More than 75 years later, this Katherine Hepburn-Cary Grant-James Stewart love triangle is still the masterpiece that sits atop the upper echelon of romantic comedies. And why shouldn’t it? It’s working with the perfect formula: a wedding + too many suitors = it’s complicated.
Many regard Breakfast at Tiffany’s as the cream of the Audrey Hepburn crop, but we’d rather sleep in, then have lunch in Rome. With Gregory Peck. William Wyler’s three-time-Oscar-winning rendezvous follows a princess who lets her hair down for a day, and it’s essential Hepburn viewing.
A pair of newly-coiffed musicians (Jack Lemmon and Tony Curtis) give Marilyn Monroe a run for her sex appeal in this Billy Wilder vehicle, which follows two men who disguise themselves as women and hide in an all-female roving dance troupe after witnessing a mob hit.
Rob Reiner’s ‘80s classic tackles the age-old debate: can men and women really just be friends? There’s so much to love: the witty zingers from the pen of Nora Ephron. The comedic sincerity of Billy Crystal. And especially the big O from Meg Ryan that put Katz’s Delicatessen on the cinematic map.
For Cinderella, it was her soot-covered, raggedy reality. For Madison (Daryl Hannah), it’s a giant scaly mermaid tail she doesn’t want found out. Even though mermaids are confined to the bounds of folklore, that doesn’t stop us from believing Al (Tom Hanks) and Mad are living out their happily aquatic ever after.
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To have a rom-com roundup and not mention Rob Reiner’s adventure of Buttercup (Robin Wright) and her Westley (Cary Elwes) would be inconceivable. A love story that’s endlessly hilarious and quotable, it’s also full of action—but not that kind of action. More like pirates, sword fights, and warding off rodents of an unusual size.
Eddie Murphy and Arsenio Hall get silly in this John Landis farce, which flips the fairy-tale script: rather than fall for a peasant pretending to be a prince, the beauty here falls for a prince pretending to be a peasant. More specifically, a goat herder. It’s as rich in laughs as Prince Akeem is in gold. Here’s to the sequel!
Mike Nichols’s bromantic comedy spins a hilarious yarn with a screenplay by Elaine May and screwball genius from Robin Williams and Nathan Lane. The two play a gay couple masquerading as a straight one to appease their son’s conservative, soon-to-be in-laws. Of course, everything that could go wrong does.
Julia Roberts taps into her conniving side as Jules, who tries to woo her ex-lover-slash-best friend out of his fiancée’s arms and into her own in this Chicago-set delight. Perhaps the most “typical” rom com on this list, it does manage to reinvent the happy ending: the girl doesn’t always get the guy, and that’s OK.
Though sweet, lighthearted, and heavy on the sucrose, a sappy eye-roll rom-com full of pervasive clichés this is not. Rather, Jean-Pierre Jeunet’s Oscar bait is a Parisian fairy tale about a Montmartre waitress (Audrey Tautou) who helps others and finds love for herself along the way.
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Anything screenwriter Charlie Kaufman touches is going to be challenging, but director Michel Gondry makes good use of stars Jim Carrey and Kate Winslet to tell Kaufman’s mind-bending, Best Original Screenplay-winning story. The now-classic suggests true love does exist—even if it’s doomed.
One element of a truly great rom-com is the soundtrack. Not sure it gets better—or more romantic—than Infant Sorrow’s “Inside of You” and the other brilliant singles unleashed in this island-set comedy about breaking up and making up from Nicholas Stoller and its leading-man, Jason Segel.
Writing duo Scott Neustadter and Michael H. Weber reinvent the rom-com with a maudlin boy-meets-girl story that promises not love but heartache. That’s not to say it’s all melancholy. In fact, it has one of the happiest musical montages one could ever hope for.
Dirty jokes and defecating in the street are no longer relegated to poor-taste lampoon comedies heavy on the Y chromosomes thanks to funny ladies Kristen Wiig and Annie Mumolo, who penned this raunch wedding gem so genius it was nominated for two Oscars.
Ruby Sparks, Man Up, What If, Enough Said—the rom-com’s seen a revival, no thanks to big studios with names to match. Rather, independent film is the culprit. Perhaps the best example is The Big Sick, which stars Silicon Valley‘s Kumail Nanjiani and tells the culture-clashing true story of how he met his wife.
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This article originally appeared on Harper’s BAZAAR US.