1. Trouble In Paradise
The meet-cute is one of the many standard and stale features of romantic comedies, but there’s never been a better one than the charming encounter between two professional thieves in Ernst Lubitsch’s screwball classic. Herbert Marshall and Miriam Hopkins, both extraordinary pickpockets, rob each other blind over dinner and fall in love in the process, each dazzled by the other’s sly artistry. (When Hopkins admits she lifted Marshall’s wallet, he replies, “I know, you tickled me, but your embrace was so sweet.”) Their efforts to fleece a perfume-company heiress who’s wilier than she seems run into complications, but the outlaw chemistry between them never diminishes.
2. Say Anything… (1989)
Cameron Crowe’s directorial debut Say Anything… is the gold standard for high-school romance movies. Lloyd Dobler—played by John Cusack, who still gets laid daily because of this movie—is a lot less cocksure than the typical male teen protagonist, who’s generally less interested in love than in having a last crazy summer before shipping off to college. Dobler is just a kind, decent kid, not an obnoxious hormone factory. He’s perfectly complemented by Diane Court (Ione Skye), a sensible, seemingly perfect honors student whose beauty belies the kind of profound loneliness that hits people between the ages of 16 and 22. People who had tons of mind-blowing, soft-focus sex in high school probably won’t relate to Say Anything…; everyone else will remember the awkwardness and confusion that goes hand in hand with the exhilaration of falling in love for the first time.
3. Romeo & Juliet (1968)
Aside from the gorgeous language and the classic story, what makes William Shakespeare’s story of star-crossed lovers so enduring is its believability. No, not the magic potions and other dramatic trappings: the behavior of the lead characters, who are so completely taken with each other that they defy their families, their friends, and every scrap of common sense they possess just to be with each other. That’s the narrative that’s believable only to the teenage mind, and that’s why it’s endured for 400 years. Every generation of high-school kids forced to read Romeo & Juliet gets to gasp in recognition as they think, “That could be me and my tweaked-out boyfriend!” The play has been filmed roughly a million times, but the quintessential version is Franco Zeffirelli’s; he had the inspired idea of casting actual teenagers in the role (Leonard Whiting and the breathtaking/naked Olivia Hussey), and ramping up the heated sexual element to make the movie vibrate like a bell with the sort of overwhelming, end-of-the-world importance that teenagers assign to their first crushes.
4. West Side Story (1961)
It would be criminal to mention Romeo & Juliet without giving props to West Side Story, its legendary musical adaptation by playwright/screenwriter Arthur Laurents, composer Leonard Bernstein, and lyricist Stephen Sondheim. It’s a perfect illustration of why musicals, at their best, are so magical, and why of all the art forms, music speaks so purely to love; numbers like “I Feel Pretty” capture better than words alone how knowing someone loves you can make you feel beautiful, strong, and powerful. While West Side Story retains the tragic qualities and bloody ending of Shakespeare’s play, it allows for moments of lightness along the way; where Zeffirelli allowed the brutal, undeniable passion of teenage romance to burn up the screen, directors Jerome Robbins and Robert Wise let the playfulness and gentle teasing of the social milieu creep in and leaven the dark moments to come. When it takes itself seriously, West Side Story is just as effective a portrayal of the fiery nature of teen passion, but when it lets a little light in, it also recalls why it’s so much damn fun to be in love at that age.
5. Before Sunrise (1995)
Falling in love requires a leap of faith, a moment of saying, “Yes, let’s see where this goes.” Such moments are rarely so sharply timed as the one in Before Sunrise, which requires Parisian Julie Delpy to decide whether to get off a train in Vienna to spend the day with charming new acquaintance Ethan Hawke before he flies back to America. She does, and the two spend the rest of the movie talking honestly and openly as they walk around the town. With nothing to lose, since they’ll never see each other again—well, maybe—they hold no thoughts back, and their connection goes deeper than superficial attraction. They’re two people about to enter the scary world of adulthood, but for at least one night, they belong alone together.
6. Roman Holiday (1953)
Far too many modern romances have a couple tumbling into a relationship (or just into the sack, which then becomes a weird movie shorthand for an eternally perfect connection) after a gimmicky meet-up and a minor adventure that redefines their lives. But few of those films hold a candle to Roman Holiday, which does the genre right. Audrey Hepburn plays the princess of an unspecified country; Gregory Peck is a reporter who tries to take advantage of her when she ditches her escorts and spends a day exploring Rome. Over the course of the day, as they get to know each other, he softens his journalistic zeal and is so taken by her love of life and experience that he learns to just enjoy her company, while she in turn sees him as representative of a whole world she’s been locked away from. It’s profoundly charming, and it also indelibly captures those first moments when two strangers move past cordial distance and start seeing each other as real, then as special, then as essential.
7. It Happened One Night (1934)
The romances in some classic movies are distractingly old-fashioned, but something about the burgeoning attraction between Clark Gable and Claudette Colbert in Frank Capra’s 1934 It Happened One Night still seems fresh, flirty, and believable 75 years after the film was released. She’s a spoiled rich girl on the run from her father and fiancé. He’s a jug-eared, washed-up journalist tailing her for a story. But instead of making Gable the hero and Colbert the brat in need of a lesson, the two leads are equally, charmingly flawed, and they fall into a teasing, sarcastic relationship with a witty give-and-take on Seinfeld-esque topics such as the best way to dunk a donut, or what constitutes a piggyback ride. Banter! There’s no grand moment where they fall in love: They simply become more of a team, pretending to be a married couple to escape detection, and teaching each other the vagaries of hitchhiking. Rarely do script and actors come together to create a believable, casual rapport where the performers genuinely seem to be entertaining each other. The healthy dose of (subtle, tasteful) sex doesn’t hurt—from the sharp slap on the ass Gable gives Colbert as he carries her across a stream to the legendary “walls of Jericho” scene to the end of the movie, where the reunited couple returns to their roadhouse trailer to do it. Kinky.
8. A Perfect Couple (1979)
Robert Altman wasn’t exactly known for his sentimental streak, but his movies have featured a romantic couple or two. The fast-burning, doomed love of Keith Carradine and Shelley Duvall in the revisionist gangster picture Thieves Like Us comes to mind, as does the far happier connection between Paul Dooley and Marta Heflin in the L.A.-centric musical-comedy A Perfect Couple. In the latter, Dooley is a middle-aged square under the boot of his domineering Greek father, while Heflin is a vocalist in a sprawling rock ensemble. They meet via a computer dating service, have a disastrous first encounter, but then begin to find in each other a way out of their respective family dramas. This perfect couple leaves their fathers and mothers and cleaves to each other—just like it says to do in the Bible.
9. Holiday (1938)
The writing-directing-acting team behind the 1940 romantic comedy classic The Philadelphia Story struck a couple of years earlier with the lesser-known but equally wonderful Holiday, which could almost be the giddy prequel to the more acerbic Philadelphia. Cary Grant plays a successful up-by-his-bootstraps businessman who’s ready to leave the rat race behind and pursue a life of poetry and philanthropy. The problem? He’s engaged to be married to an heiress whose family expects him to suppress his free spirit and keep earning. The possible saving grace? His fiancée’s sister, Katharine Hepburn, is completely enthralled by his idealism, even though he worries that she’s just a dilettante looking to rebel against her family. Though they don’t entirely trust each other, they’re obviously soulmates, and as they inch closer together, their kinship becomes almost like a dare.
10. Barcelona (1994)
The Spanish girls that Chris Eigeman and Taylor Nichols date in Whit Stillman’s culture-clash comedy Barcelona don’t care for the Americans’ limited sense of culture or their inadvertent imperialism, but they’re still open-minded enough to sleep with them. Yet the rigidly ethical Nichols—a firm believer in the healing power of American business—is looking for something more than just a fling, and finds it only after Eigeman gets shot, and Nichols is joined in his bedside vigil by a woman as faithful as he is. Discovering true love in the revelation of shared ideals: That’s a happy ending in Stillman-world.
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11. Brokeback Mountain (2005)
For all the talk about Brokeback Mountain as a groundbreaking film about gay lovers, what really makes the story work is its depiction of love as a kind of lucky escape: how fortunate Heath Ledger and Jake Gyllenhaal are to find each other in the middle of nowhere, and how eagerly they look forward to the few times a year they get to reunite. Gay or not, anyone who’s ever been in a long-distance relationship can identify with the feeling that the time spent with a beloved partner is portioned off from everyday life—so sacred and rare that it’s almost unreal.
12. Summertime (1955)
In David Lean’s Summertime, Katharine Hepburn plays a middle-aged Ohio spinster who arrives in Venice for her dream vacation. She’s an independent, no-nonsense secretary who just wants to capture the sights with her 8mm movie camera. But the city charms her with its impudent children and languorous canals, and an antiques dealer woos her over coffee in the Piazzo San Marco. Hepburn captures just the right note as an aging woman who doesn’t think love is in the cards for her: cautious, wistful, and just a little sad, even as she’s giving her heart to Venice in the summertime. All trips to Europe should be this romantic.
13. I Know Where I’m Going! (1945)
Wendy Hiller knows exactly what she wants out of life: an advantageous marriage and another step up the social ladder. But when directors Michael Powell and Emeric Pressburger trap her on a remote island on her way to her wedding in I Know Where I’m Going!, her best-laid plans go awry thanks to the wry smile of Roger Livesey, a Scottish lad who fills her empty days with ruined castles and folk dancing. It shouldn’t take nearly drowning in an ill-advised channel crossing for Hiller to see that the dashing Livesey is her man, not the boring offscreen industrialist. If he told us about the old tradition of making a wish the first night under his roof, we wouldn’t waste any time asking if we could count the beams in his bedroom instead.
14. Friday Night (2002)
One-night stands are usually tawdry, but Claire Denis’ magical dusk-’til-dawn romance is like Before Sunrise without all the chatter: a vibrant fantasy about two Parisians who meet for one enchanting evening and part ways in the morning. For the heroine (Valérie Lemercier), the chance encounter with a ruggedly handsome stranger (Vincent Lindon) is a reprieve of sorts, one last fling before she moves into her boyfriend’s apartment the next day. They meet in the middle of an endless traffic snarl—she’s driving, he wants a ride—but wind up escaping the cacophony in quiet cafés and a pizza joint, until finally stealing away for a brief, passionate hotel rendezvous. Deliberately minor in scale, Friday Night brings the full force of Denis’ seductive style—and that of ace collaborators like cinematographer Agnès Godard and musician Dickon Hinchliffe of Tindersticks—to bear on what amounts to a great short story, one interested only in capturing a delicious moment out of time.
15. Chilly Scenes Of Winter (1979)
Just because falling in love feels good doesn’t always mean it is good, an inconvenient truism explored in Joan Micklin Silver’s perceptive 1979 cult comedy Chilly Scenes Of Winter. John Heard is a needy man hung up on a recently ended affair with a married woman (Mary Beth Hurt), who complains that her husband doesn’t love her enough and that Heard loves her too much. She’s definitely right about Heard, whose love for Hurt is clearly genuine, but also overbearing bordering on obsession. While Heard and Hurt are often great together, they don’t really belong together. In Chilly Scenes Of Winter, as in real life, love sometimes suffocates our objects of affection, in spite of our best intentions.
16. Punch Drunk Love (2002)
Paul Thomas Anderson’s Punch Drunk Love flips the rom-com script by showing both of its principals as slightly maladjusted weirdoes. In a role he was born to play, Adam Sandler stars as a lonely toilet-plunger salesman who’s henpecked by seven sisters and understandably never dates. When Emily Watson comes along to court him, she seems relatively sane—too sane to be pursuing Sandler, at least—but it turns out that underneath the surface, they’re lonely and odd in similar ways. Their bedroom scene is remarkably sweet, as each lets repressed feelings rush out: Somehow, in these hands, lines like “I’m looking at your face and I just want to smash it; I just want to fuckin’ smash it with a sledgehammer and squeeze it” and “I want to scoop out your eyes and I want to eat them” become tender and believable.
17. Sideways (2004)
There are lots of movies about neurotic losers who find love, but few star a character as endearing and entertaining as Paul Giamatti in Sideways. Giamatti perfectly captured the cultured-yet-uncultured paradox of a snooty oenophile whose lot in life is teaching public school while clinging to his pathetic hang-up on his ex-wife and his hopes of selling his pretentious doorstop of a novel. Meeting Virginia Madsen only further stirs up his awkwardness. Giamatti slowly allows things to develop, with all the normal effects: letting go of old relationships, writing love letters, sharing personal aspirations and secrets, and eventually leaving everything behind on the chance it will work out. Like wine, love is sometimes best when given time to mature.
18. Wall-E (2008)
Imagine this pitch: Two robots originally incapable of emotion embark on a quest to save Earth, during which they learn how to love. Sounds awful, right? (Can’t you picture the guy in the scriptwriting session throwing out, “And they kiss through an electric spark through their heads!”?) But Wall-E was a Pixar project, so it’s one of the best films of the decade. The last remaining trash-stacking robot on a polluted, abandoned Earth, weirdly expressive hero Wall-E has developed a personality; the downside of that is crippling loneliness. When super-advanced robot Eve shows up, she’s much more than a deliverance from solitude. Taking tips from Hello, Dolly!, which he compulsively rewatches as a bewitching window to another, more romantic world, Wall-E begins an unrequited courtship, devotedly pursuing and protecting Eve. With feats of self-sacrifice on both ends, love eventually lets them transcend their designs. It’s that powerful and simple, whether you’re android or human.
19. A Matter Of Life And Death (1946)
Dashing RAF pilot David Niven and American radio operator Kim Hunter bond at a most inopportune time in Michael Powell and Emeric Pressburger’s classic romantic fantasy A Matter Of Life And Death. Hunter first comes into Niven’s life as the disembodied voice at the other end of the radio after Niven’s plane has taken enemy fire, his crew has bailed out, his parachute is shot up, and he’s facing seemingly imminent death. Not the cheeriest of openings for a romance, but it perks up when Niven ends up miraculously alive on a beach by Hunter’s base the next morning, and proceeds to fall hopelessly in love with her. The path of love seldom runs smoothly, however, and it turns out Niven was supposed to have died in the crash. Witty, sophisticated, and melancholy, A Matter Of Life And Death builds into a touching, profound meditation on death, fate, and the power of love, as well as a sly commentary on Anglo-American relationships.
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20. Once (2006)
Proof that the phrase “Let’s make beautiful music together” is sometimes something other than a filthy, filthy euphemism, Once is the story of a street musician (The Frames’ Glen Hansard) who meets a beautiful flower girl (then-unknown Markéta Irglová) who knows her way around a piano. Beautiful music ensues, as do the sweet, down-to-Earth moments of any early courtship; Hansard’s “Broken Hearted Hoover Fixer Sucker Guy” serenade—a tune about Irglová’s busted vacuum, sung with a smile on a public bus—is a perfect example. The sparks between the stars were real—Hansard and Irglová started their own cradle-robberish romance almost immediately after the film’s release. And though it didn’t last—they recently called it quits—Once still endures, preserving the moment on film.
21. Annie Hall (1977)
When we first see Woody Allen and Diane Keaton together in Annie Hall, their relationship is already in choppy waters, if not technically on the rocks. She’s late for a movie and already defensive, knowing he’ll flip if he isn’t there for the credits. There isn’t much going on in the bedroom, either. So how did it come to this? Allen’s breakthrough film answers the question while providing counterpoint scenes that show how their relationship began. And remarkably, the contrast plays as sweet rather than bitter. As in real life, Keaton and Allen don’t make it as a couple, but Annie Hall captures the getting-to-know-you phase of their relationship in all its tender awkwardness (“Where did you grow up? In a Norman Rockwell painting?”), and keeps suggesting that love is worth any chance of eventual heartbreak, and that maybe getting your heart broken isn’t the worst thing in the world, either. It’s the rare date movie that could double as a break-up note.
22. Roxanne (1987) (LP)
Edmond Rostand’s Cyrano De Bergerac is every homely nerd’s favorite love story. The title character is a brave leader, a fierce warrior, a scintillating wit, and a poet of such transcendence that all he’d have to do is speak to a beautiful woman and she’d fall in love with him—if not for the superficial quality of his gigantic honker. What’s not to like? Unfortunately, as a pure romance, it’s a bit of a downer; Cyrano is too filled with anger, and his love for Roxanne is a tragedy: she only realizes it was him she loved all long when he’s on his deathbed. In the breezy modern-day adaptation Roxanne, screenwriter-star Steve Martin keeps all the humor and lightness of Cyrano’s story, and erases the rage and regret. Not only is there a happy ending for everyone, but Rick Rossovich, playing an analogue of the handsome but shallow Christian, isn’t a contemptible blowhard, but a likeable doofus. At its heart, Roxanne is an ego-stroking wish-fulfillment fantasy for ugly people, but it’s such a winning one, it’s hard to care. Those who can suspend their disbelief enough to buy Daryl Hannah as an astrophysicist are in for one of the loveliest romantic comedies of the ‘80s.
23. My Summer Of Love (2004)
Bored working-class high-schooler Nathalie Press sees her dingy black-and-white world turn to radiant Technicolor when she meets Emily Blunt, a wild, flirtatious rich girl who treats life like a lark and ushers Press into a glamorous realm of sex, sense derangement, and lies in Pawel Pawlikowski’s hypnotic romantic comedy-drama Summer Of Love. But inveterate fantasist Blunt isn’t at all what she seems, and Press soon learns the messy, essential truth that the first great love of everyone’s life almost inevitably becomes the source of their first great heartbreak as well. In Pawlikowski’s elegant, powerful coming-of-age story, infatuation becomes a mood-altering state that mixes delirious disorientation with the tragicomic intensity and heightened awareness of adolescence.
24. Jules Et Jim (1962)
Having captured with stunning perfection the wonder and horror of childhood in The 400 Blows, it seemed impossible that François Truffaut could repeat the trick again with subjects as tricky as friendship and romance, yet he did—and in the same movie, no less. Jules and Jim would be a near-perfect movie about the constant jostling and rough affection of male friendship even without the presence of Jeanne Moreau, but once she appears, she so completely takes over the film that it’s transformed into an equally flawless movie about the delicacy and tragedy of romance. Truffaut was unparalleled at the creation of moments, and Jules Et Jim (the title belongs to the men just as surely as the movie belongs to the woman) is full of them, moments that will be as familiar as a heartbeat to anyone who has been not-so-secretly in love with their best friend’s mate. Aside from skillfully capturing the war between what the heart wants for its loved ones and what it wants for itself, Jules and Jim is astonishing at portraying how love can transform even dull daily rituals, such as when Henri Serre, having fully fallen for Moreau after she jumps into the Seine, decides to draw a picture of the scene—even though he doesn’t draw.
25. The Shop Around The Corner (1940)
They can’t stand each other, but they’re made for each other. That old romantic-comedy setup shouldn’t work, but The Shop Around The Corner has viewers rooting for Jimmy Stewart and Margaret Sullavan from the first moment it becomes clear that their secret pen-pals are… each other! It’s the way Ernst Lubitsch subtly twists the plot contrivances needed to keep the two apart for 90 minutes that makes the emotions so real. Stewart finds out the secret right away, but angry at rude treatment from Sullavan, he leaves her twisting in the wind. Through his eyes, the audience sees her transform as their circumstances change, and by the time the veil is lifted, the whole audience is probably flipping through mental rolodexes, wondering who among our officemates might have such a secret.
26. Defending Your Life (1991)
Poor Albert Brooks has to die and arrive at the afterlife’s processing center before he finally meets the love of his life: Meryl Streep, a good-natured woman who instantly makes the terminally neurotic Brooks feel “okay.” Much of Defending Your Life is about Brooks coming to terms with all the mistakes he’s made in his life—mostly due to fear—but the movie is held together by all the scenes of Brooks and Streep walking hand-in-hand through the ultimate resort spot, like kids who kissed one night at summer camp and now are spending every minute they can together before the bus comes to pick them up.
27. The Sound Of Music (1965)
Looking at the gimmick-ridden basic plotline of The Sound Of Music, it’s actually a wonder that it hasn’t already been remade as an obnoxious modern rom-com. Just strip out the songs, add some fart jokes for the guys and a pop hit for the gals, and plug in a sassy black or gay friend, and the story is as high-concept as anything this side of How To Lose A Guy In 10 Days: Julie Andrews is a sheltered nun who just doesn’t fit in at the convent. Christopher Plummer is a cranky widower with seven bratty children who drive away anyone who tries to take care of them. When Andrews and Plummer meet, first they hate each other, then they love each other! Meanwhile, the bratty kids cut up and play pranks, but eventually turn out to be sweethearts! Finally, they all perform at a concert! But the description doesn’t do justice to the execution, and The Sound Of Music is far more than the sum of its plotlines—thanks in large part to Plummer’s perfect martinet act and Andrews’ eternally warm, sweet smile. (Her aching sincerity ups the believability of any love story by 50 percent all on its own.) The songs and the sweeping epic tone help sell their relationship, but at heart, it’s just a well-performed story about two people who meet under trying circumstances and don’t get along, but gradually realize they’ve bonded over mutual admiration, respect, and need. Though it certainly helps that their romance isn’t the only story at work in the film, and it doesn’t end with a contrived squabble, a reconciliation, and a wisecrack.
28. Eternal Sunshine Of The Spotless Mind (2004)
As the J. Geils Band adroitly noted, love stinks, especially when it dies a spectacular death after a promising beginning. Michel Gondry’s crushingly bittersweet science-fiction romance Eternal Sunshine Of The Spotless Mind nails how our best romantic memories can be turned sour by the dark places relationships inevitably travel. When someone breaks your heart, it’s natural to wish you never met them, even if that person made you unbelievably happy for a precious, ephemeral period. But as Jim Carrey learns as he races through his memories of girlfriend Kate Winslet as they’re being erased, the manic rush and spiritual satisfaction of falling in love really is worth all the screaming matches and broken promises to come.
29. Billy The Kid (2007)
Every teenager feels like an outsider and a misfit, but those feelings are especially acute for Billy Price, the unforgettable 15-year-old hero of Jennifer Venditti’s bittersweet documentary exploration of the joy and crushing sadness of adolescence. Price has Asperger’s Syndrome, and his self-censoring apparatus is perennially on the fritz. He’s emotionally transparent in ways that are achingly poignant, even though they make his life more difficult. When Price becomes infatuated with a lazy-eyed girl behind the counter at a diner and she returns his stumbling, awkward advances, it looks like two misfits have finally found their perfectly imperfect soulmates, but heartbreak inevitably rears its ugly, ubiquitous head. “These years of loneliness have been murder,” Price blurts to amused onlookers, while still in the early stages of a relationship soon to sour. Even the happiest of Valentine’s Day lovebirds should be able to feel his pain.