Whatever happened to a good old-fashioned swoon vehicle? A truly great romantic comedy, with a proper balance of desperate yearning and well-timed comic relief, is a rare occurrence in an environment where we’re too used to seeing wooden embraces; rote, passionless kisses; and dialogue that, I really hate to say it, does sound AI-generated.
It’s ironic that the rom-com — rather than, say, a straightforward drama — is seen by many as a mindless, lower form of filmic art. In fact, romance and comedy are two of the most difficult genres to write believably, and it’s even harder to do both in one script. They’re also reliant on actors who can seamlessly move between tear-jerking and jokes, and on top of their own acting abilities, the romantic leads must exude charm and a natural chemistry with each other. Put together, it’s a tall order that helps explain why there are so many bad romantic comedies out there. Thankfully, we at the Cut, united in our appreciation for this vastly underappreciated genre, have shared 25 certified-Good romantic comedies for your viewing pleasure. Grab a blanket, defrost that pint of ice cream, and enjoy!
1.
Sabrina
Not the most groundbreaking recommendation, I know, but it’s stood the test of time for a reason. Billy Wilder directs Audrey Hepburn, William Holden, and Humphrey Bogart at the top of their games as they swap longing gazes and witticisms. There’s identity confusion, physical comedy, a tennis-court dance, and the perfect deployment of “La Vie en Rose.” It just makes me happy. The 1995 remake with Julia Ormond and Harrison Ford is very good too. —Rachel Bashein, managing editor
2.
My Best Friend’s Wedding
My Best Friend’s Wedding is my slightly controversial pick for the best rom-com of the past 30 years. It doesn’t really have the happy ending you think it’s going to have, Julia Roberts’s character is absolutely not a girl’s girl, and Cameron Diaz’s character is way too young to be graduating from the University of Chicago just to get her MRS degree right away. Many people have complained to me that those are all reasons to hate this film. However, how could you deny that this movie is the perfect vehicle for demonstrating how hot Dermot Mulroney is, Rupert Everett saving the day while singing “Say a Little Prayer” with Rachel Griffiths, the stunning Chicago skyline, and taking us back to a time when writers could actually make a livable wage??? And what about the deleted alternate ending with John Corbett? Somehow this is also not the only movie in which Dermot Mulroney’s engagement ring ends up stuck on the wrong girl’s finger. —Brooke Marine, deputy culture editor
3.
10 Things I Hate About You
My desert-island rom-com has to be 10 Things I Hate About You. Based loosely on The Taming of the Shrew, it sees a beautiful Heath Ledger opposite a super-grumpy Julia Stiles (the movie opens with her reading The Bell Jar). It was filmed in my hometown, which would usually be a turnoff, but other than that it’s a perfect movie: Ledger sings “Can’t Take My Eyes Off You,” Allison Janney is a principal who writes erotica, and a teenage Joseph Gordon-Levitt plays Ledger’s scrawny sidekick. There’s also a really good paintball makeout scene. —Sangeeta Singh-Kurtz, senior writer
4.
Pride and Prejudice
The 2005 Keira Knightley version is a rom-com. I had my boyfriend watch it with me for the first time, and this typically wouldn’t be his thing, but I told him this was an 1800s rom-com and to roll with it. This man giggled and chuckled throughout the entire film. It’s sweet, somehow relatable, mildly irritating at times, and beautifully, stunningly, gorgeously shot with a stacked cast to boot. The film gods smiled upon us with this one, folks! It is the only movie I can watch over and over and over again and feel delight each time. — Danya Issawi, fashion writer
5.
A Knight’s Tale
Watching Heath Ledger joust will simply never get old. A Knight’s Tale is an anachronistic, medieval romp in which Ledger’s William Thatcher, a lowly squire, poses as a knight to compete for riches and prove he’s just as skilled as any snotty nobleman. But it’s also a romance, and Ledger is at the absolute height of his charm here. It pulls at my heartstrings every time I watch William dictate a poem to his love interest, Lady Jocelyn (Shannyn Sossamon), with assists from his hilarious hypemen (including Paul Bettany and Alan Tudyk!). And oh, how badly my preteen self wanted to be Jocelyn dancing to David Bowie with William at the tournament banquet. —Catherine Thompson, features editor
6.
You’ve Got Mail
This Nora Ephron film (based on The Shop Around the Corner) is what I refer to as “movie Xanax.” Not a single minute is unpleasant or stressful to behold. Plus, with the passage of time, many elements are just quaint now. The fact that a chain bookstore (Fox Books!) is the big bad villain. The fact that we used to get so few emails that we looked forward to hearing a robot announce when one happened to arrive. (That’s what “You’ve Got Mail” refers to, if you’re too young to remember the OG sounds of AOL.) The movie stars the couple that set the standard for contemporary romantic comedies — Meg Ryan and Tom Hanks — as Kathleen Kelly (owner of the cutest children’s-book store to ever be conjured up) and Joe Fox (owner of the aforementioned Fox Books). The retail rivals unknowingly fall in love via email, and yes, it all works out in the end with Meg Ryan in a flowy dress and Tom Hanks holding his dog’s leash in one hand. Can’t write more, must go rewatch … — Julia Edelstein, features editor, New York Magazine
7.
How to Lose a Guy in 10 Days
A classic movie about a plan gone wrong that I could watch every single year. I don’t know what it is, but Matthew McConaughey and Kate Hudson are magic together. — Brooke LaMantia, editorial assistant
8.
The Best Man
It’s a classic that makes me cry, laugh, and smile in one, and I’m obsessed with the cast, from Nia Long’s effortless ’90s beauty in the film to Morris Chestnut and Taye Diggs. I watch the sequel, The Best Man Holiday, every holiday season and I cry my eyes out. It’s a tradition for me, and my friends think I’m crazy. —Asia Milia Ware, fashion & beauty writer
9.
Moonstruck
Cher, Nic Cage, New York Italians, the opera! For me, this is a perfect movie about the way love is totally random, all-consuming, and rarely convenient. Cher won an Oscar for her performance. It’s probably one of the movies most recommended by screenwriting teachers everywhere, and for very good reason. It’s pure indulgent human romance. That’s amore. —Sasha Mutchnik, senior social editor
10.
Together, Together
As a devotee of the classic romantic comedy, I’m surprising even myself with this pick, but hear me out. I am a strong believer that loving platonic relationships can be some of the most powerful and romantic that we ever experience. In Together, Together, Ed Helms is Matt, a sort of sad dude who really wants a child; Patti Harrison is Anna, a student with a job at a coffee shop who needs to pay for the degrees she’s working toward. It’s quiet and sweet and very funny, and it features Julio Torres in an absolutely excellent bit part as Anna’s co-worker. Watching it genuinely expanded my thinking about love. —Katja Vujić, writer
11.
Something’s Gotta Give
This one is classic Nancy Meyers: beautiful kitchens with gargantuan islands, Diane Keaton in fantastic knitwear, and an affair between a playwright mother and her daughter’s much older, womanizing boyfriend (Jack Nicholson). The scene during which Keaton cries for days on end is Meyers at her best, portraying complex emotions for an age group that doesn’t always get the spotlight. And in case the aging Nicholson isn’t your thing, the movie features Keanu Reeves as a steamy doctor. —Brock Colyar, features writer
12.
Under the Tuscan Sun
I’ve watched this movie every few months since age 12. Something about it spurred my initial I-need-an-old-villa dreams. — Cortne Bonilla, fashion market editor
13.
Rye Lane
This movie is what I can only describe as a grand old time. It’s silly without being cringey, it’s beautifully filmed, and it makes you feel hopeful about love after heartbreak. It follows Yas (Vivian Oparah) and Dom (David Jonsson) after they meet in the gender neutral bathroom of their mutual friend’s art exhibition. They bond over their recent breakups and traverse South London on a moped. It also features an absolutely legendary karaoke performance of the song “Shoop,” and that fact alone makes it worth watching. — Katja Vujić, writer
14.
Angus, Thongs, and Perfect Snogging
This is one of those cheeky teen rom-coms that will make you die of secondhand embarrassment but also piss your pants with laughter. It’s British, too, which means you get exposed to all sorts of wonderful slang like “slag” (slut). — Cat Zhang, culture writer
15.
Speed
She’s a mess. He’s law and order. She’s sparky. He’s stern. Of course, love triumphs in the end. This is the smash that gave us Sandra Bullock the movie star, and when it came on cable a week or two ago, I was happy to see it holds up — and is funnier, broader, and shtickier than I remembered. It’s not a classic comedy, but it has most of the elements (the mismatched pairing, the comic-relief sidekicks, a camper-than-camp Dennis Hopper), and I contend it helped launch Bullock as a rom-com queen. (Miss Congeniality is a classic, too, by the way.) Yes, there’s a bomb on the bus. But it’s mostly the setup to a classic meet-cute. And isn’t a rom-com just a movie that makes your heart skip a beat? — Matthew Schneier, features writer
16.
Why Did I Get Married?
I don’t even know if this is considered a rom-com, but it’s one of my favorite comfort-watch movies. The dinner-table scene is historic for Black culture and I will reference it forever. — Asia Milia Ware, fashion & beauty writer
17.
Sweet Home Alabama
Sweet Home Alabama, Reese Witherspoon’s most underrated movie, is a perfect fit for anyone who’s ever wanted to adopt a fake name, move to a bigger city, and hide a secret husband. The actress plays Melanie, a haughty fashion designer who’s caught in a love triangle between the New York City mayor’s son (Patrick Dempsey) and the high-school sweetheart (Josh Lucas) she’s already married to back in Alabama. —Jordan Larson, senior editor
18.
Crazy Rich Asians
Crazy Rich Asians has all the makings of a “movie that feels like a real movie” (shout-out to Harry Styles) — from lavish production and an all-star cast to couture costumes and a setting that’s truly to die for. Nick Young, the main character played by Henry Golding, is the perfect male rom-com lead: He’s hot, rich as hell, and yet somehow still a good person. Also, this movie proves that not even a deranged mother-in-law with generational trauma can stand in the way of true love, which is a very important life lesson. —Hanna Flanagan, shopping writer/editor
19.
Easy A
Easy A is an odd nut, but as far as slightly off-kilter mainstream rom-coms go, it is in my opinion a gold standard. They let Penn Badgley play a guy whose main personality trait is not loving books; Patricia Clarkson and Stanley Tucci steal scenes as chaotic bisexual parents; and Emma Stone is Emma Stone–ing. Also: The best use of a Natasha Bedingfield song onscreen. Sorry to The Hills! — Danielle Cohen, staff writer
20.
To All the Boys I’ve Loved Before
To All the Boys helped usher in a new era of rom-com, as well as a wave of popularity for the Korean yogurt drink Yakult, and for both of these reasons and many more we must thank writer Jenny Han for the most perfectly executed teen rom-com of all time. — Katja Vujić, writer
21.
It’s Complicated
Another Nancy Meyers tryst with even more kitchen porn, but this time with Steve Martin, Alec Baldwin, and Meryl Streep. Streep is a perfect portrait of a late-middle-aged woman’s complicated desires — sleeping with her ex (Baldwin) and trying to date again after her divorce. The scene during which the three get stoned together is peak comedy-in-a-romantic-comedy. —Brock Colyar, features writer
22.
Love Actually
I have horrible taste, and part of that is loving Kiera Knightley in everything, even in this film, which is so terrible but is for some reason packed with really beautiful performances from the greats, who were persuaded to put their neck and backs into this toxic Hallmark movie. Try to get through it without crying, I dare you! — Sangeeta Singh-Kurtz, senior writer
23.
Maid in Manhattan
This movie is so ridiculous, but I can’t help but love it. It’s so unrealistic and I don’t care! Go, J.LO! However, the romantic encounters always make my heart melt, as cheesy as they are. — Cortne Bonilla, fashion market editor
24.
The Ugly Truth
The Ugly Truth is incredibly problematic, but I am obsessed with it. It follows the relationship between an uptight news producer (Katherine Heigl) and the star of a misogynistic relationship-advice show (Gerard Butler). Heigl is the most heartwarming and hilarious control freak I’ve ever seen, and Butler is the toxic, scruffy man of my dreams. The enemies-to-lovers trope between their two characters is executed so perfectly that, by the end, you will scream when they finally admit their love for each other. —Alexia LaFata, SEO editor
25.
While You Were Sleeping
I’m a sucker for a Sandra Bullock vehicle, and this is one of my favorites: She plays a ticket-booth operator who has been hopelessly pining for this one hot guy who commutes through her station every day — until he gets pushed onto the tracks and falls into a coma. She saves him and accompanies him to the hospital, where his family assumes she is his fiancée and she … lets them. Hijinks and true love ensue! — Katja Vujić, writer
