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?