Narrowing down the greatest love stories, of any era, may very well be a fool’s errand. After all, practically every movie has a romantic subplot of one kind or another. It doesn’t matter if it’s a horror movie, an action movie, a biopic or a conventional rom-com; it seems like Hollywood doesn’t even know how to tell a story that doesn’t have a little love in it.
That means there’s a lot of competition for the best romantic movies of the 21st century. Whittling the list down to 25 was an agonizing process, like assembling a puzzle that came with way too many pieces. No matter how we assembled it something noteworthy got left out.
So before we get started, let’s offer up our sincerest apologies to the celebrated Gosling Triad; The Notebook, Crazy Stupid Love, and La La Land just barely missed the cut. The same goes for feel-good Disney flicks like Enchanted and WALL-E, superhero blockbusters like Wonder Woman and Spider-Man 2, and Oscar-winners like The Shape of Water and Lost in Translation. It seems like The Fault in Our Stars had just a few too many faults. And we sincerely hope we haven’t offended too many vampires by omitting both Only Lovers Left Alive or The Twilight Saga.
But what remains is, we feel, a rich assortment of romances from a variety of perspectives. Each one of these films will make you swoon, laugh or cry, and probably a combination of all three. If hard-pressed, yes, we think these are the best romance movies of the 21st century (so far).
Crouching Tiger, Hidden Dragon (2000)
Ang Lee’s Crouching Tiger, Hidden Dragon isn’t, as many films are, an action movie with a love story in it. It’s a love story with an action movie in it. What’s more, it’s one hell of a love story, and one hell of an amazing action movie. Michelle Yeoh and Chow Yun-fat star as martial artists who are in love but, through a stroke of fate, cannot allow themselves to be together. When they encounter a young martial artist, played by Zhang Ziyi, who refuses to abide by the rules that kept them apart, it sparks a heated conflict with lots and lots and LOTS of amazing sword fights.
Crouching Tiger, Hidden Dragon plays like a Merchant Ivory film, the kind where everybody holds their emotions back except for young people who, inevitably, create chaos by following their hearts. That those emotions are unleashed in astounding fight choreography by the legendary Yuen Wo Ping only elevates Lee’s film further. It’s a glorious ballet of love and war.
In the Mood for Love (2000)
It’s a cliché to use the word “aching” when describing a forbidden romance, but there’s no other way to adequately describe Wong Kar-wai’s masterpiece. In the Mood for Love stars Maggie Cheung and Tony Leung as people who discover that their spouses are having an affair. Over time, they grow closer and closer, and have to decide whether to let themselves fall in love as well.
In the Mood for Love takes place in a conservative era, where any relationship our protagonists have will draw scrutiny, and even condemnation. Being together would ruin their happiness. Being apart would be just as miserable. And so they ache, in a world gorgeously photographed to emphasize the power of their connection and the depths that separate them. Cheung and Leung are astounding, and few romances before or since have captured such a profound sense of longing.
Love & Basketball (2000)
Gina Prince-Bythewood’s directorial debut is more gloriously assured than the films of many industry veterans and remains one of the high water marks for romance movies over the last 20 years. Sanaa Lathan and Omar Epps star as Quincy and Monica, next-door neighbors since childhood who both dream of playing professional basketball. Over the course of their lives, they fall in and out of love, they get swept up in their ambitions and their family struggles, and eventually, they always find their way back to each other.
Love & Basketball never plays like a romance built on contrivance, or manufactured melodrama. It’s full of thoughtfully drawn, rich characters who attract and repel each other naturally, making good and bad choices, and never once ringing false. Lathan and Epps feel just right together; their chemistry is phenomenal throughout, whether they’re on or off the court. Gina Prince-Bythewood’s film never rings a false note.
Lots of romantic movies aim for “quirky” and wind up somewhere in the vicinity of “cloying” by accident. Not so with Jean-Pierre Jeunet’s charmingly weird Amélie, starring Audrey Toutou as a seemingly timid waitress who has a hidden streak of wild imagination. She gets it into her head to improve the lives of everybody around her, and she insists on doing it in whimsical ways like sending their garden gnomes on holiday without them, or tricking her friends into delightful romances.
Along the way she winds up finding true love herself, and it’s easy to imagine why. Jeunet’s film is pure love itself, a passionate ode to eccentricity, taking place in a cinematic realm where the kooky can thrive. Toutou captures our imaginations through her impish fascination with the people around her, and through her eyes, we appreciate all the wonders of the world.
Bridget Jones’s Diary (2001)
There were a couple of great adaptations of Jane Austen’s “Pride and Prejudice” in the early 2000s, but it’s this charming modern update that stands out the most. Bridget Jones’s Diary stars Renée Zellweger stars as Bridget, a woman caught in a love triangle between the dashing Daniel, played by Hugh Grant, and the seemingly disinterested Mr. Darcy, played by Colin Firth (who, in a bit of stunt casting, famously played Mr. Darcy in a straightforward Pride and Prejudice adaptation six years prior).
It’s Zellweger’s film – she earned an Academy Award nomination for her performance – but director Sharon Maguire has wonderfully furnished it for her. Bridget Jones’s Diary brings all the smoldering romance and biting commentary of Austen’s novel into the modern-day, finding the tale just as relevant as ever and contemporary romantic expectations just as rife for cunning commentary as those of the 19th century.
Not everybody loves each other the same way, and yet few romantic movies seem genuinely interested in truly exploring a lifestyle of sexual kink. At least we have Steven Shainberg’s Secretary. Maggie Gyllenhaal stars as a young woman who discovers, through an unexpected BDSM relationship with her new boss, that she’s a submissive who yearns for just the right dom. James Spader plays her new lover, but even he doesn’t seem wholly comfortable with who he is and what he really wants.
Secretary is an unusual film about people with very specific needs who find each other. Their desires may be specific but their fantasy is universal: they’re looking for someone who loves them for who they are, who can provide what they need, and with whom they can be mutually happy. That’s a dream that should not merely be reserved for the sensually milquetoast. The kinky deserve true love too, and Secretary is that rare love story that respects that everyone has unique needs, and tells a lovely story that suggests there’s someone out there for everybody.
Love Actually (2003)
Richard Curtis’s Love Actually seemed to come and go, and then come back again as a perennial yuletide classic. It’s easy to see why Love Actually didn’t find an audience right away: it’s astoundingly schmaltzy. It’s also easy to see why the film eventually became a holiday cult favorite: it’s astoundingly schmaltzy.
Love Actually tells a variety of short romantic stories, loosely connected, if only by geography. People fall in love, people fall out of love, people make hit Christmas music. Each story is pretty thin on its own but Curtis’s film intercuts between them so sharply that the film practically becomes a deadly weapon. If you can’t stand one tale, another is bound to charm you. And if you merely like them all, as a whole they take on genuine grandeur. (And if you don’t like any of these tales, you may very well be a Grinch.)
Before Sunset (2004)
Nine years after making waves with his enchanting love story Before Sunrise, Richard Linklater returned with his stars Julie Delpy and Ethan Hawke to find out what Celine and Jesse have been up to. After spending one perfect night together, meeting and falling in love, and then saying goodbye, they reunite for a few short hours. Did their love story continue when we weren’t looking? And if not, is there any chance to rekindle their romance, or will they write off the whole beautiful first film as a young fling?
Before Sunset somehow manages to feel fleet-footed and severe at the same time. Delpy and Hawke have the kind of on-camera connection that few actors could ever dream of, but they have such a short amount of time together, and nearly a whole decade of each other’s questions to answer. Linklater’s film reminds us why we loved them and, perhaps, why they should love each other, but the answer to what happens next is reserved only for the very end, which may very well be the best ending to any romantic tale this century. Heck, maybe even the last century too.
Brokeback Mountain (2005)
Ang Lee’s powerful Oscar-winning romance Brokeback Mountain is one of the most resonant modern westerns. Heath Ledger and Jake Gyllenhaal star as mid-20th century cowboys who fall in love on the job and then go their separate ways, each settling for heterosexual marriages that bring them social safety but no happiness. They reconnect and rekindle their romance but each clandestine meeting comes with the danger of discovery.
Told with elegiac restraint, adding even more significance to a love affair where little is said, Brokeback Mountain relies on an overwhelming ensemble of performances. Ledger’s quiet dignity and Gyllenhaal’s energy seem to capture lightning, and Michelle Williams and Anne Hathaway both steal key moments as the women who come to realize they married men who always wanted something more.
The Holiday (2006)
The films of Nancy Meyers tend to portray the lives of the bourgeoisie in fairy tale terms, and never was it more successful than in The Holiday. Cameron Diaz and Kate Winslet play women who, searching for a change of pace after failed relationships, decide to switch houses. Winslet ventures into Southern California, moving into a palatial mansion next to a charming Golden Age of Hollywood screenwriter, and starts to fall for a film composter played by a pitch-perfect Jack Black. Meanwhile, Diaz moves into Winslet’s cozy, super expensive cottage and romances the dapper Jude Law, who turns out to be Winslet’s brother.
The perfection on display in The Holiday would be suspect if the title didn’t perfectly frame it: this is an exceptional vacation from everyday life. The problems are emotionally intense but solvable, and the characters have the freedom to worry about their foibles without serious concerns to distract them; stupid little things like bills, for example. And the whole cast is just so unimaginably delightful that you cannot begrudge them this happiness. You can only revel in it, fall a little in love, and then begrudgingly go back to real life. Like those stupid bills.
John Carney is famous the world over for making passionate, character-driven films full of awesome music, like Begin Again and Sing Street. But his masterpiece is still this infectiously low-key, lovely romance. Once stars Glen Hansard as a busker in Ireland, working in his father’s vacuum cleaner repair shop when he isn’t singing songs about his latest breakup in the street. When his music catches the ear of a Czech immigrant played by Markéta Irglová, they strike up a friendship based on mutual, musical appreciation.
And naturally, they fall in love, but sadly, there’s nothing they can do about that. All they can do is scrape together whatever money they can, write some songs, and cut a record. Carney understands that the real thrill of watching their tale play out lies in watching the art his characters make, not in the contrived machinations of a story pushing them this way and that. There’s an intoxicating realness to Once, revelry in the power of music to connect with other human beings, that shines through and makes it truly special.
They Came Together (2014)
There’s a specific brand of romantic comedy that doesn’t get made much anymore, but was a box office powerhouse in the 1990s. Fans of films like You’ve Got Mail, While You Were Sleeping and Notting Hill can recognize every gloriously hackneyed storytelling convention from a mile away, and if they have any sense of humor whatsoever about that, David Wain’s brilliant parody They Came Together is just about the perfect comedy.
Paul Rudd and Amy Poehler star as people who are so different they couldn’t possibly get together, who discover they have something in common when they realize they share a unique passion for “fiction books.” But will their love survive phony plot points, twee digressions, and wacky supporting cast members? Will it almost be like New York City is a character in the film? You know the answers, but that just makes it more hilarious to Wain and his wacky cast go through those motions in the weirdest, most self-aware ways imaginable.
And yet, They Came Together doesn’t feel vicious or condescending. The only way you’d even get all these jokes at the romantic comedy genre’s expense is if you genuinely loved the romantic comedy genre. Wain’s film is a wonderful comedy roast of the genre, giving it endless guff for its foibles, but hugging it out when the act is done.
Patricia Highsmith’s groundbreaking novel The Price of Salt was transformed into one of the most stunning romances in decades. Carol, directed and adapted by Todd Haynes, stars Rooney Mara as a clerk at a department store who meets, quite by chance, a rich socialite played by Cate Blanchett. Their relationship grows into a romance but social mores and the effect a scandal could have on a divorce threatens to tear them apart.
Few films are as stunningly photographed and elegantly designed as Carol. It’s a film that understands the effect of affect, where style becomes substance and substance is, itself, a certain manner of style. Haynes’ film cuts through its own aesthetic and sinks into the difficult decisions and stymied inner lives of its heroines. Their story is profound and beautiful, and the harsh realities of conventional and conservative society can only hold them back for so long.
Sleeping With Other People (2015)
There haven’t been a lot of great, naughty rom-coms in the 21st century, but Leslye Headland’s Sleeping With Other People would have stood out even if the competition were stiff. Jason Sudeikis and Alison Brie star as Jake and Lainey, two sexually overactive people who realize that their drives are ruining their lives. So they vow not to sleep with each other no matter how aroused they get. And they get very, very aroused.
Sudeikis and Brie keep the sexual chemistry at a low boil for all of Sleeping With Other People, and yes, we know where this is going and yes, it’s only a matter of time. But Headland’s spry screenplay and winning sense of humor work wonders, and she constantly mines the strong set-up and delightful characters for laugh-out-loud jokes and genuine romance.
Quite a lot of superhero movies have a love story to tell amidst all the costumed crimefighting, but for some reason it’s the one about a mass murderer who knows he’s in a movie that stands out. Deadpool stars Ryan Reynolds as a mercenary who finds the love of his life, Vanessa (Morena Baccarin), a hilarious and sensitive and intelligent and sensual partner who makes his life worth living. So when he finds out he’s dying of cancer he flees to spare her the horror of watching him die, and he runs headlong into a secret government program that tortures him ruthlessly, in the hopes it will cure him and restore his life.
It is, of course, a devil’s bargain, and Deadpool emerges with superhuman healing powers but permanently marred skin, which only makes him more self-conscious about reuniting with his partner after so much of their relationship was physical. And at that point yes, there’s lots of action and violence and potty humor, but Deadpool would merely be a lark without a genuine, human story to ground it. And the story of a man whose insecurity nearly robs him of the relationship he wants, who ignores what his lover is telling him because he’s terrified that it’s not what she really needs, is far more thoughtful, accessible, and real than most of the other films in its genre.
Southside With You (2016)
Richard Tanne’s intimate and absorbing Southside With You would be one of the best romantic movies of the decade if its subjects were fictional. That it’s also based on the true story of Barack Obama and Michelle Robinson’s first date is but another intriguing selling point. Southside With You follows Robinson, played by Tika Sumpter, as a young lawyer and Obama’s supervisor, who agrees to meet the summer associate for a community meeting. She hesitantly agrees to meet up earlier, but has no interest in an office romance.
Southside With You takes place over the course of the afternoon and early evening as these two individuals with powerful personalities share their thoughts on life, on politics, on race, and find a connection building between them. It’s not love at first sight, and it’s not a passionate love affair. It’s two complex individuals with big ideas and serious dreams coming to realize, for the first time, that they could be more. Tanne’s film may not be able to fully escape a sense of mythologizing, and yet few romance movies in recent memory approach love and dating with the same confident maturity, regardless of the context.
The Big Sick (2017)
Kumail Nanjiani and Emily V. Gordon wrote the screenplay for this observant and extremely funny romance, which is based on their own true story. Nanjiani plays a version of himself, a standup comedian who falls in love with a woman named Emily (Zoe Kazan) who, suddenly, falls into a coma due to a mysterious ailment. While she’s sick, he strikes up an uneasy friendship with her parents, played by Holly Hunter and Ray Romano.
The Big Sick isn’t afraid to show Kumail in a pretty harsh light, when he deserves it, and it’s that brutal honesty that makes this otherwise humorous film so richly emotional. It’s the kind of movie that uncorks your tear ducts, sometimes without warning, and yet it leaves you feeling nourished and warm and fulfilled.
Call Me By Your Name (2017)
A teenager finds his first true love, and it’s fleeting, in Luca Guadagnino’s sumptuous romance Call Me By Your Name. Timothée Chalamet stars as Elio, a young man whose father enlists the dashing Oliver, played by Armie Hammer, as his research assistant for the summer. It’s a summer of longing glances and will-they-or-won’t-they suspense, until it finally consummates in a passionate love affair they won’t soon forget, even if fate has other plans for their future.
Call Me By Your Name is a love letter to practically everything. The film’s glorious Italian villa locale is the ideal setting for a romantic drama, the music is intoxicating, and the cast has never been more ethereally captured on camera.
A Star is Born (2018)
By the time Bradley Cooper got around to remaking A Star is Born, it was already the fourth adaptation of the story. (Possibly even the fifth, you consider that the original 1937 film is suspiciously similar to 1932’s What Price Hollywood?) Once again it’s the story of an aspiring artist taken under the wing of an alcoholic has-been, who uses his clout to lift her to stardom, only to fall in love with him as he sinks into alcoholism and scandal. And once again, the danged story really works.
A Star is Born is a love letter to the entertainment industry just as much as it is a vicious screed against it, portraying the whole environment as an exploitative den of selfish behavior and lifelong human sacrifice. Cooper’s rendition, in which he co-stars along with a stellar Lady Gaga, keeps that contrast front and center, but never loses track of the fact that if the love story doesn’t work, nothing does. Cooper and Gaga have four-alarm fire chemistry with each other, and the Oscar-winning music that accompanies their rise and fall tells their story beautifully too.
Crazy Rich Asians (2018)
Jon M. Chu’s charming and funny adaptation of Kevin Kwan’s novel stars Constance Wu as Rachel, a Chinese-American professor who travels to meet her boyfriend’s family in Singapore, only to discover they’re astonishingly wealthy. And so begins a familiar tale of class conflict, as a young woman from a working-class upbringing suddenly gets immersed in fabulous privilege and glorious excess. Not to mention the constant leers of disapproval.
Crazy Rich Asians is an old-fashioned throwback to Hollywood romance movies, larger than life, riddled with memorable character actors, and adherent to a feel-good formula. But it’s more than that, it’s a distinctive and transportive romantic comedy with performances that would elevate any material, and an appreciation for a culture that mainstream Hollywood rarely even attempts to explore. It’s one of the best rom-coms of the last 20 years.
An unfortunate DC trend, revisited.
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