The 10 Best Romantic Movies of All Time

tulipmovies June 28, 2020

The 10 Best Romantic Comedy Movies: The death of the romantic comedy has been greatly exaggerated. Yes, the genre has faltered in popularity since its 1990s heyday—but recent developments prove that audiences are still hungry as ever for banter, meet-cutes, and happy endings. This summer, Netflix has hit pay dirt by leaning hard on frothy comedies about pretty young things falling in love; this week, Crazy Rich Asians will storm theaters, putting a new sort of gloss on a tale as old as time.

Which got us thinking: what are the films that best exemplify this beloved but under-appreciated genre? After each member of Vanity Fair’s Hollywood team, including all three of our critics, came up with his or her own personal top 10 list, we crunched the numbers, noting which films appeared most frequently, and—after a few brief arguments about what constitutes a romantic comedy, and what does not—came up with the final tally. Though 25 movies ultimately made the list, 20 more were left off because they received only a single vote—films that ran the gamut from Obvious Child to White Christmas to Strictly Ballroom to Wall-E. The takeaway, perhaps, is that “romantic comedy” is an elastic designation, one that lies at least partly in the eye of the beholder—appropriate enough for a genre focused on love.

Our ultimate list is an eclectic mix, containing everything from black-and-white classics to, well, How to Lose a Guy in 10 Days. And while every single pick may not contain every element commonly associated with the romantic comedy, they all fit the American Film Institute’s broad definition of “a genre in which the development of a romance leads to comic situations.” Of course, they’re all funny, too.

1. When Harry Met Sally (1989)

When Harry Met Sally

It can be hard to find something new to say about Rob Reiner and Nora Ephron’s romantic classic, because it has topped lists and been so praised in the past. How it hits you in both the heart and the funny bone is just part of why this one works, putting together Meg Ryan and Billy Crystal’s initially unlikely lovers. There are the endlessly quotable exchanges, Carrie Fisher stealing scenes like she’s wearing a mask and a striped jumper and the sort of lasting impact that so many movies in the genre have failed to match before or since.

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2. Casablanca (1942)

Casablanca

Humphrey Bogart. Ingrid Bergman. One iconic gin joint. Set against the backdrop of World War II, the story of emotionally bruised bar owner Rick and the return of Ilsa, the old flame who left him emotionally distant, is univeraslly regarded as one of the all-time greats. Its central love story is bittersweet, with a sacrificial pay-off that only bolsters its emotional impact. When you’ve seen it once, you’ll be desperate to play it again.

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3. Brief Encounter (1945)

Brief Encounter

With its ‘a stable husband is better than a passionate lover’ message (hey, it was the 1940s), Brief Encounter is both achingly romantic and poignantly melancholic. Laura and Alec’s first grit-eyed conversation on the train platform is perhaps the original meet-cute, but the duo’s profound connection faces scrutiny from the social mores of the era. The end of the affair is enough to leave you with more than just a speck of dust in your eye.

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4. Four Weddings and a Funeral (1994)

Four Weddings and a Funeral

In one fell swoop Richard Curtis made the jump from Blackadder to the big-screen, propelled Hugh Grant and Mike Newell’s careers, and defined a whole new era of British rom-coms. Four Weddings and a Funeral delivers on the bittersweet promise of its title, balancing foul-mouthed dialogue with chocolate box London locales, all topped off with a rain-soaked feel-good finale.

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5. The Princess Bride (1987)

The Princess Bride

Rob Reiner’s cult classic flings sickly fairytale tropes off the Cliffs of Insanity on its way to happily ever after. The swashbuckling romance between Princess Buttercup and her faithful farmhand-turned-pirate Westley is so witty, feisty, and engaging that even 10 year-old boys don’t mind the kissing bit. Relationship goals: find a partner that you’d hurl yourself down the world’s longest hill for.

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6. True Romance (1993)

True Romance

That title’s not ironic — underneath the cocaine, the murders, and Gary Oldman’s dreadlocked Drexl, Tony Scott’s Tarantino-penned crime saga has a raw, beating heart in Christian Slater and Patricia Arquette’s ride-or-die lovers. The film that changed the meaning of ‘three little words’ from “I love you” to “you’re so cool… you’re so cool… you’re so cool…”

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7. Annie Hall (1977)

Annie Hall

How far Woody Allen’s private life can be extricated from his work is still an ongoing conversation, but viewed in a cultural vacuum (if such a thing is possible or even advisable), Annie Hall stands as one of the finest rom-coms ever made. Diane Keaton is the titular Annie, the laid-back lover of neurotic stand-up comic Alvy. The film avoids emotional grandstanding and instead focuses on the minuscule everyday moments that bring flashes of muted joy and disappointment on a daily basis, topped with fourth-wall-breaking gags and wry asides. It’s unlikely to win new fans, but hard to forget for those who have already seen it.

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8. Before Sunset (2004)

Before Sunset

Leave it to Richard Linklater to experiment with the format and find something new to say about how love evolves across the years. A follow-up to 1995’s Before Sunrise, it catches up with Ethan Hawke’s Jesse and Julie Delpy’s Celine nine years later for more walking, talking and romance. Written by the cast with their director, it feels like it emerged organically instead of being forced into existence. And it’s warm, witty and real when dealing with affairs of the heart, for good and ill.

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9. Jerry Maguire (1996)

Jerry Maguire

Cameron Crowe’s genre mash-up combines the pure joy of falling head over heels in love with the thrills of, erm, sports management deals. It’s more romantic than it sounds, delivering two of cinema’s greatest ever declarations of love within fifteen seconds: Tom Cruise’s “you complete me” dovetailing neatly into Renee Zellweger’s “you had me at hello”.

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10. Eternal Sunshine Of The Spotless Mind (2004)

Eternal Sunshine

With a Charlie Kaufman script and Michel Gondry behind the camera, Eternal Sunshine dispenses with romantic conventions for ponderous ruminations on love, memory, and painful emotion. The non-linear narrative front-loads the break-up scenes, later offering a warmer look at the happy days of the relationship between Joel (Jim Carrey) and Clementine (Kate Winslet), who make the drastic decision to forget each other entirely through a memory-erasing procedure.

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Source: RottenTomatoes

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