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20 Best Romantic Comedies for Anyone Who Thinks They Hate Rom Coms
Romantic comedies are not your enemy. When most people think of rom-coms—often disparagingly dubbed “chick flicks,” a term that needs to die a quick death—they probably think of bubbly, 90-minute movies featuring a Katherine Heigl or a Jennifer Aniston looking for love in all the wrong places and ultimately falling for a guy who was right there in front of her the whole damn time (but she was blinded by the fact that he was a pompous prick).
We get it. You’re probably also the kind of person who hates the sight of strangers holding hands in public or full-on making out next to the bar by the end of happy hour.
But writing off an entire genre just because a handful of its most popular examples are bad would be like refusing to listen to rock because you don’t like Nickelback. The fact is that cinema history is chock-full of great romantic comedies—maybe even a few you didn’t realize were romantic comedies. So whether you want to impress the rom-com fan in your life by happily watching one by choice or you’d just like to see a good movie on your own, check out this list of some of the best options, from the ’30s up to the present day.
New Line Cinema
20. The Wedding Singer
Adam Sandler and Drew Barrymore are really the Tom Hanks and Meg Ryan of the gross-out comedy, having appeared opposite each other in four mindless rom-coms. Their first pairing, of course, is their best. Sandler plays the titular character, the beaten-down wedding singer who falls for Barrymore’s Julia, a similarly down-on-her-luck waitress who’s engaged to a womanizing meathead. All of that’s set amid the wild and wacky 1980s, a silly premise that serves plenty of sight gags and pop-culture references. As far as dumb Adam Sandler movies go, this one is one of the sharpest.
19. Forgetting Sarah Marshall
Jason Segel bares his heart and soul (and also his junk) in this raunchy comedy about a down-on-his-luck composer named Peter whose actress girlfriend (Kristen Bell) breaks up with him after five years together. When Peter attempts to put it all behind him with a getaway to Hawaii, his plans are ruined when he winds up at the same resort as his ex and her new rock-star boyfriend. Mila Kunis, Russell Brand, Bill Hader, Jonah Hill, Jack McBrayer, and Paul Rudd round out the comic cast in his Judd Apatow-produced film.
18. Obvious Child
Girl meets boy; boy gets girl pregnant. That’s not really the typical set-up for a rom-com, which is precisely why Obvious Child is so brilliant. Jenny Slate plays a standup comedian whose lost her sense of direction, a problem only acerbated when a one-night stand with a handsome guy (Jake Lacy) leaves her pregnant. Can a romance blossom out of an awkward turn of events that lead to an abortion? You’ll end this one feeling pretty hopeful for these two kids.
17. Four Weddings and a Funeral
This Best Picture-nominated film is almost the platonic ideal of a British comedy. It does, after all, begin with a string of comic expletives as a frazzled Charles (Hugh Grant) rushes to make it to a wedding on time. It’s at that first of many social occasions that he meets Carrie, a flirty American woman played by Andie MacDowell, who quickly becomes the object of his romantic pursuit over the course of a few other weddings (and, yes, a funeral). It’s a sharp, biting comedy about romance, heartbreak, and other societal woes.
16. The Big Sick
Husband-and-wife team Kumail Nanjiani and Emily V. Gordon earned Oscar nominations for the crazy-but-true story of their courtship, starring Nanjiani as himself and Zoe Kazan as Gordon’s on-screen counterpart. When the couple break up because of their cultural differences (Kumail’s parents are pushing for an arranged marriage, per Pakistani tradition), the pair assume their shot at love is lost. But when Emily goes into a medically induced coma, Kumail is left to deal with her parents (played by a perfect Holly Hunter and Ray Romano). The trio form a bond as they watch over Emily during her illness, and it forces Kumail to come clean to his parents about his own romantic ideals and dreams.
15. Libeled Lady
William Powell and Myrna Loy shared one of the most beloved onscreen romances in Hollywood history, and in Libeled Lady it’s easy to see why. Powell plays Bill Chandler, a debonair reporter hired by the New York Evening Star to seduce a wealthy high-society woman (played by Loy) after she sues the paper for libel. Naturally, Powell soon falls for his mark in earnest, and he must decide how best to tell the love of his life that he’s been assigned to all but ruin her. It’s classic screwball romance at its most hilarious, emphasizing biting wit over sentimentality.
14. My Best Friend’s Wedding
Look, we know what you’re thinking: “Julia Roberts? Weddings? That is not a romantic comedy for people who hate romantic comedies.” And all we can say is: trust us on this one. P. J. Hogan’s 1997 comedy seems sweet and innocent on the surface, but its brilliance relies upon the fact that Roberts—still at the time America’s Sweetheart—turned the typical rom-com protagonist on her head by becoming the villain. Yes, you end up rooting for the bad guy (or girl) here as her Julianne schemes to break up the relationship between her best friend Michael (Dermot Mulroney) and his pretty, if dim, fiancée Kimmy (Cameron Diaz). Roberts smokes, swears, and sneakily manipulates everyone around her, making her character one of the greatest movie villains ever.
13. Modern Romance
Albert Brooks may not be as widely recognized as Woody Allen, to whom he’s always been compared, but Modern Romance makes a compelling case that he is in fact the greater talent. Like Allen, Brooks plays the rom-com lead as chiefly neurotic, but his genius lay in transforming anxiety and doubt into outright agony. Modern Romance isn’t as quotable as Annie Hall, but something about it will stick with you all the same. If you’ve ever suffered a bad breakup, you’ll find it almost painfully familiar.
12. Intolerable Cruelty
Only the Coen brothers could make a traditional romantic comedy co-starring two of the biggest leads in Hollywood in which an asthmatic hitman accidentally shoots himself in the head. With them, you learn to expect the unexpected. George Clooney and Catherine Zeta-Jones play a pair of evenly matched hucksters—Clooney a divorce lawyer, Jones a professional divorcee—out to fleece one another of their respective fortunes. The Coens deliver a legal comedy made in the spirit of a 1930s screwball, but with a dark touch that’s distinctly their own. More Fargo than Bridget Jones, it’s somehow both romantic and bleak.
In the 1990s Whit Stillman made a trio of literate romantic comedies that are the closest we have to modern-day versions of the classic screwballs. The best of them may be the least well-known: Barcelona, his love letter to Spanish charm about two American idiots abroad. A salesman and a naval officer on leave bumble around the streets of Barcelona trying in vain to charm the local women. The result should be relatable to any guy who’s ever spent time in a bar outside this country.
10. They Came Together
It should come as no surprise to fans of director David Wain’s spot-on teen film parody Wet Hot American Summer that his latest spoof, They Came Together, with Paul Rudd and Amy Poehler, gets everything about the romantic comedy exactly right. Wain understands that parody only works if the jokes ring true, and to that end he’s clearly done his homework: Every trope, no matter how small, comes under scrutiny, from the contrivances of backstory to the precise degree of Jewishness required of the lead. They Came Together is made for anybody who has ever had to suffer through a romantic comedy they hated, which is probably a lot of people reading this right now. It manages to vindicate your time lost to the genre.
9. The Miracle of Morgan’s Creek
Screwball comedies were always known for rapid-fire dialogue and outrageous situations, but Preston Sturges took those qualities and dialed them up to eleven. The Miracle of Morgan’s Creek, one of his best films, boasts maybe the highest quips-per-second ratio ever recorded, and there’s a good chance you’ll be laughing so hard you’ll miss about half of them. Skip the latest Adam Sandler movie and go to Sturges instead. It’s about 10,000 times funnier.
8. Chasing Amy
After making it big with Clerks and Mallrats, Kevin Smith went the somewhat traditional route and made himself a romantic comedy. But, of course, he maintained his ’90s counterculture edge and set his romance in the alternative comic book subculture, in which Holden McNeil (Ben Affleck) falls for fellow artist Alyssa Jones (Joey Lauren Adams). Of course, there’s the one complication: Alyssa is a lesbian. That doesn’t stop Holden from pursuing a friendship (and later relationship) with her, much to the chagrin of his best friend Banky (Jason Lee). Smith’s comedy sheds a light on the complications of romance and platonic love, and how dangerous mixing the two can be.
Wes Anderson’s sophomore effort introduced the world to Jason Schwartzman, here playing the eccentric polymath Max Fischer, and established his decades-long collaboration with Bill Murray, who plays Fischer’s mentor and rival Herman Blume. Both Max and Herman stumble through various pratfalls in their attempt to woo the same woman, Rosemary Cross (Olivia Williams), a teacher at the prestigious Rushmore Academy. Rushmore brings all of the best elements of a rom-com and tosses in a comedic edge and Anderson’s trademark flourish and style (and way before his signature tweeness got really old).
6. Pillow Talk
A breezy Technicolor star vehicle for Rock Hudson and Doris Day, Pillow Talk more or less invented the template modern romantic comedies would follow for years to come. Day plays a fiercely independent decorator forced to share a phone line with Hudson, a notorious playboy tying up the line night and day with his sweet-talking. The most conventional rom-com on this list, it’s also one of the most instantly likeable, with Hudson especially pulling off the charming rogue better than any star could today.
5. Broadcast News
James L. Brooks’s follow up to his Oscar-winning tearjerker Terms of Endearment didn’t earn the same amount of accolades, but it’s remained a cult classic of sorts (especially among anyone who has worked at a media company, whether it television, print, or digital news). On the surface, it’s a workplace comedy focused on news producer Jane (Holly Hunter), reporter Aaron (Albert Brooks), and aspiring anchor Tom (William Hurt). But what else would spice up the office drama like a love triangle? Aaron likes Jane, who likes Tom, who mostly likes himself. The result is a comic masterpiece that satirizes the unlucky fools who fall in love as often as it pokes fun at the ways in which television changed the news forever.
4. Trouble in Paradise
German-born director Ernst Lubitsch was the uncontested master of comic romance, and the fizzy, irresistibly risque charm of Trouble in Paradise proves it. Produced two years before the Hays Production Code rendered Hollywood sex-free, this urbane heist comedy pushed the limits of good taste and became something of a scandal in its day, and for good reason. It’s been more than 80 years and yet nobody has made movie romance seem sexier. And Herbert Marshall does the smooth criminal bit a half-century before George Clooney stepped foot in a casino.
3. The Philadelphia Story
George Cukor’s The Philadelphia Story takes nearly every element common to romantic comedies of the period—a fast-talking socialite, a pugnacious newspaperman, an impromptu wedding, and several pairs of star-crossed lovers (among them Cary Grant, James Stewart, and Katherine Hepburn, a dream cast in any era)—and throws them together to make a rom-com that’s widely considered to be the platonic ideal of the form.
2. Groundhog Day
Harold Ramis’s comic masterpiece is not only Bill Murray’s best movie ever. It’s also an essential romantic comedy, one that hides in its second half once the viewer is sufficiently braindead from all of the twisty alternate timelines. Murray is often at his best when he plays opposite talented women, and Andie MacDowell’s kind-hearted news producer is the perfect romantic foil for Murray’s cantankerous weatherman, Phil Connors. The chemistry is tight, the attraction is believable, and the happy ending is so extremely earned that you’re left wondering why it took Phil so long to get his mind right in the first place.
1. When Harry Met Sally…
Even the biggest rom-com defector cannot help but fall for Rob Reiner’s modern classic. With a screenplay by the great Nora Ephron—who may never be replaced as the foremost expert in the ways in which men and women clash with and compliment each other—and infectious and incredible chemistry by its leading couple, the film is arguably the greatest romantic comedy in movie history. Far from the middling and sappy copycats that followed in its path, When Harry Met Sally… offers essential truths about courtship, relationships, and, well, fake orgasms.