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50 Greatest Romantic Comedies of All Time

From ’30s screwballs to 21st-century meet-cutes, Rock and Doris to Hanks and Ryan — our picks for the best rom-coms ever

Say Anything, Moonstruck, When Harry Met Sally

Moviestore Collection/Shutterstock (2);Castle Rock/Nelson/Columbia/Kobal/Shutterstock

Take two people. Find a way to pair them up — maybe they’re on a cross-country trip together, maybe they both work in the same office, maybe they’re rivals in the same industry. Better yet, they might even be two parts of a love triangle. The scenarios are endless. Now throw some obstacles in their way, from geography to class issues to vengeful exs and/or brand new beaus. Or the conflict could be as easy as the fact that they just don’t like each other — in fact, they despise the other person. Then, after a lot of comic shenanigans and trying circumstances, they realize that they’re really meant for each other. Cupid’s arrows hit their marks. Roll credits.

It sounds simple, right? But to make a great romantic comedy — like, a really classic, stand-the-test-of-time one — requires skill, chops, expert timing, the right chemistry among your leads and the ability to pull heartstrings and hit funny bones at the same time. It’s a tougher balancing act than most folks would care to admit, and all the more impressive when filmmakers and actors actually do pull it off.

And the romantic comedies we’ve singled out here aren’t just impressive — they are, in our humble opinions, the cream of the genre crop, the best of the best. In honor of Valentine’s Day, a.k.a. the holiday where everyone craves both rom-com viewing time and argument-starting ranked lists, we present our choices for the 50 best rom-coms of all time. From ’30s screwballs to 21st century meet-cutes, Rock and Doris to Tom and Meg, these are the ones that had us at “hello.”


‘Annie Hall’ (1977)

Woody Allen is so central to his films’ appeal — which is why the dark cloud hovering over the writer-director-star makes it difficult now to fully access what is so poignant, hilarious, hip and thoughtful about this unlikely Best Picture-winner that radically modernized the romantic comedy. This story of a neurotic comic (Allen) and an aspiring singer (Diane Keaton) isn’t just about how people fall in love — it’s about how they fall out of love, drift apart, realize that their once-hot passion will eventually dissolve into an enduring, distant fondness (if they’re lucky). Annie Hall endures as one of the most honest portraits of attraction’s ebb and flow, embodied in Keaton’s unimpeachable performance as a budding artist who eventually learns she doesn’t need an insecure man’s approval to love herself. TG

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‘Groundhog Day’ (1993)

The existential quest for self-betterment has never been more hilariously, nor more movingly, teased out than in this Harold Ramis classic, which could be subtitled Phil Connors in the Bardo. As Bill Murray’s grouchy weatherman is forced to endlessly relive the same frigid February day in the limbo known as Punxsutawney, PA, he moves from irritation to nihilism to depression to, finally, the earnest pursuit of true love. Amid our man’s meanderings on that infinite winter’s day, the true pleasure of Groundhog Day is watching him fall for — and then work to make himself worthy of — his producer Rita (Andie MacDowell). What’s more romantic than a guy learning to carve ice sculptures for you? JS

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‘Bull Durham’ (1988)

The thing about baseball is, when you’re evaluating a fastball pitcher … wait, come back! Bull Durham was a breakthrough in the Eighties — a sports movie that doubled as a date flick. Susan Sarandon stars as an intellectual North Carolina baseball fan with a thing for handsome minor-league prospects. She spends the movie juggling a couple of conspicuously younger suitors: catcher Kevin Costner and pitcher Tim Robbins. It finally made a star out of Sarandon, who’d been kicking around Hollywood for a couple of decades without getting her chance to shine as a wise-cracking feminist leading woman. And Costner got a career-making speech in praise of “long, slow, deep, soft, wet kisses that last three days.” RS

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‘The Apartment’ (1960)

As C.C. Baxter, the most put-upon of all his put-upon characters, Jack Lemmon plays a white-collar drone so ineffectual that he loans out his apartment for his boss’s extramarital dalliances, pining for some up-the-corporate-ladder payout down the line. Which is why he shares a kinship with Shirley MacLaine’s elevator operator, who’s also getting strung along by a two-timing executive. But it’s the contrast between his mania and her melancholy that holds Billy Wilder’s brilliant, winsome office comedy in balance — as if they’re tugging each other in the right direction. Just watch how Lemmon clowns around in a “junior executive” bowler hat and takes MacLaine’s holiday blues away. Out of miserable circumstances, the two lonelyhearts bond in their humor, resilience and mutual insistence on dignity. It’s a match made in heaven, one floor at a time. ST

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‘Say Anything’ (1989)

One of the most tender teen comedies in the canon: Lloyd Dobler (John Cusack) set the stage for high-school boys to be more than a heap of hormones. Seriously, who could have played this sweet, boom box-toting antidote to dude-bros, i.e. the knucklheads hanging out at the Gas ‘n’ Sip pontificating about the opposite sex? Described as “basic” by brainy, beautiful Diane Court (Ione Skye), our underachieving hero nonetheless wins her heart … only to get his broken. Both Skye and Cusack bring such raw, physical emotion to their performances that the story easily evolves beyond strict rom-com. It’s still funny — just yell “You. Must. CHILL!” in your best Dobler voice and try not laugh. But ultimately, it’s their young love that’s as satisfying as the ding after a plane takes flight. PR

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‘Moonstruck’ (1987)

Casting “crazy” Nicolas Cage as a romantic lead may seem absolutely loony. But that’s partially why Moonstruck still feels so charming: It’s a mature love story that explains why it’s sometimes right to fall for Mr. Wrong. Cher is Loretta Castorini, a cautious Italian-American widow all set to get remarried to a bland fella. Then guess who has her heart stolen by his surly one-handed sibling, played by you-know-who? And who knew these actors would fit so well together? It’s a movie that has both the ring of seen-it-all truth and the atmosphere of a fairy tale — like a Dean Martin song come to life. “Snap out of it!” NM

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‘Clueless’ (1995)

Writer-director Amy Heckerling didn’t set out to reinvent Jane Austen — Clueless was supposed to be about the adorable narcissism of Beverly Hills teens. Then she realized that the rest of America might not find these super-rich kiddos so cute, so she borrowed the moralistic plot of Austen’s 1815 novel Emma. And in a second stroke of genius, she cast the preternaturally cheery Alicia Silverstone as her meddling heroine, who plays matchmaker and makeover expert for her friends, yet can’t spot her own flaws — until she finds someone to love her, that is. (Hi there, Paul Rudd!) The result … well, you know what the result is. It’s a modern teen-movie classic, a Hall-of-Fame romantic comedy and the film most responsible for adding “As if!” to the lexicon. And this story’s truly timeless, even in a 1995 world filled with enormous cell phones and spontaneous appearances by the Mighty Mighty Bosstones. NM

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‘His Girl Friday’ (1940)

In this corner: Cary Grant, the world’s most dashing newspaper editor. In that corner: Rosalind Russell, his ace reporter, who also happens to be his ex-wife. In a few days, she’s getting married to bland ol’ Ralph Bellamy (right!) and leaving the news racket forever — but first, these two have one last big story to break. Howard Hawks adapted the play The Front Page, turning the reporter into a woman, with Russell yelling endearments like “Now get this, you double-crossing chimpanzee!” It remains one of the speediest comedies ever made — Hawks wrote overlapping dialogue to better mimic the way people talk, then asked his actors to read the lines twice as fast as usual. In the days before Robert Altman or Veep, no movie crammed in so many rapid-fire insults per minute. RS

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‘Broadcast News’ (1987)

Why does love got to be so sad? That question haunts James L. Brooks’ very funny, incredibly bittersweet look at the vagaries of romance and TV journalism. The writer-director crafted what he later called a film about “three people who lost their last shot at intimacy,” presenting a romantic triangle consisting of a neurotic reporter (Albert Brooks), the news producer he secretly loves (Holly Hunter) and the shallow, handsome broadcaster she should despise but instead finds charming (William Hurt). Personal and professional ethics are at the heart of Broadcast News, but this is also a wise film about the impossibility of juggling love and career. Its ending may not technically be “happy,” but it’s piercingly true. And you simply can’t beat a line like “Wouldn’t this be a great world if insecurity and desperation made us more attractive?” TG

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‘The Philadelphia Story’ (1940)

“Either I’m gonna sock you or you’re gonna sock me!” “Shall we toss a coin?!” The Philadelphia Story’s verbal pyrotechnics are merely part of the brilliance of this 1940 Oscar winner, in which dejected ex-husband C.K. Dexter Haven (Cary Grant) conspires with journalist Mike Connor (Jimmy Stewart) to crash the glitzy wedding of Haven’s former wife Tracy Samantha Lord (Katharine Hepburn). Fans love the biting back-and-forth dialogue among this trio of combatants — a scenario that only gets more complicated once she starts falling for both men. But beyond the witty repartee and impossibly beautiful actors, director George Cukor skillfully underlines the poignancy of people using love as a quick fix for deeper insecurities and gnawing dissatisfactions. All that, plus a pitch-perfect urbane tone, airtight plotting and the best flirty effervescence the Golden Age of Hollywood could buy. Pure rom-com bliss. TG

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‘When Harry Met Sally’ (1989)

The Attraction Theory. The bookstore encounter. The New Year’s Eve admission of love. The vignettes of older couples recounting their relationship stories. “You made a woman meow?!” The split screen phone call involving Carrie Fisher and Bruno Kirby’s best friends. The deli scene — dear god, that deli scene. Chances are good that when you hear the phrase “rom-com,” Rob Reiner’s movie — about two longtime acquaintances who finally realize the only people that are truly right for them is each other — was the first title you thought of. Yes, it owes a good deal to Annie Hall in its tenor and tone, but what Billy Crystal and Meg Ryan do with these roles is sui generis; it’s a one-of-a-kind alchemy. And anyone who does not think Nora Ephron was as great a screenwriter as she was an essayist simply isn’t paying attention. It is the one rom-com to rule them all, a perfect distillation of the form. We’ll always have what they’re having. DF

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