kind of subject matter that’s always ripe for a rom-com. But Kwan’s books, loosely based on his own coming-of-age in Singapore, take that classic narrative and turn it into a vivacious love letter to contemporary Asian culture, populated by unique characters and set in the eye-popping locales of one of the world’s richest countries.

Jon M. Chu’s big screen adaptation of the material, a groundbreaking studio film that is entirely populated by Asian-American performers (the first of its kind since “The Joy Luck Club,” more than 25 years ago), is a loving take on Kwan’s books, bundled up in a wildly entertaining package. —KE 

81. “Bros” (Nicholas Stoller, 2022)

After 120 years, give or take, Hollywood finally has a mainstream queer rom-com answer to films like Nora Ephron’s “You’ve Got Mail” and “Sleepless in Seattle.” Hell, it’s taken just as long to make a mainstream LGBTQ movie that isn’t about pain and suffering or trauma or systemic homophobia. Enter screenwriter/star Billy Eichner and director Nicholas Stoller’s “Bros,” a snarky, fitfully raunchy meet-cute for the age of Grindr (or here, a dating app cheekily called Zellweger).

The actual breaking of ground is that the cast is top-to-toe gay, gay, gay… and that’s pretty much where it stops. The screenplay’s contours are broadly conventional, but that’s a good thing. When we talk about wanting to be seen, a lot of us really mean that what we want is a gay version of our ’90s rom-coms when the genre was at its best. “Bros” fits the bill. —RL 

80. “Scott Pilgrim vs. The World” (Edgar Wright, 2010)

It’s been over a decade since Edgar Wright plugged audiences into the referential matrix that is “Scott Pilgrim vs. the World,” a comic-inspired, combat-heavy romance with an incisive wit and some of the best video game representation in movie history. In the film based on Bryan Lee O’Malley’s graphic novels of the same name, Michael Cera leads as narcissistic twenty-something Scott. Caught between Mary Elizabeth Winstead’s self-possessed Ramona and Ellen Wong’s lovestruck schoolgirl character Knives, Scott embarks on a journey toward love and self-respect that sees him battle seven (really, eight) “evil exes” (Chris Evans! Mae Whitman! Jason Schwartzman!) and his own worst impulses. Kieran Culkin, Anna Kendrick, Aubrey Plaza, and more round out a ridiculously great cast we’re still, to quote Scott, “in lesbians” with. —AF

79. “(500) Days of Summer” (Marc Webb, 2009)

Joseph Gordon-Levitt falls for karaoke-singing, IKEA-shopping, record store–browsing Zooey Deschanel in this love letter to the quirky side of the Los Angeles dating scene. To which we demand, “Where does that exist??!” Answer: Nowhere, because “(500) Days of Summer” is a projected fantasy that inevitably ends with the cold harshness of winter. —SB

78. “Shithouse” (Cooper Raiff, 2020)

Written, directed, and co-edited by its reluctant 22-year-old star with some help from his friends, “Cha Cha Real Smooth” Sundance breakout Sundance Raiff’s vulnerable DIY gem tells a coming-of-age story about a mopey college freshman who’s struggling with the whiplash of leaving home. He meets a girl, they spend a magical night together, things get awkward in the morning but maybe they’ll still be able to help each other figure shit out… you know how it goes. It’s basically the Platonic ideal of the movie you’d expect from a suburban white American softboy who’s been raised on Richard Linklater and “Sex Education.” —DE

77. “Two for the Road” (Stanley Donen, 1967)

Audrey Hepburn and Albert Finney journey through a surprisingly sad road trip comedy in Stanley Donen’s “Two for the Road.” The 1967 rom-dramedy charts a couple’s declining marriage across a decade of road trips through the south of France. Caught somewhere between “Scenes from a Marriage” and Lucille Ball and Desi Arnaz’s “The Long, Long Trailer,” Frederic Raphael’s nimble script won him the Academy Award for Best Original Screenplay. —AF

76. “Trouble in Paradise” (Ernst Lubitsch, 1932)

Renowned as a cinematic sophisticate with a knack for conjuring romantic charm, Ernst Lubitsch championed clever, subtle storytelling across his more than 30-year career. “The Shop Around the Corner” is his masterwork (ranking number 8 on our list), but “Trouble in Paradise” was a landmark achievement for establishing the fabled “Lubitsch touch.” The 1932 romantic comedy stars Miriam Hopkins and Herbert Marshall as lover criminals who cross paths with a perfume tycoon, played by Kay Francis. A witty love triangle soon emerges against the sparkly backdrop of post-Années folles Paris. —AF

75. “Eagle vs Shark” (Taika Waititi, 2007)

Before he broke into the mainstream with “Thor: Ragnarok,” Taika Waititi charmed his New Zealand brethren (and plenty of film festival audiences and indie cinephiles alike) with his particular brand of off-kilter comedy. Waititi has, thankfully, not lost that creative spark as he’s moved into bigger projects, and even a look back at his feature directorial debut reveals that his humor and point of view have long been fully formed.

Or, put another way: did you know that Taika Waititi’s first film was a rom-com, and that it’s very Taika? It’s true! Starring his frequent cohort Jemaine Clement and an absolutely charming Loren Horsley (who developed her character Lily before the film was even written), “Eagle vs Shark” is the kind of “misfits in love” story that only Waititi could make. Lily and Clement’s Jarrod might not seem like prime picks for a big love story, but as they gently (and amusingly) get to know each other in fits and starts, a true romance blossoms. —KE

74. “Long Shot” (Jonathan Levine, 2019)

Before second gentleman Doug Emhoff, there was first mister Fred Flarsky — both of them Jewish, but only one of them real. Don’t feel sorry for the fictional one, though, as Fred’s hilarious journey from Vice-like gonzo journalist to America’s most powerful beta male is the stuff of one of the most under-appreciated rom-coms in recent years. Seth Rogen adds a new edge to his usual charming schlub routine as a Vice-like gonzo journalist who writes himself out of a job before a brief encounter with his former babysitter, current Secretary of State, and potential future POTUS (Charlize Theron as Charlotte Field) leads Fred down a new career path as a political speechwriter. 

“Long Shot” doesn’t exactly reinvent the wheel as Fred and Charlotte fly around the world and bond over “Game of Thrones” spoilers, but the movie has a lot of fun pushing its “will they/won’t they?” mechanics into “would she/how could she?” territory, the chemistry between its leads is sweet enough to make a certain kind of sense, and director Jonathan Levine keeps the world around them so well-balanced that the story is able to absorb a rocket-based assassination attempt, a leaked masturbation video, and even the shocking reveal that someone is a Republican without overwhelming its characters. If “Long Shot” settles for a degree of bipartisanship it doesn’t seem to believe in, this sharp but cuddly rom-com will still go down as one of the only studio movies about the Trump-era political ecosystem that managed to find love in a hopeless place. —DE

73. “Shall We Dance?” (Suo Masayuki, 1996)

No wonder this became an international sensation destined for a Hollywood remake. The personalities in Suo Masayuki’s delicate character study are so vividly drawn and conveyed through posture, gestures, and eye-lines that even a non-Japanese speaker could understand the film without any subtitles (but please leave them on, because this script is written with a jeweler’s precision).

Yakusho Koji plays a Tokyo salaryman whose life is defined by his job: “I sold my soul to the firm,” he says, because he bought a house in the suburbs to provide a better life for his wife and daughter. He’s a drone, a desk jockey caught up in life that he’s forgotten to live — and his marriage is suffering for it. 

A splash of color sashays into his world when he glimpses a ballroom dance studio on the train home and finds himself drawn to it. Of course, his interest has something to do with Mai (Takenaka Naoto), one of the dance instructors. But his attraction to her becomes something deeper: As he takes lesson after lesson, his physical self is reawakened – stirred up from the depths of his sedentary office existence. Through his attraction to Mai, our man actually reignites his marriage. 

Suo, who also wrote the script, nails the counterintuitive notion that getting closer to someone else can involve doing something solely for yourself. This is serious stuff, to be sure, but it’s also incredibly funny, as Shohei finds ballroom dancing has a pretty steep learning curve (and that one of his co-workers is already a secret hoofer). “Shall We Dance?” also resonates on the deepest levels, and its climactic sequence — in which the hero appears to blow off the big final “Strictly Ballroom” competition in favor of stewing alone in a pachinko parlor — is genuinely suspenseful. Its American remake, starring Richard Gere and Jennifer Lopez, isn’t quite as urgent, but remains delightful in its own right. —CB

72. “Keeping the Faith” (Edward Norton, 2000)

Jessie is a friend, yeah I know he’s been a good friend of mine… If those words don’t immediately conjure the image of Ken Leung in a karaoke shop with a fake Korean accent, have you even lived? The greatest of Edward Norton’s directing work stars the actor in a rare comedic role as a Catholic priest in a love triangle with his Rabbi best friend, played by none other than Ben Stiller at the start of his blockbuster comedy peak. “Meet the Parents” would come out later that year, swiftly followed by “Zoolander” and “The Royal Tenenbaums,” but it’s Stiller’s performance as hot single Rabbi Jake Schram that cemented him as leading man material for a very specific subset (oy — Jewish!) of cinephiles. If the Norton/Stiller duo seemed an odd couple in 2000, Hollywood’s quirky girl du jour Jenna Elfman provided the perfect wild card energy. Her charismatic turn as their shared object of affection made the comedic chemistry sizzle between these three unusual suspects. 

The premise is simple: Two best friends take wildly different turns in life — one’s a priest (Norton), and one’s a Rabbi (Stiller). When the girl that got away in middle school suddenly reappears in their lives as a vivacious breath of fresh air, they both fall for her despite having many reasons not to. For Jake, both his mother and his congregation wouldn’t have him marry a shiksa; Brian’s reasons are more obvious. As Jake and Anna begin an affair, they must keep it secret from Brian, causing much confusion and opportunities for slapstick. Though we’re ultimately rooting for the people who are actually allowed to have sex, each relationship feels evenly balanced and rooted in something real, which is not an easy task in a love triangle. Add to that an enviable supporting cast that includes Anne Bancroft as a pitch-perfect Jewish mother, Eli Wallach as a rabbi, and the venerable Milos Forman in a rare acting role, and “Keeping the Faith” is divine enough to restore your faith in rom-coms. —JD

71. “She’s All That” (Robert Iscove, 1999)

“Am I a bet? Am I a bet? Am I a fucking bet?!” It’s the line that launched a thousand imitators, showed off the power of a single well-placed “fuck” in an otherwise PG-13 movie, inspired the masterpiece known as “Not Another Teen Movie,” and was also penned by no less than M. Night Shyamalan. That’s a lot of film history packed into just a few choice words. Robert Iscove’s 1999 high school-set romantic comedy “She’s All That” may host some of the most instantly out-of-date elements of any other film on this list — the slang title, a subplot involving Matthew Lillard appearing on “The Real World,” and a dance sequence led by Usher himself — but the classic DNA that drives the film keeps it feeling vital.

You already know the “Pygmalion”-sized shape of it all: Rachael Leigh Cook is the school dork (she sports a ponytail! she wears glasses!!), Freddie Prinze Jr. is big man on campus Zack, and the late Paul Walker is his shit-stirring best pal who bets him he can’t make over Cook’s Laney Boggs into a member of their popular clique. Zack’s plan works a little too well, and as he changes the art-loving Laney into something more palatable to their image-obsessed cohorts, she ends up having an even bigger impact on him, pushing Zack to become more true to himself. (Special bonus: he also starts digging her entire wacky family, including her baby brother, played by a pre-pre-pre-“Succession” Kieran Culkin.)

Of course, it all blows up spectacularly once Laney discovers that their entire relationship was built on a bet — pardon, a fucking bet — a heartbreaker of a sequence that exemplifies why Cook’s flinty charm is a such a good fit for the material. A happy ending for all (well, all who deserve it including, apparently, Usher) is assured, but the film takes some interesting twists to get there, all of which make its finale feel all the more satisfying. —KE

70. “Last Days of Disco” (Whit Stillman, 1998)

Whit Stillman’s warm and witty brand of Austenian aristocratic comedies are sorely missed today, and, if anything, their very ‘90s-centered mores make for a fascinating time capsule of that moment. The best of the bunch is “Last Days of Disco,” starring Chloe Sevigny and Kate Beckinsale as two recent grads working as junior associates at a publishing house (how romantic that was even a career aspiration at one point?). They’re looking for love and sex in the last days of disco, at the start of the 1980s, and have to swat away plenty of Stillmanian assholes, like Chris Eigeman as a drug-addicted club manager who pretends to be gay to dump women guiltlessly. But there is a sweet love story at the movie’s core, with Sevigny’s drifting Alice forging a connection with a district attorney (Matt Keeslar). A final fantasy sequence of the pair dancing to “Love Train” on a packed subway is a fade-out for the ages. —RL

69. “The Glass Bottom Boat” (Frank Tashlin, 1966)

In Frank Tashlin’s wonderful spy rom-com “The Glass Bottom Boat,” Doris Day shines as Jennifer Nelson: a warm Catalina Island native who, when she’s not hanging out with her many pets or working in aerospace PR, spends her time performing as a “mermaid” for her family’s local tourist attraction. When Jennifer is accidentally hooked by fisherman/engineer Bruce Templeton — an all-time charming Rod Taylor — the duo’s awkward encounter spirals into a Cold War-era misunderstanding featuring a super glitzy disguise and a plate of high-tech hors d’oeuvres you’ll never forget. —AF

68. “The Palm Beach Story” (Preston Sturges, 1942)

Though “The Lady Eve” reigns supreme as the best Preston Sturges rom-com — and ranks even higher on this list — “The Palm Beach Story” is worth revisiting for its unbridled commitment to goofiness and tongue-in-cheek approach to the restless nature of love. Five years into her marriage with little financial security, Gerry Jeffers (Claudette Colbert) leaves her husband Tom (Joe McCrea) for Florida in an effort to find a better life for them both. —AF

67. “Lover Come Back” (Delbert Mann, 1961)

Screenwriters Stanley Shapiro and Paul Henning shared a nomination for (what was then known as) the Academy Award for Best Story or Screenplay thanks to the delightful comedy of errors that is “Lover Come Back.” Not to be confused with the 1946 Lucille Ball film of the same name, this Doris Day and Rock Hudson outing — the dazzling duo enjoyed three movies together, including “Send Me No Flowers” and the masterful “Pillow Talk” — tells the tale of two advertising executives, previously rivals, brought together by a case of mistaken identity and a marketing scheme gone sideways. —AF

66. “Masculin Féminin” (Jean-Luc Godard, 1966)

Pioneer of the French New Wave movement, Jean-Luc Godard is remembered for films that were at once innovative and provocative — practically daring mid-century audiences to not be dazzled by material they’d otherwise find objectionable. 1966’s “Masculin Féminin” is no exception, positioning leads Jean-Pierre Léaud and Chantal Goya as orbiting lovers in a tragicomic landscape that examines politics, sex, and, yes, romance through a playfully painful drama about twenty-somethings living in Paris. —AF

65. “I Know Where I’m Going” (Michael Powell and Emeric Pressburger, 1945)

The title “I Know Where I’m Going!” only hints at the smarts hidden in Michael Powell and Emeric Pressburger’s extraordinarily clever snapshot of marital cold feet. Wendy Hiller leads as Joan Webster: a self-assured woman who finds herself unexpectedly delayed en route to her wedding to an older man. Trapped by a storm, she suddenly finds herself falling for a mysterious man (played by Roger Livesey) and questioning her suddenly uncertain future. —AF

64. “The Princess Bride” (Rob Reiner, 1987)

Adapted by William Goldman from his beloved fantasy book of the same name, “The Princess Bride” is sacred ground in the American comedy landscape. Rob Reiner’s snappily paced 1987 classic tells the story of Buttercup (Robin Wright) and Westley (Cary Elwes), a young maiden betrothed to the horrible Prince Humperdinck (Chris Sarandon) and the man who will stop at nothing to save his true love. Toss in three hapless kidnappers — Inigo Montoya (Mandy Patinkin), Fezzik (André the Giant), and Vizzini (an “inconceivable!” Wallace Shawn) — and you’ve got all the players needed for one of cinema’s greatest fairytales. —AF

63. “My Sassy Girl” (Kwak Jae-yong, 2001)

Kwak Jae-yong’s massively popular “My Sassy Girl” was, at the time of its 2001 release, one of the five highest-grossing films in the country’s history. And there’s a good reason for that! No, it’s not the truly risible direct-to-DVD American remake starring Jesse Bradford/Elisa Cuthbert that you probably didn’t even know existed until this very moment. It has more to do with the fact that this epic three-part love cranks every aspect of its genre to the nth degree, somehow building a coherent (and ultimately irresistible) story from a zillion competing tropes. 

It starts with an engineering student named Gyeon-woo (Cha Tae-hyun) and the suicidal — and borderline sadistic — manic pixie dream girl (a spirited Jun Ji-hyun) he meets along the train tracks one night. If she first presents as more of a tainted fantasy than an actual human being, this screwball adventure leans into the girl’s heightened nature as hard as it can, sending her and Gyeon-woo through a multi-year adventure that involves everything from a hostage crisis to squash, a time capsule, and the most emotionally significant tree this side of “In the Mood for Love.”

It’s all a bit much by American standards, but that muchness works in its favor until the very end; perhaps Hollywood could stand to give us a little bit more. —DE

62. “2 Days in Paris” (Julie Delpy, 2007)

“2 Days in Paris” plays out like a sustained panic attack in real time. French-born photographer and ailment-addled Marion (Delpy) and her hypochondriac, chain-smoking boyfriend Jack (Adam Goldberg) are on a lovely holiday across Europe that culminates in them heading to Paris to meet her parents for the first time. It turns out, Paris is also home to many, many of Marion’s ex-boyfriends, and it becomes a too-tall order for the jealous Jack as circumstances foam way beyond a head, and Marion is seized by faux panic attacks over men she clearly still pines for — even if it’s just for validation. This is definitely a “nervous romance” of the “Annie Hall” ilk, but Delpy and Goldberg’s volatile chemistry as they continually flip the script on each other makes for a car-crash love story always lurching from the swooning to the prickly and discomfiting. —RL

61. “The Worst Person in the World” (Joachim Trier, 2022)

For any millennial who ever pratfell in the face of their own indecision-making, Joachim Trier’s “The Worst Person in the World” holds up a grimacing double-sided mirror that flips between a hard-to-stomach, piercing reality check, and a warm, inviting embrace of relatability for the very same reason. Renate Reinsve gives a full-stop stunning breakout performance (one that won her the Best Actress prize at Cannes) as Julie, a tormented approaching-30-something who waffles between busted professional aspirations and ineffectual lovers, with ultimately no one to come home to at the end of the day but herself. —RL

60. “Modern Times” (Charlie Chaplin, 1936)

One of the few movies where Chaplin “gets the girl,” “Modern Times” is the point where the silent master began leaving behind his Little Tramp. In fact, it’s worth asking if he’s even the Little Tramp at all in this movie. He starts “Modern Times” fully employed as a factory worker, so maybe not (though he finds himself sacked in short order). Halfway into the film, he meets Ellen, “The Gamin” (Paulette Goddard). She’s a beggar arrested for stealing to feed her siblings — her introductory shot is a close-up with a knife between her teeth — and the Tramp tries to tell the police he’s the real thief. How’s that for a meet-cute? 

The Tramp actually wants to go to jail because he’s guaranteed a square meal there, but he can’t shake the Gamin, and they end up looking out for each other and having a little fun too: They go roller-skating in a department store after-hours when the Tramp gets a job there as a night watchmen, set up house together in a waterfront shack, and she even gets him a job as a waiter at a café where she’s performing. Chaplin’s camera could not be more in love with Goddard’s face, and their feelings for each other swell to the tune of his iconic “Smile.”

The genius of “Modern Times,” like most of Chaplin’s near-perfect filmography, is his ability to mix different emotions together into an ecstatic rush of pure feeling. “The Gold Rush” might have the happiest ending of any Chaplin film — the Tramp’s now a millionaire and gets the girl — but “Modern Times” resolves in a more complicated place: Yes, the Tramp and the Gamin are together, but they’re both unemployed and find themselves on an empty road facing an uncertain future. At least they’re facing it arm in arm. —CB

59. “Something Wild” (Jonathan Demme, 1986)

“Something Wild” was the exact shot of adrenaline Hollywood desperately needed at a time when its ability to create anything adult and fun was running on empty. Jonathan Demme brought the screwball comedy into the ‘80s, as the prototypical yuppie (Jeff Daniels) is “kidnapped” by the free-spirited Lulu (Melanie Griffith) and taken on a wild, sexy, adventure that turns his uptight world upside-down.

Fueled by one of the most adept and effective pop music soundtracks ever assembled, we too are ready to let our hair down and follow the impulsive Lulu wherever she takes us. 

And then… well, to quote Demme super fan Paul Thomas Anderson: “Enjoy that first hour — because when it turns, it’s gonna turn. And it’s gonna be really exciting when it does.” OK, so the dark turn isn’t necessarily “romantic” (Ray Liotta’s appearance brings pure menace), as the film expertly plays on your rom-com expectations. And yet this isn’t some intellectual play on genre, or some “look-at-me” directorial exercise; nor is there even a pinch of moralizing  about how these characters got in this situation. Instead there’s a characteristically deep sense of humanity that unifies Demme’s film, which at its heart is a road movie about the thrill of stepping outside yourself and what you open yourself up to when you do. —CO

58. “Palm Springs” (Max Barbakow, 2020)

There have been so many riffs on the “Groundhog Day” formula that it can sometimes feel like the movies themselves are stuck in an endless time loop, but Max Barbakow’s witty and wise “Palm Springs” was the first iteration of the old formula alters the fundamental nature of the whole equation. What if — the movie wonders — instead of relegating one person to a cyclical purgatory that they’re forced to repeat over and over until they learn the error of their ways, you relegated two people to the same pocket of the Twilight Zone? The mind boggles at the implications! Imagine spending the rest of your meaningless existence with the same person. Imagine being stuck in a perpetually static purgatory where meaningful change can only be seen through the eyes of the sad bastard suffering alongside you. Imagine being surrounded by a million strangers in a world of limitless possibilities, and winding up with the same one every night because of one fateful choice that seemed like a good idea a million years ago. Imagine… being married.

The overarching plot of “Palm Springs” isn’t especially novel, but each scene is just sweet, funny, and demented enough to feel like a little surprise. Andy Samberg is a nihilistic delight as a guy who’s trapped at a desert wedding for a short eternity, and Cristin Milioti is a winsome force of comic violence as the new girl who wanders into his forever cycle. Together, they combine for a smart and breezy summer watch that explores the ins and outs of what it truly means to share forever with someone, resulting in an unadulterated slice of pro-marriage propaganda at a time when so many people are opting for the single life. —DE

57. “To All the Boys I’ve Loved Before” (Susan Johnson, 2018)

Lara Jean Covey (Lana Condor) has a problem with her crushes: she hides them. Lara Jean buries her emotions deep, deep down, refusing to get too close to anyone — especially cute boys she likes — beyond the close confines of her family. Then, when that becomes too much to bear, she lets loose by penning love letters to her dearest crushes (when the film opens, they number five), which she hides away in her closet. So what happens when those letters are let out into the world? Chaos!

Netflix’s breakthrough rom-com cuts through a lot of noise to get at the simple truth that has powered its genre since long before the movies were even invented: Find a sweet protagonist, and even the most outlandish of storylines can work. Yes, Lara Jean’s situation is bizarre (why did she address the letters!?), but Condor’s performance brings Lara Jean to life with wit and sweetness. It also helps that director Susan Johnson is a good fit for the material, and her ability to pull together quick-cut flashbacks and inventive ways to make chatty monologues work keeps the film ticking along whenever it threatens to fizz out. Mostly, though, “To All the Boys” keeps a tight grip on the formula of every rom-com and adapts it for the younger set. Every beat of the film might be obvious, but that doesn’t detract from the enjoyability of watching an indelible young heroine like Lara Jean figure out her own life and just maybe fall in love in the process, and both of the lesser sequels that Netflix rushed out have only underlined what makes the original so good. —KE

56. “Knocked Up” (Judd Apatow, 2007)

Judd Apatow flirted with the rom-com formula in “The 40 Year Old Virgin,” but it wasn’t until “Knocked Up” that he went all in on the genre, reluctantly dragging the genre into the 21st century by capitalizing on the happy accidents of hookup culture. Apatow’s script hinges on the oldest of dynamics: A battle of the sexes between a man and woman from opposite social circles. Here, Ben Stone (Seth Rogen in his first starring role) is a total burnout who spends his days trying to invent Mr. Skin with his stoner housemates, and Alison Scott (Katherine Heigl) is a high-powered E! correspondent who’s just been promoted to on-air talent.

The war between them is locked into a stalemate from the moment it starts, as Alison gets pregnant from their one-night stand and decides that she wants to keep the baby, effectively binding she and Ben together for life. 

Back in the day — before the word “shmshmortion” would even be mentioned in a movie like this — it was often a man’s values that saved a woman from herself, but “Knocked Up” flips the script and tilts the playing field in the other direction while still giving audiences plenty of time to laugh at the stunted hilarity of Rogen, Jonah Hill, Jason Segel, Jay Baruchel, and Martin Starr all living together in a massive puff of their own pot smoke. The result is a rom-com that feels traditional and progressive in equal measure, and also happens to offer the movies’ most honest template for the experience that any two people might have during a pregnancy. —ZS

55. “Roxanne” (Fred Schepisi, 1987)

Steve Martin brings plenty of nose and even more heart to Fred Schepisi’s 1987 take on “Cyrano de Bergerac.” Daryl Hannah plays the titular Roxanne: an astronomy student who becomes the shared love interest of a town when she decides to stargaze there for the summer. When Martin’s brilliantly funny firefighter chief CD befriends Roxanne, he blames his unusually large nose for their unrequited love. Enter Chris, played by Rick Rossovich: a hunky meathead unable to keep up with Roxanne until he gets the help of — you guessed it. From Martin’s unforgettable insult monologue (“Excuse me, is that your nose or did a bus park on your face?”) to the slapstick stunts around Roxanne’s cabin, this one’s a genuine treasure too sweet to forget a-snout. —AF

54. “What’s Up, Doc?” (Peter Bogdanovich, 1972)

Barbara Streisand peppers Peter Bogdanovich’s “What’s Up, Doc?” with equal parts chaos and charm. The fast-talking 1972 screwball delight centers on a baggage mix-up: comedically chaining Streisand’s zany Judy Maxwell to three people with her same suitcase — including Ryan O’Neal’s love interest Howard Bannister — at a San Francisco hotel. With top-secret documents and lavish jewels involved, Judy’s natural propensity for whacky antics lands her and Howard in a heap of trouble. Of course, “Love means never having to say you’re sorry.” —AF

53. “Some Like It Hot” (Billy Wilder, 1959)

Billy Wilder penned the screenplay for “Some Like It Hot” with I. A. L. Diamond after collaborating with Marilyn Monroe on “The Seven Year Itch” in 1955. Monroe stars as ukulele player Sugar Kane, who unknowingly crosses paths with two men (Tony Curtis and Jack Lemmon) who are running from a Chicago mobster, in what is easily her best rom-com, if not her outright best film. Disguised as women, the pair of musicians join an all-ladies band headed for Miami, unleashing an ensemble comedy for the ages in the process. Curtis and Monroe enjoy an unforgettable (and just so darn likable!) attraction that’s made all the more fun by the film’s giddy final act. —AF

52. “The Awful Truth” (Leo McCarey, 1937)

The soon-to-be-divorced Jerry and Lucy Warriner should not be together. But in “The Awful Truth,” stars Cary Grant and Irene Dunne help director Leo McCarey make the case that sometimes, no matter how undesirable, the love we feel is unavoidable. Each unhappy and suspecting the other of infidelity, the Warriners begin the 1937 screwball requesting a divorce from the courts. They’re told their marriage will be permanently dissolved in three months… But can the would-be divorcées stay away from each other long enough to let that happen? —AF

51. “Ruby Sparks” (Jonathan Dayton & Valerie Faris, 2012)

It took six years for Jonathan Dayton and Valerie Faris to follow-up “Little Miss Sunshine,” and it’s a shame “Ruby Sparks” didn’t quite reach the same level of popularity and reverence. Written by lead actress Zoe Kazan, “Ruby Sparks” tells the story of a young author (Paul Dano) who falls in love with a character from his new novel after she appears to him in real life.

Kazan channels her inner Charlie Kaufman with the script but substitutes Kaufman’s weighty existential dread for a more accessible charm, bolstered by the lovable and authentic chemistry between her and her real-life love Dano. Kazan — writing herself a role that she plays to increasingly virtuosic perfection — uses the fantasy element of her script to pose intelligent questions about love, to interrogate the premise of the manic pixie dream girl, and to dissect the many different roles that partners can play for one another in a relationship.

Few of the films on this list are as sincerely engaged in thinking about the mechanics of romance, and even fewer are able to do so with as much heart and honesty as “Ruby Sparks.” —ZS

50. “Don’t Go Breaking My Heart” (Johnnie To & Wai Ka-Fai, 2011)

Johnnie To can basically do anything. Hardcore gangster dramas (“Election”)? No problem. Transcendent action movies (“Vengeance”)? Why not. A feather-light caper about Hong Kong pickpockets that’s told with the precision of a Rolex watch (“Sparrow”)? You should be embarrassed for asking. With that in mind, it should hardly come as a surprise that To and his frequent co-director Wai Ka-Fai are also masters of the romantic comedy, and nowhere is that more evident than in 2011’s “Don’t Go Breaking My Heart.”

The film stars Gao Yuanyuan as a beautiful analyst named Chi-yan who just so happens to be newly single after discovering that her boyfriend is having a baby with another woman. That’s great news for Sean (Louis Koo), the brash and handsome CEO whose office window provides him a front-row seat into the story of Chi-yan’s life. But the plot thickens (in a way that might feel too contrived in any other genre) when our heroine is reacquainted with a sweet-natured alcoholic who needs the attention of a pretty girl to put him back on his feet and rediscover his genius as an architect. 

And so we have the equation for a bizarre love triangle that doesn’t hinge on wealth so much as what the heart wants, as Chi-yan is forced to choose between flashy charm and a calmer form of devotion. This being a Johnnie To movie, however, the economy is always a specter of some kind, and the global recession arrives just in time to elevate a smooth rom-com into a richer story about the ways in which love and money tend to be curiously intertwined. The strained plot mechanics only help to strengthen To’s antic visuals (and vice-versa), and the brutal 2014 sequel only serves to emphasize all the subtle things that “Don’t Go Breaking My Heart” gets right. —DE

49. “13 Going on 30” (Gary Winick, 2004)

One of the last early aughts rom-coms to use a classic construction — it’s basically a gender-swapped “Big” that manages to avoid the sticky questions of that Tom Hanks-starring classic — to tell a fairy tale-like story, Gary Winick’s feature follows an awkward teen who, thanks to the power of wishes and also glitter, transforms into the kind of glamorous adult she can’t imagine ever growing into.

Jennifer Garner’s wide-eyed innocence is a perfect fit for Jenna Rink, who instantaneously goes from dorky kid to high-powered adult, and discovers that getting what you wish for isn’t all it’s cracked up to be. The film folds in lots of fun touches, from Judy Greer in the best friend role (with secrets!) to a large-scale dance sequence set to “Thriller,” but it really excels when Jenna goes after her childhood bestie Matt (Mark Ruffalo), who needs to be convinced that she’s still the girl he loved when they were just kids. —KE

48. “Bend it Like Beckham” (Gurinder Chadha, 2002)

A global smash that continues to resonate around the world, Gurinder Chadha’s “Bend it Like Beckham” tells the story of Jesminder (“Jess” Bhamra, an 18-year-old football obsessive in Hounslow, London) whose Sikh parents won’t let her play the game she loves. Jess loves her parents and respects where they’re coming from, but the heart wants what the heart wants, and it isn’t long before she covertly begins playing for a local team (a charming Keira Knightley helps pressure her into it, not that Jess needs much of a push to spend her days gawking at the smoldering coach played by Jonathan Rhys Meyers).

From there, Chadha’s film weaves a tender, slow-burn romance into Jess’ journey towards self-actualization, as she attempts to please her traditional parents while forging her own identity. A laugh-out-loud comedy with sports on its mind and its heart on its sleeve, “Bend it Like Beckham” embraces the pluralistic nature of being a British Punjabi Sikh all while maintaining a loose spirit that keeps it firmly in the feel-good realm. —JD

47. “Obvious Child” (Gillian Robespierre, 2014)

Like any coherent genre, rom-coms happily embrace formula, but that doesn’t mean said formula can’t get serious freshening up and some clever twists. That’s why Gillian Robespierre’s Sundance 2014 hit, featuring an utterly charming Jenny Slate in her first major lead role, works so well: it knows the history it springs from, and then it happily makes it over in its own image. 

The set up is initially recognizable: Slate stars as struggling standup Donna (an occupation that adds a necessary dose of amusing vulgarity to the whole thing), who gets dumped by her lame boyfriend and promptly falls into a one night stand with the sweet Max (Jake Lacy). Various problems and pratfalls keep the duo from really making a go of this whole relationship thing, but their chemistry and growing affection for each other keeps them pushing ahead until they are ready to take the next step.

The twist is a major one, unthinkable in a previous era: Donna gets pregnant after their one night stand and wants an abortion (even before it debuted in Park City, “Obvious Child” was known as an “abortion comedy,” but it’s much more than that). It’s funny and fresh and sad and open and honest, and it’s also proof of just how many possibilities the genre can contain. Robespierre and her leading lady never play the film’s concept for cheap laughs or petty drama, instead packaging a winsome character study of Donna inside a sweet romance with Max, who recognizes her humanity and honesty and does his damndest to honor them. What could possibly be more romantic than that? —KE

46. “Belle Epoque” (Fernando Trueba, 1992)

A picaresque romantic comedy that feels like it got pleasantly lost somewhere between “Teorema” and Almodóvar, Fernando Trueba’s Oscar-winning “Belle Epoque” finds love in the days before the Spanish Civil War as it follows a young deserter who shacks up with an old artist in the countryside and seduces at least three of the man’s four comely daughters.

A boisterous film that’s buoyed by the grim (but endless) possibilities of life during wartime, “Belle Epoque” unfolds with the bawdiness of “The Decameron,” as Trueba careens from camp to melodrama in pursuit of true love. Even with its patriarchal attitudes and narrow ideas of female sexuality — the landowner’s daughter each represent a different kind of feminine charm — “Belle Epoque” holds up. Some of that can be explained away by the beauty of the film’s setting, the specificity of its time, and the Buñuelian snarl of its humor.

The rest is owed to a young actress by the name of Penelope Cruz, who plays the artist’s innocent fourth daughter with so much star power that her performance continues to shine a couple of decades later. —DE

45. “High Fidelity” (Stephen Frears, 2000)

John Cusack is an iconic sad sack in director Stephen Frears’ adaptation of Nick Hornby’s novel, “High Fidelity,” about an unlucky-in-love music geek who obsessively sifts through the ruins of his many failed relationships — including, most recently, with Laura (Iben Hjejle), who’s fed up with Rob’s (Cusack) stubborn refusal to grow up.

The women drifting in and out of Rob’s life, from Catherine Zeta-Jones to Lili Taylor, illuminate Rob’s best and worst qualities, and why they’ve damned him to eternal singledom. “High Fidelity” certainly takes the prize for best soundtrack of any romantic comedy, packed with glorious all-timers from The Kinks, The Velvet Underground, Bob Dylan, Elvis Costello, and more. —RL

44. “Breakfast at Tiffany’s” (Blake Edwards, 1961)

Even with “Days of Wine and Roses,” “Victor/Victoria,” and dozens more titles to his name, filmmaker Blake Edwards never escaped the slinky shadow of “Breakfast at Tiffany’s.” The image of Audrey Hepburn in a black Givenchy dress — tiara atop her head, cigarette holder in her mouth, Cat (yes, capital “C”) draped about her shoulders — is one so clichéd it almost immediately induces visions of clearance bins selling tattered “Scarface” posters. But bother to put the well-celebrated classic on and there’s no denying its timeless appeal, from leading man George Peppard and the perfect rainy kiss to Hepburn’s melancholic performance of “Moon River,” which won Best Original Song at 34th Academy Awards. —AF

43. “Go Fish” (Rose Troche & Guinevere Turner, 1994)

Inspired by the success of Todd Haynes’ “Poison” and frustrated by lesbian films that looked nothing like their actual lesbian lives, Rose Troche and Guinevere Turner decided to take matters into their own hands by shooting a tiny little indie called “Go Fish” in 1994.

Filmed in black and white in Chicago for an estimated $15,000, “Go Fish” went on to make roughly $2.4 million, proving that LGBTQ indies could make a profit. Turner played Max, a headstrong writer who begins dating the older, quieter Ely (V.S. Brodie), despite initial reservations. Max’s friends — a jovial lesbian peanut gallery — offer unsolicited advice and plenty of laughs.

No one dies, and no one comes out; a novelty for gay films at the time. Charming, vital, and honest in ways that Hollywood struggles to be, “Go Fish” changed the game for queer cinema and pushed all of indie filmmaking towards a more inclusive future. -JD

42. “The Big Sick” (Michael Showalter, 2017)

You couldn’t make up this sharp and winsome true story about the harrowing romance that blossomed between (now) husband-and-wife Kumail Nanjiani (“Silicon Valley”) and writer Emily Gordon, a courtship that began with a culture clash and then threw in a little coma, as a treat.Gordon and Nanjiani wrote the script together as an intense form of couples therapy, only for uber-producer Judd Apatow and director Michael Showalter to recognize its potential and help shape it into Sundance gold. The action starts when a Chicago girl named Emily (played with radiant warmth by Zoe Kazan) falls in love with a Pakistani-American comic who moonlights as an Uber driver (Nanjiani plays himself to inimitable effect). But his family’s traditional values soon trouble the waters, and the lovebirds’ first big fight lingers in the air for a short eternity when Emily falls prey to a mysterious illness. Her parents (Holly Hunter and Ray Romano, both magnificent) don’t know what to make of their daughter’s ex as he gloomily hangs by her bedside, but they learn to appreciate his tortured affections before their sleeping beauty comes back to life.Not only does “The Big Sick” forge one of the wittiest and most winsome couples in recent rom-com history, it also hilariously contrasts two very different sets of parents in a way that manages to bridge the gap between tradition and pluralism without disrespecting anyone’s worldview. Gordon and Nanjiani received a well-deserved Best Original Screenplay nomination for synthesizing their own story into something this funny and beautiful, proving that talented people can still mine plenty of relevance from the old rom-com formula. —AT

41. “Kissing Jessica Stein” (Charles Herman-Wurmfeld, 2001)

Too often thought of as Jon Hamm’s former partner, Jennifer Westfeldt is also the plucky writer and star of this indie romantic comedy about a neurotic Jew who, like a bisexual Woody Allen, just can’t make up her mind. Westfeldt plays the titular Jessica, who comes across a pre-Craigslist personal ad so perfectly written it leaves her speechless (a rarity for her).

When the person on the other end turns out to be a woman named Helen (played by co-writer Heather Jeurgenson), Jessica embarks on the slowest-moving lesbian affair in history. The movie is entertaining as can be from start to finish, but its uptight heroine struggles to reconcile her evolving sexual identity with her mother’s decidedly static expectations.

It’s the kind of New York romance that rarely gets made anymore: There are charming montages set to Ella Fitzgerald’s version of “Manhattan,” a scene-stealing best friend (Jackie Hoffman), and a lovably overbearing Jewish mom (Tovah Feldshuh) who gets in the way without ever becoming a villain — in fact, the scene where she finally comes around is one of the sweetest moments of its kind. It’s true that “Kissing Jessica Stein” sometimes feels like it’s struggling against the overwhelming heteronormativity of its genre, and there are valid reasons to wish that it were just a bit gayer. But the film is a lot like its protagonist: so damn lovely that everyone wants to kiss it. —JD

40. “My Best Friend’s Wedding” (P. J. Hogan, 1997)

What do you get when you add up a jealous best friend, a rushed wedding, and a bubbly, naïve bride? Well, that would be the iconic “My Best Friend’s Wedding,” which tested whether Julia Roberts really is eternally America’s sweetheart even if she’s playing an antagonist, by way of food critic Julianne. Arguably a subverted take on the rom-com, “My Best Friend’s Wedding” uses Roberts’ natural charisma to root for someone that we know, logically, we shouldn’t. Does she deserve to end up with childhood pal Michael (Dermot Mulroney) and break up what seems to be a happy soon-to-be marriage? Not quite. But yet Roberts still has us holding our breath while she announces that she’s the one for our leading man. And yet…she’s not. While Mulroney picks his blushing bride Kimmy, played by Cameron Diaz, we see what cynical Julianne despises. “My Best Friend’s Wedding” isn’t your feel-good rom-com, but it sure does fit as a Valentine’s Day classic. —SB

39. “Emma” (Autumn de Wilde, 2020)

While some audiences might have balked at the promise of a new “Emma” when the Gwyneth Paltrow-starring ‘90s dramedy still looms so large (not to mention Amy Heckerling’s brilliant modern riff, “Clueless”), first-time filmmaker Autumn de Wilde’s sumptuous adaptation on the material soon allayed any concerns. Starring Anya Taylor-Joy as the eponymous heroine, the film is a mostly faithful take on the classic story of a delightful heiress who dabbles in matchmaking, resulting in both wonderful and just awful pairings.

Livened up with de Wilde’s keen eye (she’s best known for her photography and music video directing, so she knows style) and a sharp script from Man Booker Prize-winning author Eleanor Catton, the film is more biting, sexy, and funny than most other Austen adaptations, and — thanks to the fidgety and explosive chemistry between Taylor-Joy and Johnny Flynn’s rumpled Mr. Knightley — it feels more human and alive than almost any other Regency-era period piece.  De Wilde’s flashy background might have initially recommended her for the material (the costumes have never been better, the country houses have never been this divine), but her desire to turn long-recognizable characters into brand-new versions is perhaps her greatest skill as a filmmaker. Her “Emma” is a three-tiered wedding cake of a romantic comedy, but it’s warm and satisfying in a way that reheated leftovers almost never are. —KE

38. “Think Like a Man” (Tim Story, 2012)

Based on Steve Harvey’s best-selling comedic advice book, “Act Like a Lady, Think Like a Man,” this winning rom-com presents audiences with multiple intertwining stories of coupledom that serve as examples in support of the various theories endorsed by the source material — imagine a good, black version of “He’s Just Not that Into You” and you’ll be on the right track. The result is a heartfelt and cohesive mosaic that ties together the best stand-alone strands of Harvey’s book. 

Rather than use Harvey’s treatise as a foundation, screenwriters Keith Marryman (good name) and David A. Newman use it as a starting point for creating characters that are likeable and leap off the screen. More comfortable in its own skin than some other mainstream black comedies of its time, and carried by a star-studded cast that includes Kevin Hart, Regina Hall, Gabrielle Union, Meagan Good, and even Steve Harvey as himself, “Think Like a Man” is charming enough to transcend its sketchy promotional origins and comes together into a multi-dimensional look at modern love that’s actually fun to watch. —TO

37. “Sleeping With Other People” (Leslye Headland, 2015)

Leslye Headland’s raucous feature debut, “Bachelorette,” made it clear that the playwright and filmmaker (she adapted her own play for the film) wasn’t at all interested in sickly-sweet movies about nice people doing nice things. The ladies of “Bachelorette” are bad, but the honesty that Headland mined from them marked her as a clear-eyed creator to watch. Her follow-up feature, “Sleeping With Other People,” didn’t back down on the truth-telling, but it also folded in a pair of characters well worth rooting for, flaws and all.

Jake (Jason Sudeikis) and Lainey (Alison Brie) first meet as horny co-eds, and when they’re reunited years later, that hasn’t changed, though it’s taken on a darker cast: they’re sex addicts, and both of them have ruined nearly every relationship they’ve been in because of their shared illness. Their crazy chemistry doesn’t help matters as the pair attempts to be just friends, but it’s sexy as hell to watch on-screen — “Sleeping With Other People” is easily one of the most seductive rom-coms in recent memory — and it’s touching to watch the two of them try to better themselves, with Jake working towards a healthy relationship as Lainey tries to cut ties with the toxic Matt (Adam Scott, going whole-hog on playing the asshole).

Plenty of romantic comedies have found pleasure and pain in watching their leads untangling their predictably messy lives as they are similarly shoring up their burgeoning relationships, but Headland’s film flips the script and places the premium on Jake and Lainey as individual people. Their issues and troubles aren’t just vessels for their romantic journey, but for true self-actualization. The great trick of “Sleeping With Other People,” however, is that this clever twist only makes the film a lot funnier and more alive than so much of its genre brethren. If nothing else, it’s the only film on this list that makes a cheeky self-pleasuring lesson involving a juice bottle embody all its best qualities: hilarious, sweet, and hotter than it has any right to be. —KE

36. “Punch-Drunk Love” (Paul Thomas Anderson, 2002)

A frantic quasi-musical about violently isolated people who learn that they don’t have to condemn themselves to their sadness, Paul Thomas Anderson’s fourth feature distills an epic’s worth of emotion and bottles it up in a cheap blue suit. Adam Sandler was revelatory as Barry Egan, the low-brow comedian repurposing his signature rage into something new just by denying it a place to go. He can’t just win a golf tournament and or retake second grade; he’s got a business to run, a thousand sisters to handle, and a hole in his heart the size of Hawaii. And then there’s Lena Leonard (Emily Watson), who looks at Barry and sees a harmony, her desire setting off a love story where the senses blur together like the whole film has been touched by synesthesia.

“Punch-Drunk Love” is a tiny movie, but Robert Elswit’s camera roves around Barry’s factory with a manic curiosity that borders on Chaplin-esque, resulting in the first PTA film that doesn’t feel like it’s carving out a story so much as building one from the ground up. That spirit of creation is infused into the characters, who discover that opportunity abounds in this world (in pudding and people alike), and that they have the power to get on a plane and chase love down before it gets away. Love is out there, you just have to pick up the phone.

If you’re lucky, you might find Lena Leonard in her hotel room. And if you’re really lucky, you might get patched through to Philip Seymour Hoffman, whose heavenly appearance galvanizes this strange concoction with a bunch of spittle and an arsenal of f-bombs. If this isn’t the greatest scene ever committed to celluloid, it’s damn close to it. —DE

35. “Love Actually” (Richard Curtis, 2003)

We know. This is pretty much the most potentially off-putting Christmas rom-com ever made. And yet, there’s a reason why Richard Curtis’ unapologetic orgy of tired genre tropes has been seriously debated by more people than universal healthcare — why any comprehensive overview of these movies has to reckon with it in one way or another. Like a demented supercut of the most ridiculous parts from every previous rom-com, “Love Actually” may not be one of the greatest films of its kind (mileage tends to vary!), but it’s also inarguably all of them, wrapped in tinsel and weaponized into a nuclear bomb of artificial cheer. 

On a beat-by-beat basis, it feels like it was written by a neural network that was forced to binge-watch the other 49 movies on this list. Each scene violates the basic protocols of human behavior in its own special way: Andrew Lincoln going full “Peeping Tom” on his best friend’s bride. Alan Rickman’s sadistically hornt secretary talking about “dark corners for doing dark deeds.” Laura Linney’s entire wardrobe. There isn’t a single moment that reads as realistic. Not Colin Firth’s meet-cute with his Portuguese housekeeper, and not the bit where Prime Minister Hugh Grant dances through 10 Downing Street, not the part when the President of the United States sexually harrasses a random woman the second they’re alone together (okay, maybe that one checks out). 

Cut together, however — and carried along by the exhaltant genius of Craig Armstrong’s score — these psychotic details combine into something far greater than the sum of their parts. They swirl inside the warped glass of Curtis’ snow globe to create an enchanted space where love defies all logic, and even life-ruining lust can seem magical in a certain light. It’s a film so high on its own supply that it doesn’t seem to recognize that all of the subplots about established relationships are riddled with tragedy, or that opening a frothy British rom-com with an earnest 9/11 reference might not set the right tone. This is a nearly fatal mega-dose of what movies like it do best, and one way or another, it proves that love is the only universal form of agony that we can all laugh at together. —DE

34. “Something’s Gotta Give” (Nancy Meyers, 2003)

Nancy Meyers prompted a kind of Keatonaissance with 2003’s irresistible golden years romance “Something’s Gotta Give.” The movie was Diane Keaton’s biggest box-office success in nearly a decade, restoring one of the genre’s all-time queens to the top of her game, and reminding moviegoers of the comedic gifts she first displayed in the (considerably more complicated) movies of Woody Allen. She earned a well-deserved Oscar nomination for her turn as happily single playwright Erica Barry, first wooed by Keanu Reeves’ dreamboat of a doctor, then by Jack Nicholson as a moneyed Lothario with a taste for younger women — namely her own daughter, played by Amanda Peet.

Keaton and Nicholson’s chemistry both in and out of the bedroom begs the question of why these two icons had never co-starred in a romantic comedy before (“Reds” doesn’t quite fit the bill). While Meyers’ Hamptons-set kitchen porn is on full display here, the emotions are grounded and real, often bruising but always funny. A post-breakup montage of Erica screaming for an entire day is absolutely peak Keaton, and the ending is still worth arguing about more than a decade later. —RL

33. “Harold and Maude” (Hal Ashby, 1971)

So good that you can’t even stay mad at all of the twee indies it went on to inspire, Hal Ashby’s iconically morbid classic may not appear to fit the traditional “romantic comedy” mold, but it follows the genre trajectory to a tee, even if it does so while singing out its own song.

Bud Cort stars as Harold Chasen, a young man who’s defined by an almost Thanos-level obsession with death. Ruth Gordon is Dame Marjorie “Maude” Chardin, a 79-year-old free spirit who knows a thing or two about making the most of one’s time on Earth. The chemistry between these unlikely friends (and lovers?) is pure comedy gold, as Harold follows Ruth around with puppy dog eyes, and Maude approaches the end of her life in a way that makes her new companion think about extending his own. She’s one of the movies’ greatest characters, at once electric with unpredictable eccentricity and grounded by the sort of wisdom earned only with age and experience.

Cat Stevens’ bop-laden original soundtrack does some of the heavy lifting for the romance side of things, while Harold’s escalating obsession with mortality and Maude’s flippant reactions to his provocations keep things light and lovestruck until the inevitable arrives. Forget Mrs. Robinson, Maude is the older woman of the thinking man’s dreams. —JD

32. “Love and Basketball” (Gina Prince-Bythewood, 2000)

UCLA grad Gina Prince-Bythewood ran track in college. At the center of her first feature, developed at the Sundance Institute’s directing and writing lab and produced by Spike Lee, she put into romantic conflict two L.A. athletes who are childhood sweethearts (Sanaa Lathan and Omar Epps). Over the years, as they play basketball through high school, college and into the professional leagues, they wrestle with complicated issues of love and friendship, competitiveness and gender identity, as they date other people and struggle with making it in the sport they adore. The sports romance broke out its two leads and writer-director, scoring over $27 million at the domestic box office. —AT

31. “Barefoot in the Park” (Gene Saks, 1967)

Famed New York theater writer Neil Simon brought his 1963 Broadway play to the big screen in 1967 with help from director Gene Saks (known for other stage-to-movie adaptations, including his 1968 spin on Simon’s “The Odd Couple”). Stars Robert Redford and Jane Fonda play Paul and Corie: a conservative lawyer and his whimsical wife working through the emotional beats of a marital comedy akin to “Green Acres” sans livestock. After the pair move into a walk-up Greenwich Village apartment, their differences are exacerbated by Paul’s buttoned-up job, Corie’s lonely mother Ethel (Mildred Natwick), and the couple’s zany new neighbors. —AF

30. “Boomerang” (Reginald Hudlin, 1992)

Eddie Murphy has never really played the traditional Hollywood romantic male lead. Of course, he was charming and adorable in “Coming to America,” but that was more of an urban fairytale than anything else. Despite his good looks, Murphy has seemed much more comfortable hamming it up in a fat suit, or underneath prosthetics, than seducing a woman on screen.

And yet that’s what makes 1992’s “Boomerang” such a wonderful outlier in his filmography. This slick, sophisticated, and immensely likeable rom-com afforded Murphy a rare opportunity to not just be handsome and charismatic, but also vulnerable, playing a high-powered lothario who’s undone by his search for “the perfect woman” when he meets someone he can’t seduce. Co-star Robin Givens keeps pace with Murphy every step of the way as the no-nonsense Jacqueline Broyer.

It’s a testament to Murphy’s skill as a leading man that you like his Marcus Graham even after he cheats on a young Halle Berry — the stacked cast also includes David Alan Grief, Martin Lawrence, Grace Jones, Chris Rock, and Eartha Kitt! — but his uncharacteristic softness proves irresistible.

“Boomerang” performed decently at the box office, but it seems to have left Murphy feeling a little too vulnerable, as he was soon back to hiding underneath fat suits in the “Nutty Professor” movies, voicing animated donkeys, and playing fathers who need to learn important lessons about life. —TO

29. “Annie Hall” (Woody Allen, 1977)

As with all of Woody Allen’s work, “Annie Hall” is hard to watch without thinking about some of the extra-textual baggage that it’s picked up over the years. But the film still feels strong enough to carry it, and Diane Keaton, Christopher Walken, and that poor lobster deserve to have their contributions recognized.

It’s easy to see in “Annie Hall” that writer-director-star Allen was in love with his leading lady, as together they created her ditzy, anxious, “la-di-da”–spouting, lovably awkward shiksa beauty with a terrifying brother (Walken) and “Jew hater” Grammy. “What did you do, grow up in a Norman Rockwell painting?” asks Allen’s Alvy Singer when he meets Annie at a Manhattan tennis club.

Soon they are an item, as Singer helps Annie battle a giant spider in her bathtub “the size of a Buick” and fights with her in line for a movie. That’s when he pulls over the real Marshall McLuhan to put in his place a pretentious man pontificating behnd them. Allen split the screen as Alvy and Annie each tells their shrink how little — or much — sex they’re having.

And he skewers Hollywood too: At a groovy party in the Hollywood Hills, Paul Simon invites Alvy and Annie to join him for a “mellow” gathering with Jack and Anjelica. “I don’t respond well to mellow,” Alvy says. “If I get too mellow, I ripen and then rot.” But the bittersweet romance carries the movie through, until inevitably, Alvy tells Annie, “a relationship is like a shark; it has to constantly move forward or it dies. And I think what we got on our hands is a dead shark.” How many unforgettable lines can one movie hold? “Annie Hall” broke the romantic comedy mold. —AT

28. “Muriel’s Wedding” (P.J. Hogan, 1994)

Before Toni Collette was officially branded as a “demi-goddess we don’t deserve,” she was the funny girl from “Muriel’s Wedding.” To Collette’s diehard fans — of which there are many — the infallible actress first won their hearts in this gut-punching Australian comedy by “My Best Friend’s Wedding” director P.J. Hogan, a cult favorite in which Collette plays a comely social outcast who dreams of a glamorous life far from her dead-end town (a dream shared by her best friend, played by Rachel Griffiths in another uncut gem of a performance). So Muriel enters into a green card marriage to a gorgeous South African swimmer, contorting herself into who she thinks she wants to be, rather than seeing the beauty in who she always was.

A comedy of errors that’s set to the tune of ABBA and punctuated with some truly wrenching moments, “Muriel’s Wedding” continues to speak (and sing) to anyone who sees themselves in all of the awkward movie archetypes who never get the guy (or girl). —JD

27. “Shakespeare in Love” (John Madden, 1998)

For an ingenious and absurdly charming movie that practically invented its own sub-genre of apocryphal storytelling on its way to grossing almost $300 million at the worldwide box office, John Madden’s “Shakespeare in Love” can’t seem to catch a break. First there was the fact that it “stole” the Oscar for Best Picture from “Saving Private Ryan,” a shock that doomed this delightful (and award-worthy) rom-com to be lumped together with the likes of “Crash.”

More recently, the film was tainted all over again by its unfortunate association with Harvey Weinstein — no other Miramax movie so epitomized his power as a producer, or furthered his ability to weaponize it against dozens of women over the decades to come.

But separate the movie from its baggage, and “Shakespeare in Love” holds up. For me, the first measure of a good rom-com is whether my stomach flips anytime the two would-be lovers look at each other. And with the chemistry between Joseph Fiennes and Gwyneth Paltrow radiating even through her ratty-mustached boy drag, “Shakespeare in Love” turns me inside out with every glance.

The second quality of a great rom-com is having that one iconic scene — the boombox outside the window or the “You Had Me at Hello.” Here, it’s undoubtedly the image of Paltrow spinning out of her boy drag and unwrapping herself into Fiennes’ hungry arms. With Stephen Warbeck’s score swelling in the background, it’s the moment that best epitomizes this movie’s undeniable alchemy.

Of course, Madden’s film is much more than a rom-com, though that distinction need not carry a whiff of snobbery. There’s a glorious and heart-swelling romance at its smoldering core, but Tom Stoppard and Marc Norman’s galaxy brain screenplay also contains intrigue, unforgettable supporting characters, and still the finest cinematic portrayal of William Shakespeare as a fully realized human being. How else could his ill-fated love story move us so? —JD

26. “Rangeela” (Ram Gopal Varma, 1995)

Ram Gopal Varma’s 1995 blockbuster follows an aspiring actress (Urmila Matondkar as Mili) in the Mumbai film industry who’s granted a shot at stardom when she catches the eye of famous leading man, Raj Kamal (Jackie Shroff). It’s a tale as old as time, but from that simple premise springs one of Bollywood’s fizziest rom-coms. The promising young newcomer has a chance to play the lead in a film opposite Raj when its headlining diva pulls out — or rather when the headlining diva’s mother pulls her out (“Does Julia Robert’s mother treat Spielberg like this?” its director asks).

It goes without saying that Raj falls in love with Mili, but the plot thickens when it’s revealed that Mili has a second man in her life, Munna (the iconic Aamir Khan), a street rat who’s also involved in the movie business (he scalps cinema tickets on the black market). 

“Rangeela” is Hindi for “colorful,” and if this film’s love triangle plays out in rather unsurprising fashion, the whole affair is rendered with so much energy and, well, color that it easily stands out amongst a crowded field.

This was musician A.R. Rahman’s Hindi-language debut, and it’s an absolute corker, as every song that’s played in the movie is more of an ear worm than the last. Varma shoots each number in the style of an MTV music video, delivering a global aesthetic before anyone was even talking about “transnational” cinema. The “Kya Kare Kya Na Kare (What To Do, What Not To Do)” sequence feels like the best Michael Jackson video never made, as the percussive banger unfolds across shadowy alleys full of faux-bad street toughs who only wish they were as big as their shadows. It’s one of the tastiest explosions of ‘90s cheese you’ll ever see. —CB

25. “Desk Set” (Walter Lang, 1957)

Many of Katharine Hepburn and Spencer Tracy’s movies haven’t aged particularly well, in part because they follow a retrograde formula: Hepburn is a disruptive force who Tracy has to “tame.” But one of their lesser-known pairings is an egalitarian confection: “Desk Set” doesn’t flip the script and have Tracy “get his” (though it comes close), but instead regards the two of them as actual equals.

Phoebe and Henry Ephron’s adaptation of William Marchant’s play has Hepburn as the head of a research department at a major broadcast network (obviously NBC, with 30 Rock even serving as the headquarters). For anyone who ever worked as a fact-checker, this will quickly take its place among your favorite films. She’s worried that the network is looking to downsize her and her team (Joan Blondell and Dina Merrill) in favor of a new invention: a computer. And who should the efficiency expert be who’s going to install this computer? Spencer Tracy. 

Fearing for the continued viability of one’s profession in light of automation apparently leads to great romantic sparks because Tracy and Hepburn are explosive here, even as Hepburn tries — and succeeds — to show the importance of retaining the “human element” in her work. “Desk Set” is also ahead of its time for showing the institutional sexism Hepburn’s character faces as a woman in media: She plays dumb in order to get the best of her longtime boyfriend (Gig Young), who also happens to be her boss.

The idea that romance can lead to self-actualization would provide the prototype for so many rom-coms to come (“Bridget Jones’s Diary” most of all), as Bunny doesn’t just trade in a crap boyfriend for a nice guy, she owns who she really is in the process, demands to be valued, and makes a dramatic workplace stand for the integrity of her career. —CB

24. “Notting Hill” (Roger Michell, 1999)

It’s hard to pick just one Hugh Grant rom-com to rule them all — “Music & Lyrics,” “Two Weeks Notice,” and of course “Four Weddings and a Funeral” were all seriously considered for this list — but “Notting Hill” stands out for its simplicity. Sure, movie star Anna Scott (Julia Roberts) is one of the most famous people on the planet, and it takes some of Richard Curtis’ most cringe-inducing contrivances to spark her romance with a flopsy British man who runs a travel book shop (because 1999 belongs to a different civilization), but at the end of the day she’s just a girl, standing in front of a boy, asking him to love her. 

Grant’s almost terminal self-pity and Roberts’ sometimes overpowering stridency make them perfect foils for each other, and director Roger Michell works with Curtis to create an immaculately well-calibrated story around them. The “Horse & Hound” sequence bends rom-com absurdity back towards itself, Rhys Ifans elevates the eccentric roommate character to an archetype all its own, and the rest of the supporting cast (highlighted by Hugh Bonneville, Gina McKee, and the late Emma Chambers) contribute to two of the most charming set-pieces you’ll ever find in a movie like this. The first is a dinner scene that bakes several different implausibilities into the saddest of brownies. The second is a climactic “race to the airport” that only needs a single gesture — and a Spencer David Group needle drop for the ages — to epitomize the demented appeal of an entire genre. When Roberts married regular human Daniel Moder three years later, it only made the fantasy of “Notting Hill” that much easier to believe. —DE  

23. “Pillow Talk” (Michael Gordon, 1959)

“Pillow Talk” marked Doris Day and Rock Hudson’s first movie together. And, while the performers’ instant chemistry can’t account for all of the 1959 romantic comedy’s myriad successes (Milton Carruth’s punchy editing is just too obviously excellent!) there’s no denying the spark that sets this meet-cute in motion. When a self-sufficient interior decorator is forced to share a telephone line with a womanizing writer, the pair begin a short-distance feud/flirtation (feud-tation?) that soon becomes a love triangle featuring Tony Randall and some romantic ’50s trickery. —AF

22. “Amélie” (Jean-Pierre Jeunet, 2001)

The popularity and unbridled preciousness of Jean-Pierre Jeunet’s 2001 rom-com have made it tempting to assume that “Amélie” may not hold up, but a re-watch confirms that this worldwide phenomenon has managed to weather decades of discourse and a short-lived Broadway musical to remain one of the best movies of its kind.

The sweetest and most sure-handed thing that Jeunet has ever made, “Amélie” is more than just the dazzlingly stylish story of a pixie-like Montmartre waitress (the breakout role of a lifetime for Audrey Tautou), it’s a humane and enduringly relevant portrait of a person who loves people but can’t quite bring herself to join them. 

The archetype may stretch all the way back to the likes of Jane Austen — there’s more than a little “Emma” in this fantastical tale of romance at a remove — Amélie is also the perfect heroine for the internet age that she just anticipated, as she predicted a time when everyone likes to a meddle in other people’s business while living their own lives from a safe distance. Her journey from fantasy to reality is as full and heartwarming and brave as ever, and Yann Tiersen’s soul-stirring accordion score leaves you feeling a little bit more in love with life itself. —DE

21. “The Lady Eve” (Preston Sturges, 1941)

A classic of the 1940s romantic screwball comedy genre, Preston Sturges’ “The Lady Eve” stars the great Barbara Stanwyck as a skilled con artist who sets out to steal money from the heir to a wealthy business empire (Henry Fonda), only to end up falling in love with him instead. What are the odds!

The traditions of the screwball comedy are all honored here, from the rapid-fire dialogue (“I could imagine a life with you being a series of ups and downs, lights and shadows, some irritation, but very much happiness” Fonda submits to his love interest), to the fast-moving set pieces — the film mostly takes place on an ocean liner, a one-setting hook that ratchets up the comic intensity with consistently sensational results — but it’s Stanwyck and Fonda’s sizzling chemistry that elevates the romance to iconic status. Sturges’ script makes the smart choice of having Fonda’s character being the naive and helpless romantic foil to Stanwyck’s strong-willed con artist, while the iconic actress exudes a sexual confidence that knocks Fonda right off his feet, and fells everyone on our side of the screen along with him. —ZS

20. “Sabrina” (Billy Wilder, 1954)

No one was able to explore the darkness of humanity in the guise of an impossibly entertaining studio comedy quite like the great Billy Wilder. The world of the wealthy Larrabees is full of glitz and glamour, making it understandable that their chauffeurs’ daughter (Audrey Hepburn) grew up obsessed with their playboy son (William Holden), and dreamed of marrying into his family.

But these characters are all so deeply fucked-up – the movie beginning with a suicide attempt – that untangling this bizarre love triangle (Humphrey Bogart playing the cold older brother) first requires these fragile characters to find solid ground. Hepburn is at her most delightful as a troubled young woman who blooms into self-discovery when she goes abroad to study cooking in Paris, only to come back with a more capable new perspective on the world of class stratification that brought her so much pain before.

Unfortunately, like most Hepburn films of this time, you just wish she could find someone to love who wasn’t twice her age. —CO

19. “Jerry Maguire” (Cameron Crowe, 1996)

He had her at “hello.” 

“Jerry Maguire” may not seem to fit inside the narrow parameters of a prototypical rom-com, but that’s only because there’s so much happening in this six-course meal of a movie that its romance can sometimes feel like an afterthought. And yet, if there’s one thing that Cameron Crowe’s Oscar-winning charm offensive has in common with the James L. Brooks films that inspired it, it’s an intractable preoccupation with the role that love is allowed to play in our lives — in our competitive, cynical, self-involved, uncompleted lives. 

Played with implosive desperation by a career-best Tom Cruise (whose performance defines “sweat equity” better than a dictionary ever could), the titular sports agent finds himself having to negotiate the terms of his own life after he gets fired for taking a stand against the soullessness of his profession. The one person who agrees to go with him? Judy Garland herself, Renée Zellweger (an actress who has yet to rediscover the same kind of both-feet-on-the-ground vulnerability that she displayed as Dorothy Boyd). Their stories intertwine and separate and knot back together while being pulled in several directions at once, but the rom-com genre offers few moments as spectacular and self-affirming as the line where Jerry realizes that love is the only thing that makes any of this shit worth doing in the first place: “I’m looking for my wife.” —DE

18. “The American President” (Rob Reiner, 1995)

Perhaps the most fantastical movie on this entire list, Rob Reiner’s smart, winsome, and unimpeachably adult-minded rom-com imagines what it might be like if the President of the United States were a handsome and charming man who struggled to reconcile his personal and political interests. A magical trial run of sorts for screenwriter/eventual “The West Wing” creator Aaron Sorkin (whose Beltway romanticism never fit better than it does here), “The American President” stars Michael Douglas as a widowed Commander-in-Chief whose re-election campaign is complicated by a major crush on an environmental lobbyist by the name of Sydney Ellen Wade.

Loaded with swoon-worthy moments (“My nervousness exists on several levels”), laced with razor-sharp dialogue, and shaped around a tolerably righteous exploration of the relationship between personal ideals and political realities, Reiner’s under-appreciated delight argues that love means never having to support a useless crime bill. Douglas’ climactic speech about gun control is still one of the most erotic moments in modern American cinema. —DE

17. “Clueless” (Amy Heckerling, 1995)

Jane Austen’s Regency-era comedies of manners (and, often, errors) have long proven themselves highly adaptable to modern times and contexts, but nothing quite compares to the contemporary charms of Amy Heckerling’s “Clueless.” At once a pitch-perfect high school comedy and a lovingly made twist on Austen’s “Emma,” the ‘90s-era classic also finds plenty of time for the many (many) romances that populate its source material.

There’s Dionne (Stacy Dash) and Murray (Donald Faison) who, when they think no one is watching, are so considerate of each other! Mr. Hall (Wallace Shawn) and Miss Geist (Twink Caplan) stumble into a somewhat engineered romance that ends the film with a star-studded wedding. Travis Birkenstock (Breckin Meyer, playing the most perfectly named character in Heckerling’s oeuvre) and delightfully ditzy Tai (the late Brittany Murphy) turn their slacker charms on full force (enough that even a skateboarding competition takes on gravitas). Hell, even Elton (Jeremy Sisto) and Amber (Elisa Donovan) find the lid for their (image-obsessed) pots. 

Most heartening, however, is the seemingly mismatched pairing of Cher (Alicia Silverstone, still never better) and Josh (Paul Rudd), retrofitted here into ex-step-siblings (still less awkward than Austen’s original concept, in which he’s a friend of Emma’s dad, like that’s normal) who can’t help but see the best in each other. Heckerling and her cast gamely navigate around the weird stuff, with Silverstone and Rudd’s chemistry and care for each other shining through in even the weirdest of moments (has a well-timed pigtail toss ever been this adorable?). The best part? It doesn’t end in a wedding, because this is California, not Kentucky! —KE

16. “Groundhog Day” (Harold Ramis, 1993)

Often imitated (including by the recent Sundance hit “Palm Springs”) but never surpassed, “Groundhog Day” is by design one of the most rewatchable movies on this list. Watch this Harold Ramis classic enough times and you’ll discover (at least) three remarkable things: One, the unlocking of Bill Murray’s true potential as a comic star with the full depth of the cosmos itself (a gift later exploited by the likes of Wes Anderson and Sofia Coppola). Two, a poignant and casually profound life lesson that mixes “It’s a Wonderful Life” with Buddhist philosophy, and somehow does justice to both the complexity and the simplicity of the ideas that result from that swirl; Murray’s curmudgeonly weatherman is revealed to be his own worst obstacle, and Andie MacDowell’s sweetly baffled love interest is a vessel for him to learn how to live outside of himself. Three, a script that taps into the recursive power of cinematic storytelling in a way that no mainstream comedy had ever done before — it takes a certain genius to look at the likes of “La Jetée” and “Je t’aime, Je t’aime” and see a vehicle for the guy who starred in “Stripes.”

But the real secret of “Groundhog Day” is that, whether you’re watching it for the first time or the 40th, it always leaves a smile on your face. —CO

15. “But I’m a Cheerleader” (Jamie Babbit, 2000)

It’s hard to count the number of careers launched by this queer cult classic, the kind of movie for which terms like “offbeat” and “quirky” were invented. “But I’m a Cheerleader” made low-budget look cool, and beneath its disaffected remove was a love story as sweet and sexy as queer audiences deserve. Set in the present day with a hyper-retro aesthetic, the movie stars a young Natasha Lyonne as Megan, an innocent cheerleader sent to a rehab for gay and lesbian teens. (This was a few years before conversion therapy became a hot-button topic, and the brutality of the practice was known to general audiences.)

Of course, putting a bunch of gay kids in a house together is bound to create some sexual tension, and Megan‘s gay little heart stands no chance against the dark and brooding Graham (the always delightful Clea Duvall). Director Jamie Babbit delivers the best of both worlds with a genuine and touching romance that blossoms amidst a wildly entertaining satire; the movie is as funny and winking as its title, and an enduringly formative experience for any teenagers looking to fall in love with who they really are. —JD

14. “My Big Fat Greek Wedding” (Joel Zwick, 2002)

It’s a tale as old as time: A “frumpy” duckling whose family doesn’t understand her is whisked away from a menial job thanks to a handsome prince. Or something like that. “My Big Fat Greek Wedding” burst onto the indie scene as a runaway hit in 2002, blending ethnic rom-com elements of “Moonstruck” and the standard meet cute-centric sensibilities beloved to the genre, albeit with a fresh twist. Nia Vardalos wrote and starred in the film as Toula, a waitress whose true passions are overlooked by her eccentric and overbearing Greek family. John Corbett, hot off his “Sex and the City” stint, plays Ian Miller, a decidedly non-Greek (aka very white) man who falls for Toula just as she finds her voice and sets out on her own. The lovable ensemble cast featuring Michael Constantine, Lainie Kazan, Andrea Martin, Louis Mandylor, and Joey Fatone (yes, of *NSYNC fame) round out the cute comedy that will have everyone remembering what Yiayia means and that Windex really does cure everything. —SB

13. “The Apartment” (Billy Wilder, 1960)

Billy Wilder’s crowning achievement from 1960 won Best Picture, Best Director, Best Screenplay, Best Art Direction, and Best Editing at the Academy Awards, and is still widely regarded among the best romances of the 1960s. A box office success, co-written by Wilder and frequent collaborator I. A. L. Diamond, “The Apartment” tells the story of an ambitious if misguided man — played by the hilarious Jack Lemmon — who decides to let his bosses use his home for their extramarital affairs. But when Shirley MacLaine’s cute elevator operator character is caught up in the scheme, our hero is forced to consider his morality against snide situational comedy and an increasingly complex connection. —AF

12. “His Girl Friday” (Howard Hawks, 1940)

One crucial aspect of the much-discussed “Hawksian woman” is that director Howard Hawks had very little insight into femininity or what it meant to be a woman. In the clockwork precision of his cinematic worlds, the women characters were exactly like the men — driven by their work and its attendant codes — which is why his decision to take a Ben Hecht and Charles MacArthur play called “The Front Page” play and gender-swap protagonist Hildy Johnson into a woman (Rosalind Russell) didn’t require all that much alteration. Hildy is still her editor Walter’s (Cary Grant) best reporter, and all of the conflict between them is strictly professional, but in Hawks’ version the duo also used to be married.

That major twists adds several new layers to the screwball antics of the original text, but what drives the film (and its director) is the fire and thrill of tabloid reporting. That energy is palpably channeled through the rapid-fire dialogue that Grant and Russell deliver at each like they’re Ford vs. Ferrari, and Hawks’ singular gift for rhythm and timing still runs laps around anything made today. —CO

11. “Moonstruck” (Norman Jewison, 1987)

Described by undervalued Hollywood director Norman Jewison as “an operatic multi-generational romantic comedy,” “Moonstruck” turned Cher into an Oscar-winning movie star thanks to her role as a tamped-down widow who freaks out her sprawling Brooklyn Sicilian family, led by matriarch Rose (Olympia Dukakis).

It all starts when Cher’s Loretta Castorini pays a visit to the bakery run by her fiancé’s younger brother, Ronny (then-breakout star Nicolas Cage), who refuses to let her marry his sibling (a less eligible Danny Aiello). Ronny refuses to let Loretta go through with the marriage – “the storybooks are bullshit! I want you to come up stairs with me and get in my bed!” — and a love story for the ages is born. Not since Rhett Butler seduced Scarlett O’Hara has a woman woken up so refreshed.

Cher instantly turns back into Cher. And when Ronny tells Loretta he’s in love with her, she slaps him. “Snap out of it!” No one involved in this heightened New Yawk confection thought it would become anything special, but Jewison knew exactly what he was doing. “That’s Amore,” indeed. —AT

10. “Monsoon Wedding” (Mira Nair, 2001)

Mira Nair’s best movies are reliably also her most challenging, independent and personal. That’s been true from the days of her Oscar-nominated feature debut, 1988’s vérité-style “Salaam Bombay!,” and it’s held up through the highs and lows of a brilliant career that now runs the gamut from “Mississippi Masala” to “Kama Sutra: A Tale of Love.”

In her joyful and gorgeously textured masterpiece “Monsoon Wedding,” Nair threads several romances through a tumultuous family drama which culminates in an arranged marriage between Aditi (Vasundhara Das) and Texas emigre Hemant (Parvin Dabas), whom she comes to know in the weeks leading up to their sudden nuptials. Nair expertly navigates the colorful subplots and local decor with constantly moving handheld cameras and an impeccable eye for detail, and there’s never a dull moment as the unfamiliar young lovers make their way towards a most satisfying finale.

If the plot doesn’t quite square with the expected mechanics of a romantic comedy, the newness of Aditi and Hemant’s match — along with the sheer ecstasy with which it burns into our hearts — allows “Monsoon Wedding” to capture the flame of new love better than many of the plainer genre offerings on this list. —AT

9. “Pretty Woman” (Garry Marshall, 1990)

Originally envisioned as a dark indie drama about the underbelly of Hollywood — hell, it even went through the Sundance Institute, so its independent cred runs deep — this Disney-financed hit put Julia Roberts (and her laugh) on the map thanks to the insane magic of a film that hinges on a “hooker with a heart of gold.” No, it doesn’t make sense on paper either. Much like other entries on this list, the spine of Garry Marshall’s movie is crafted around a classic tale (yes, it’s another “Pygmalion” story), but the heart is all in Roberts’ full-force star turn as Vivian. 

Despite its predictable storyline, Marshall found plenty of surprises to bolster its charm: the unexpected match of Roberts and co-star Richard Gere, a series of supporting stars that run the gamut from the divine (Hector Elizondo, Laura San Giacomo) to the terrifying (a deeply unsettling Jason Alexander), and one hundred percent Grade A romance in an extremely un-Disneyfied package. Still, nothing is better or more emblematic of why this all works so well than a notoriously unscripted sequence in which Gere’s Edward chomps down on Vivian’s hand with a lush jewelry box. Roberts’ laugh — reportedly all real — is pure joy. 

Penned by sole-credited writer J.F. Lawton, the first draft of the movie was titled “3000,” referring to the amount of money Edward was going to pay Vivian for a week of her services, and it ended the story on a very dark note. Marshall used his take to subvert the princess in a castle fairy tale with a knowing wink. In the end, it’s Vivian who rescues Edward, and the rom-com genre along with him. —KE

8. “The Shop Around the Corner” (Ernst Lubitsch, 1940)

Ernst Lubitsch’s adaptation of Miklos Laszlo’s play “Parfumerie” is a love story taken to the point of abstraction: two pen pals in Budapest have fallen in love with each other through their words alone. Little do they know that they actually know each other. In fact, they’re actually feuding co-workers (Margaret Sullivan and Jimmy Stewart) who hate each other with the passion of a thousand suns.

But the anonymity that comes from writing one another empowers them to reveal their best selves. Would their affection for each other survive if they actually knew their beloved pen pal is someone who makes their day job miserable? 

The premise was recycled for Nora Ephron’s beloved AOL-era remake, “You’ve Got Mail” (the Judy Garland/Van Johnson remake “In the Good Old Summertime” is also recommended), but none of the subsequent versions can hope to compare with Lubitsch’s original. Each character in the ensemble is richly drawn — with apologies to “The Apartment,” this is one of the only movies ever to successfully mix humor with the drama and sadness of an attempted suicide — and none of the emotions are underlined for emphasis through close-ups, aggressive cutting, or even music.

In fact, the film has almost no score at all except over the titles. But it’s always honest and heart-rending, as it is in the moment when Sullivan’s character’s hand reaches into her P.O. box hoping a letter from her beloved will be there, only for his hand to go limp as it swats at the empty air; the Lubitsch Touch can be electric and crushing in equal measure. It all builds to the final reveal: who are the real people here? The feuding coworkers or the idealistic lovers? Maybe a little bit of both. If their romance endures it’s because they’ve already experienced not just the highs of love, but the lows as well. —CB

7. “Bringing Up Baby” (Howard Hawks, 1938)

“Meet-cute” has become shorthand for scenes in which two lovestruck characters are (often awkwardly) first introduced, and Howard Hawks’ brilliant “Bringing Up Baby” — the most screwball of all rom-coms — might be thought of as a series of increasingly horrifying meet-cutes that multiply and compound each other for 102 hilarious minutes.

The unlikely couple here are extreme versions of common genre archetypes. Cary Grant plays absent-minded paleontologist David Huxley, who — on the eve of his wedding to another woman — gets entangled with ditzy heiress Katharine Hepburn. The “Baby” of the title? Well, that’s obviously her pet leopard, who is central to the wacky events that turn David’s life into glorious shambles and lead the film’s hopeless human leads towards the discovery that that opposites can spark an attraction that neither ever expected to experience.

The least conventional of great romantic comedies is so enduringly wonderful because of how it celebrates lunacy at every turn, defying the conventional thinking that is often at the core of this genre. It was too radical for audiences and critics back in 1938 (when it belly-flopped at the box office), but from today’s perspective it seems like one of the funniest movies ever made. —TB

6. “Forgetting Sarah Marshall” (Nicholas Stoller, 2008)

“Dracula musical!” 

The greatest and most endlessly rewatchable thing that resulted from the golden age of Judd Apatow man-children, Nicholas Stoller’s brokenhearted masterpiece isn’t only the funniest movie on this list, it’s also one of the wiser and more honest portraits of how the right kind of hurt can help steer you away from the wrong kind of happiness. Jason Segel — who was only 25 when he wrote the semi-autobiographical screenplay (a Wellesian flex that might inspire some historians to think of this movie as the “Citizen Kane” of its time) — stars as Peter Bretter, a creatively stunted composer who gets dumped in savage fashion by his TV star girlfriend, Sarah Marshall (a brilliantly self-involved Kristen Bell).

Desperate to get away for awhile and clear his head, Peter flees to a Hawaiian resort… only to discover that he’s trapped in paradise with Sarah and her new boyfriend, hedonistic rocker Aldous Snow (Russell Brand in the role that he was born to play). 

Lucky for Peter, love is all around, and he’s soon flirting with the beautiful hotel receptionist played by an off-the-charts charming Mila Kunis. He’s also sobbing his way around an unimpeachable supporting cast that includes Jonah Hill as a starstruck waiter (“did you get it? “Did you get it?”), Paul Rudd as a terminally dumb surfing instructer who feels like a live-action Pixar character (“you sound like you’re from London!”), Bill Hader, Da’Vone McDonald, Jack McBrayer, and a dozen adorable blood-sucking puppets.

Every line is gold, every scene is loaded with shaggy comic purpose, and the impromptu double date in the second half might represent the finest cinematic achievement of the 21st century (“take my eyes but not the shirt!”). Top it off with an Oscar-worthy ballad about Dracula’s cursed love life and some hardwon self-respect and you have a romantic comedy that deserves to be considered alongside the very greatest examples of the genre. —DE

5. “Roman Holiday” (William Wyler, 1953)

The star-making performance to end all star-making performances, Audrey Hepburn’s breakout turn in “Roman Holiday” was so clearly a piece of history in the making that leading man Gregory Peck insisted that his unknown co-star recieve equal billing. Hepburn is nothing short of magical as the sheltered princess at the heart of William Wyler’s modern fable, the doe-eyed young actress playing the part of a fugitive royal with an enchanting mix of naiveté and sophistication.

The plot around her couldn’t be simpler: Desperate for a reprieve from her tightly controlled life, Princess Ann sneaks out of her country’s embassy during a state visit to the Italian capital. And wouldn’t you know it, the first person she meets just happens to be expat reporter Joe Bradley (Peck), who sees his bubbly new friend as a lucrative potential story, and pretends not to know her real identity as he shows her the sights. What follows is a Hollywood love story at its finest, flecked with golden moments (the Mouth of Truth sequence comes to mind) and bound to the same kind of bittersweet energy that would later fuel Richard Linklater’s more contemplative “Before” trilogy. Hepburn and Peck are immortal together — the casting allows Dalton Trumbo, Ian McLellan Hunter, and John Dighton’s script to get away with the fairy tale dynamics — and the wistful ending is one of the sweetest gut-punches ever landed on the screen. —DE

4. “When Harry Met Sally” (Rob Reiner, 1989)

“I’ll have what she’s having.” “You look like a normal person but you’re actually the angel of death.” “Waiter, there is too much pepper on my paprikash.” “Baby fish mouth.” And that’s just off the top of my head.

Director Rob Reiner and writer Nora Ephron’s endlessly quotable “When Harry Met Sally,” a more-than-obvious yet loving ode to “Annie Hall,” set the gold standard for all romantic comedies that followed once it was released in 1989. Try not to fall in love with Meg Ryan — feathered hair, knee socks, shoulder pads, and all. Then there’s Billy Crystal as her oddly adorable, hopeless misanthrope of a former adversary, with whom Ryan shares the kind of lived-in neurotic chemistry that’s hardly been seen in American movies since (the “Seinfeld” vibe between Jerry and Elaine might be the only thing that comes close).

Carrie Fisher brings her dry, singular deadpan as Sally’s pal Marie, whom Ryan’s character sets up with Harry’s bestie Jess, played by Bruno Kirby. It all makes for an unusually low-key, tender effort from Reiner, and one entirely devoid of schmaltz.

Can men and women really be friends, or does the attraction always get in the way? The jury’s still out on that one, but it’s never been so much fun to watch two people ask themselves the question. —RL

3. “Broadcast News” (James L. Brooks, 1987)

Sparks fly and journalistic integrity goes up in flames during James L. Brooks’ inimitable “Broadcast News,” which reconfigures a woman’s choice between two very different men as an existential tug-of-war between hard news and infotainment. Brooks’ zippiest film (despite its shrewd and unflinching look at office gender politics and the struggle to break the glass ceiling), this endlessly quotable masterpiece is brought to life by one of the most winning triads ever assembled.

Albert Brooks has never been better than he is as the nebbishy Aaron Altman, a gifted reporter who does his best work off-camera. William Hurt is perfect in the role of handsome dolt Tom Grunick, who anchors the news with corn-fed swagger and the purest “high school jock who was cast as the lead in the school play” energy you’ll ever see on a movie screen. And Holly Hunter gives one of the greatest performances in all of movies as the workaholic Jane, a whip-smart producer who shares Aaron’s brain and Tom’s bed. 

The three characters jockey for the spotlight as Aaron and Tom compete for Jane’s affection, all against a high-pressure newsroom environment that provides perfect terrain for a Hawksian rom-com with a modern sensibility. Not just “modern,” but prescient in the way that Brooks anticipated how seductively 24-hour news would come to rot this country from the inside out. The famously awkward ending may not be satisfying in the ways you expect, but it stings with bittersweet truths and helps to liberate “Broadcast News” far beyond its genre trappings. —DE

2. “It Happened One Night” (Frank Capra, 1934)

This deliciously satisfying Oscar-winning Claudette Colbert/Clark Gable romance holds up eight decades later because it’s a much richer meal than just the much-imitated rom-com prototype of a poor little rich girl who runs away from her controlling daddy (Walter Connolly) who’s right to block her rebellious marriage to a gold-digging airman (Jameson Thomas). But headstrong Ellie Andrews (Colbert) has to figure that out for herself. As her flight makes tabloid headlines, she hits the road incognito, first on a bus, where she’s spotted by freewheeling newspaperman Peter Warne (Gable) who smells a story, looks after her, and when they flee from a nosy parker, teaches her how to hitchhike. In that classic scene, even though she’s learning what it means to go hungry, she disdains a carrot, but after Peter fails to catch a ride with his thumb technique, she knows to pull up her skirt and flash some gam.

Ellie keeps surprising Peter, throwing him off-balance. That’s just one of many classic scenes in this dark-edged Depression fable, which also inspired Cameron Crowe’s “Tiny Dancer” bus singalong in “Almost Famous.” (In this case, it’s “The Man on the Flying Trapeze.”)

True to the period, the filmmakers had to devise a clever way to allow the couple falling in love to shack up in the same motel room. Their solution: The Wall of Jericho, which inevitably, comes tumbling down. —AT

1. “The Philadelphia Story” (George Cukor, 1940)

Katharine Hepburn was box office poison when she got Howard Hughes to help her acquire film rights to her Broadway smash, Philip Barry’s delirious class comedy “The Philadelphia Story.” George Cukor directed her best movie ever, which won two out of six Oscars for Jimmy Stewart and screenwriter Donald Ogden Stewart. Tailor-made for the athletic Connecticut actress was the role of imperious, entitled Tracy Lord, who is at the center of two love triangles. Everyman reporter Macaulay Connor (Jimmy Stewart) worships socialite Tracy, watched by his stoic photographer (Ruth Hussey), who loves him.

And as Tracy rushes headlong into marriage with straight-edged George Kittredge (John Howard), whom her entire family dislikes, she has no clue how much she still adores her critical ex-husband, C.K. Dexter Haven (Cary Grant), who wants her to come down off her high horse, but doesn’t want her to marry George either.

The highlight of the movie is a moonlit night by the pool as a drunk and besotted Macaulay tells Tracy how magnificent she is: “You’re lit from within, Tracy. You’ve got fires banked down in you, hearth-fires and holocausts.” When everything falls into place, as Tracy and her father walk down the aisle toward Dexter, she asks, “How do I look?” Her father says, “Like a queen. Like a goddess.” Tracy says, “And do you know how I feel? Like a human. Like a human being.” It doesn’t get better than that. —AT