Romantic comedies have always been popular. It’s why Hallmark religiously releases a string of sappy tales of love every Christmas and New Year. Despite often being critiqued for its dependence on tropes, this genre of films has still shaped our perceptions of love since forever. After all, who doesn’t dream of meet-cutes in cozy cafes, airport chases that end in hugs and kisses and ardent declarations of adoration, and a beautiful boy holding a boombox in the rain? Not all romantic comedies do it well, though, but some are great enough to enjoy a cult following and proudly stand the test of time.
Timeless and elegant, the films are the OG classics, crème de la crème, the unbeautiful. The best of these have been listed below.
1) You’ve Got Mail
Directed by Nora Ephron, this 1998 movie features the story of Joe Fox (Tom Hanks) and Kathleen Kelly (Meg Ryan) as they slowly fall in love with each other in the virtual realm while constantly clashing in real life as business rivals. Ryan and Hanks are hands down the OG king and queen of rom-com, creating magic every time they meet on screen, and this film is no different. Ryan plays a playful, old-school romantic and the owner of an independent bookstore that once belonged to her mother. Hanks, on the other hand, is all about modernism and franchises, quickly robbing Ryan’s store of its once loyal customers. The latter, of course, hates him for it, and the two clash time and again as if they’re oil and water. Unbeknownst to them, their online personas were slowly yet surely falling head over heels for each other, one anonymous Yahoo! mail at a time.
You can stream You’ve Got Mail on Prime Video.
2) Sleepless in Seattle
Tom Hanks and Meg Ryan again star in this 1993 love story that is nearly as heartwarmingly beautiful as You’ve Got Mail. Sleepless in Seattle has a cult following of its own, and why wouldn’t it? Tom Hanks’s character — Sam — offers up a melancholy charm as the heartbroken widower who can’t think of finding love again. Fate and his son have other plans, though. His son’s pleas lead him to share his story over the radio. And a beautiful end may await him atop the Empire State building, in the form of another woman, on a cold night in the middle of February.
You can stream Sleepless in Seattle on Prime Video.
3) When Harry Met Sally
Meg Ryan plays Sally in this 1989 romantic comedy that shows two friends fall in love despite having completely opposing views on love. Through the years, Harry and Sally hang out many times, each meeting highlighting how different they are from each other. But they also have an easy camaraderie between them, the kind that lets you be truly comfortable and be who you are.
It’s easy to see why When Harry Met Sally is considered a classic. At a time when films were focusing on beautiful, perfect leads falling in love at first sight, it had the guts to show two perfectly imperfect people fall in love. The cinematography is beautiful. Meg Ryan is exquisite, as per usual. Also, the iconic scene where Ryan’s character starts loudly moaning in a diner to show Harry how women fake orgasms alone gives the film a lot of rewatch value.
You can stream When Harry Met Sally on Prime Video.
4) Notting Hill
This 1999 movie features Hugh Grant in all his boyish glory and the heartbreakingly beautiful Julia Roberts. It is no question that Julia Roberts rules the screen, what with her Mona Lisa smile and impeccable sense of fashion. But Hugh Grant’s victory lies in the cheesy, charming, adorably awkward heart of the movie. If you love stories where two different worlds collide and mingle, then Notting Hill will offer you a subtle waltz of it.
It will offer you drama, sweetness, despair, and joy. Notting Hill will tell you what happens when one movie star, an international sensation, falls in love with a small-town bookseller, a regular person in all senses of the word. It will steal your heart with one line about one girl, standing in front of a boy, asking him to love her.
You can stream Notting Hill on Prime Video.
5) Pretty Woman
Richard Gere, one of Hollywood’s classic charmers with a bad boy image, and Julia Roberts, before whom adjectives fall short, star in this movie. Pretty Woman tells the story of Edward (Richard Gere) — a wealthy entrepreneur — who slowly and irrevocably falls in love with Vivian (Julia Roberts), a sex worker as alluring as she is endearing. Two very different worlds collide and tangle as their seemingly doomed story unfolds. Will love be enough to help them unite and rise above their situations? That, gentle reader, is for you to find out.
You can stream Pretty Woman on Prime Video.
6) 10 Things I Hate About You
A 1999 film directed by Gil Junger, 10 Things I Hate About You is, as any rom-com aficionado worth their salt knows, not a movie that you can afford to miss. This is an enemies-to-lovers story where Julia Stiles’s character, Kat, slowly falls in love with charming, mysterious Patrick (Heath Ledger). Trouble ensues when Kat discovers that Patrick was hired by her brother to charm her so the latter can date his crush. But this is not a story about betrayal and heartbreak. It is about love, in its many truths and lies; in its heartaches, but mostly in its joys.
You can stream 10 Things I Hate About You on Disney+.
7) Bridget Jones’ Diary
No list of rom-coms can be considered even close to complete if they do not mention this hilariously disarming film with oodles of rewatch value. After all, Bridget Jones, in all her clumsiness, is as relatable today as she was when we first encountered her curled up on a sofa with a tub of heartbreak-flavored ice cream. Bridget is not like other female leads, thin and self-assured. She is not great at charming her crushes or flirting her way into people’s hearts. She is awkward and goofy, and she faceplants a few times in her pursuit of love. But Mr. Darcy, played by none other than the breathtakingly beautiful Colin Firth, seems to like her just as she is, even if she is a tad silly.
You can stream Bridget Jones’ Diary on Prime Video.
8) About Time
About Time is many things, forgettable is not one of them. Yet it remains criminally underrated, rarely winning a well-deserved spot among other classics. The film is about love, of course, but it is also about the importance of time, of taking each day and living it like it’s one’s last, for it very well could be. The male lead, Tim (Domhnall Gleeson), is dorky yet determined in his search for love. And when he finds it in Mary, played by the ravishing Rachel McAdams, he uses everything in his power to make her fall in love with him again and again. This film has everything — a great storyline, beautiful cinematography, time travel, and Bill Nighy as Tim’s wise, wonderful dad. It reminds us that no day is imperfect or unimportant as long as you’re alive and around the ones you love.
You can watch About Time on Prime Video and Apple TV.
9) The Holiday
Cameron Diaz, Jack Black, Kate Winslet, and Jude Law play the main leads in this 2006 film directed by Nancy Meyers. It tells the story of two women, living on opposite sides of the world, who swap their houses to escape the disaster that is their love lives. Kate’s character has been forever in love with her friend, who keeps toying with her feelings. Diaz’s character is jaded and can’t seem to make a relationship last. Faced with the choice of being stuck in their stifling situations, they decide to swap houses during Christmas, to try to escape love and its many issues. Fate seems to have other plans, though, and each woman meets a stranger who takes their breath away. The entire film is cozy, the casting is impeccable, and the writing is unique enough to turn this into a tale of love and longing that remains relevant nearly two decades after its release.
You can stream The Holiday on Netflix.
10) Breakfast at Tiffany’s
A true classic among classics, Breakfast at Tiffany’s features the incredible Audrey Hepburn at the peak of her career as the female lead. The film tells the story of a struggling author (George Leppard) who moves into a new apartment, only to be inundated with the eccentricities of his socialite neighbor, Holly. Leppard’s character is helpless before Hepburn’s quirks, falling for her slowly and irrevocably. He witnesses sides of her that she keeps from her other socialite friends, hiding heartbreak beneath easy smiles and bad decisions.
You can stream Breakfast at Tiffany’s on Prime Video.
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