With Valentine’s Day fast approaching, today we’re counting down the very best romantic movies — from beloved meet-cutes that feel as cozy as being wrapped up in a warm blanket to old-fashioned tearjerkers that will shatter your heart into a million pieces.
From the first awkward stirrings of attraction and the giddy thrills of a fleeting encounter to the crushing lows of a missed connection, the following list represents just the tip of the iceberg in more than a century’s worth of swoon-worthy love stories that have charmed audiences and made us sob uncontrollably. Unfortunately, we couldn’t find room for time-honored classics like “The Clock”, “The Apartment”, “Moonstruck”, “The Lady Eve”, “City Lights”, “An Affair to Remember”, “It Happened One Night”, or “Comrades: Almost a Love Story”, while many other tales of forbidden romance (“In the Mood for Love”, “The Age of Innocence”, “Brokeback Mountain”, “All That Heaven Allows”, and “Pride & Prejudice”) could just as easily have found their way on here and obviously deserve your attention as well.
Our lineup below, listed in chronological order, offers a collection of movies that will tug at your heartstrings and are well worth revisiting time and time again.
1. History is Made at Night (1937)
Forget Leo DiCaprio and Kate Winslet in “Titanic” — If you’re looking for the ultimate Hollywood romantic melodrama set against the backdrop of a tragic maritime disaster involving an iceberg, do yourself a favor and add this unsung masterpiece by Frank Borzage to your streaming queue.
In this buried treasure from Hollywood’s golden age ripe for reappraisal and newly restored by Criterion, the always-reliable Jean Arthur is an understated powerhouse as a wealthy American socialite caught in a tangled web of misunderstandings and messy divorce battles and torn between her possessive ex-husband and a sophisticated Parisian head waiter (Charles Boyer).
Sure, “History is Made at Night” may be syrupy enough to give viewers a sugar rush on their first go-round. But dig a little deeper and you’ll see there’s also a bit of something for everyone to enjoy: heartfelt performances, razor-sharp dialogue, Sirkian melodrama, pointed social commentary, screwball hijinks, grand setpieces, and a showstopping finale that puts James Cameron’s $2 billion tentpole to shame. Just make sure to have a box of tissues nearby.
2. Casablanca (1942)
You likely don’t need a reminder that “Casablanca” is a pretty fantastic romantic film. However, after being chewed up incessantly, buried under critical acclaim, and spoofed across all media for 83 years now, it’s easy to forget that during production, nobody involved including director Michael Curtiz realized they were making one of the best tearjerkers of Hollywood’s golden age as well as one of the most enduring Best Picture winners of all time.
We all love to quote lines of the dialogue by heart — “Here’s looking at you, kid”, “We’ll always have Paris,” and “Louis, I think this is the beginning of a beautiful friendship” have all entered the cultural lexicon at this point. And while its underlying theme of personal sacrifice for the greater good in the face of unfathomable evil obviously continues to strike a chord, what truly keeps us coming back is the irresistible megawatt star pairing of Humphrey Bogart and Ingrid Bergman as Rick and Ilsa — a pair of doomed old flames helplessly swept aside by the tides of history who reconnect behind enemy lines in North Africa during WWII. Fellas, they don’t make ’em like they used to.
3. Brief Encounter (1945)
Swooning romantic yearning builds to a fever pitch in this gorgeously-shot, post-war tale of mismatched lovers concerning two ordinary people — a married doctor (Trevor Howard) and a suburban housewife (Celia Johnson) — who earnestly fall head over heels for one-another after meeting at a railway station.
When one thinks of the great David Lean, grand, sweeping period epics with thousands of extras, colossal budgets, and an even bigger runtime instinctively spring to mind — not so much a hushed, 86-minute weepie. But despite scaling things down and working on a considerably smaller canvas than usual, the “Lawrence of Arabia” British director is just as effective and stirs up an ocean of emotions by making every little line of dialogue, gesture, and subtle glance count — though it is the things that are ultimately left unsaid that haunt the viewer the most.
An octogenarian black-and-white stage adaptation that consists almost entirely of quiet, intimate conversations between two grown adults can be a hard sell to watch for Valentine’s Day. But if you’re looking for a title that will tug at your heartstrings and leave you and your special someone in a puddle of tears, “Brief Encounter” is just the ticket.
4. Roman Holiday (1953)
Even by standard rom-com standards, the palpable chemistry between Audrey Hepburn and Gregory Peck here is as good as it gets and virtually impossible to resist. The A-list Hollywood coupling crack and sizzle together and set the screen aflame in this breezy fairy tale directed by William Wyler about a runaway European princess, Ann, who escapes from her dreary royal duties during a diplomatic visit to Rome only to run into a streetwise American reporter, Joe Bradley.
Part Cinderella story, part Italian travelogue, you simply couldn’t ask for a finer tonic for the soul to whisk you away, lift your spirits, and put you in a good mood when you’re feeling down than watching these two mismatched love birds gleefully riding around on a Vespa scooter through the streets of the Eternal City, doing some sightseeing, touring the Colosseum, and even attending a dance on a boat. The outcome is never truly in question — early on, it’s clear Joe is too smitten with Ann to betray her trust for the sake of getting the big scoop — but the bittersweet ending hits you like a ton of bricks nonetheless.
5. The Umbrellas of Cherbourg (1964)
At a critical juncture in time when the big-budget musicals Hollywood’s studio system was dishing out grew increasingly bloated and stale, all it took was the most hopelessly romantic director in all of France trying to get his honest-to-goodness homage to old MGM musicals off the ground to jolt new life into the genre and steer it back on course.
“My Fair Lady” may have taken home the Oscar, but of all 1964 musicals, time has been most kind to this one by Jacques Demy, a candy-colored and immaculately staged emotional rollercoaster that recounts the on-again, off-again relationship between bright-eyed teen shopgirl Geneviève (a radiant Catherine Deneuve in a star-making turn) and a local garage mechanic called Guy (Nino Castelnuovo).
The sparks fly but, alas, fate had other plans. Before long, Guy is unexpectedly called up for military service in the Algerian War, leaving the newly pregnant Geneviève in complete disarray. With no other choice, she gives in to his mother’s demands and ends up settling for a Parisian upper-class suitor instead. The musical numbers and dazzling choreography will take your breath away, and if watching these star-crossed lovers reunite years later at a desolate gas station doesn’t make you well up inside, you must have a heart of steel.
6. When Harry Met Sally (1989)
Hardly a controversial pick, the meet cute to end all meet cutes that launched Meg Ryan and Billy Crystal’s careers into the stratosphere, has charmed audiences since the late ’80s, and continues to sweep us off our feet every fall grapples with a simple but very pertinent question: Can men and women just be friends without sex getting in the way?
At the center of it all is the perfectly matched and irresistibly charming screen couple of Meg Ryan and Billy Crystal, who give it much thought during a long road trip from Chicago to New York and then 12 years down the line in a witty battle-of-the-sexes that sees them get together and fall out many times over.
If Woody Allen deserves credit for essentially laying out the blueprint for the modern romcom in 1977 with “Annie Hall”, Rob Reiner’s box-office smash hit — penned by genre specialist Nora Ephron of “Sleepless in Seattle” fame — basically perfected its tried-and-true formula and brought it up to speed for the edgy 1990s. Come for the iconic fake orgasm scene, and stay for the real climax in one of the most memorable and life-affirming endings of all time.
7. Chungking Express (1994)
There is a reason why the name of Wong Kar-wai has become synonymous with romantic longing. Few directors in cinema history have ever captured the pang of heartache and giddy rush of a fleeting encounter with as much rawness, candor, and sense of flair. The bustling, neon-soaked streets of pre-handover Hong Kong often provided the vibrant backdrop to his melancholy love tales, a fitting choice that reflects the bitter irony of modern city life — where people live in close proximity yet remain profoundly lonely more often than not.
Quentin Tarantino once claimed that he doesn’t know anyone who’s seen “Chungking Express” without developing a crush on Faye Wong — and frankly, he was onto something. In the breakout role that introduced the whimsical charms of the former Canto-pop star-turned-actress to Western audiences, Faye plays a quirky oddball who spends her shifts at a takeout food stand daydreaming about moving to California while listening to The Mamas and The Papas on repeat — that is when she’s not secretly sneaking into the apartment of a melancholic cop (Tony Leung). Trust me, it’s adorable and not at all creepy if you actually sit down and watch the film!
At its core, this is a movie about how going through a breakup is always hard and painful — but a little less so if you’re lucky enough to cross paths with a kindred spirit that you can lean on. Prepare to have California Dreamin’ stuck in your head for days.
8. Before Sunrise (1995)
What if you decided to interact with that attractive random stranger you once brushed past, locked eyes with, and perhaps even imagined a lifetime together while on the bus, train, or subway? In a nutshell, Richard Linklater’s masterpiece essentially plays out that daydreaming fantasy for real, following two idealistic twentysomethings — a French student and an American tourist — who, after a chance encounter on a train, spend one fateful day together strolling through the streets of Vienna.
Céline (Julie Delpy) and Jesse (Ethan Hawke) are obviously fictional characters, but their conversations are so vivid and authentic that they never once come across as any less than real people you’ve known for years, so of course, it hits you right in the gut to see them forced to part ways at the end. Both sequels, though nowhere near as romantic, arguably make “Sunrise” all the more rewarding to revisit. But the field was too tight to make room for Richard Linklater’s entire trilogy, so we’re making a bid for the one that got the ball rolling in the first place — a film that, after all, is a top-to-bottom, self-contained masterpiece in itself.
9. Punch-Drunk Love (2002)
Finding someone who accepts you just the way you are, warts and all, is a particularly powerful and empowering feeling, especially if you struggle with low self-esteem or don’t always feel comfortable in your own skin. It may not follow the rom-com playbook to a tee by any stretch, but “Punch-Drunk Love” deserves a place in this list precisely because it supports this notion better than any other Hollywood movie in the genre, and cleverly uses it as a jumping-off point for one of the most off-kilter yet invigorating love stories in recent memory.
In 2002, Adam Sandler didn’t have the highest batting average among his peers and was something of a common target among smug critics, but his credentials as a credible rom-com lead were solid as a rock by the time he was approached by Paul Thomas Anderson to play a mild-mannered toilet-plunger salesman called Barry. On paper, the fit didn’t seem obvious — PTA was a capital-A Auteur who was being hyped up as the heir apparent to Robert Altman and Martin Scorsese, while the former SNL star was racking up Razzie nominations at a faster clip than Sly Stallone.
Lo and behold, it turned out to be a match made in heaven, and “Punch-Drunk Love” finally gave Sandler the role he was born to play as a self-loathing, constantly belittled man who learns to love himself after inadvertently falling for a fellow introvert (Emily Watson). Just thinking about that Hawaii kiss scene is enough to reduce us to a sobbing mess.
10. Portrait of a Lady on Fire (2019)
If all lovers feel like they’re inventing something, this is especially true of Marianne (Noémie Merlant) and Héloïse (Adèle Haenel), two lonely women who find solace in each other and create a world all unto themselves after crossing paths on a remote island in Brittany. Marianne, a painter, has been commissioned to paint the wedding portrait of Héloïse, who’s set to be married off against her wishes to a wealthy nobleman from Milan. Thus begins a slow-burning battle of wills and intimate bond between artist and muse, the gazer and the gazed, that challenges the usual conventions of the standard prestige period drama to drive a stake through the heart of the oppressive patriarchal society of 18th-century France.
Having already attained modern-classic status (in fact, it even cracked the top 30 in the latest Sight & Sound poll) and wholly deserving of a place in the all-time pantheon of romantic movies, Celine Sciamma’s “Portrait of a Lady on Fire” is a lightning-in-a-bottle masterpiece that feels at once oddly specific and timelessly universal — a tale of forbidden love as old as time that reflects on the past but very much feels in conversation with our present. Frankly, who could’ve thought a simple callback to a page number could carry so much emotional weight?
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