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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.”


‘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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