63 Most Charming Romantic Comedies of All Time

If you’ve ever promised yourself “just one rom-com” and then looked up to realize it’s 3 a.m. and you’ve somehow watched four, this list is for you. Romantic comedies are comfort food for the soul: a little bit of laughter, a little bit of longing, a lot of happy endings, and enough quotable lines to carry you through every awkward date.

To pull together the 63 most charming romantic comedies of all time, this guide leans on a mix of critic-approved rankings, fan-favorite lists, and streaming recommendations from major outlets like Rotten Tomatoes, Marie Claire, Vanity Fair, Time, and Esquire. Across decades, you’ll see everything from black-and-white banter to modern streaming hits, plus a few offbeat choices that bend the rom-com rules in delightful ways.

Use this list as a watchlist, an argument-starter, or a cozy-night-in survival guide. However you approach it, these romantic comedy movies deliver what rom-com lovers crave: genuine chemistry, sharp humor, and endings that make you grin at your TV like it texted you “I’m outside with snacks.”

What Makes a Romantic Comedy Truly Charming?

Critics tend to define a romantic comedy as a story where the romance drives the plot and the laughs keep it afloat. Take away the love story, and the movie falls apartthat’s the basic “rom-com test.” The most charming entries usually add a few extra ingredients: sparkling dialogue, believable emotional stakes, and characters you’d happily hang out with in real life.

Charming rom-coms don’t just end in a kiss; they let you watch two people genuinely recognize and accept each otherflaws, weird hobbies, emotional baggage and all. Whether it’s a time loop in the desert, a bookstore in New York, or a royal palace in some fictional European country, the setting is really just a backdrop for that transformation.

With that in mind, let’s get to the good stuff: 63 romantic comedies that keep passing the rewatch test.

Classic Rom-Coms That Wrote the Rulebook

1. It Happened One Night (1934)

Often cited as the blueprint for the modern romantic comedy, this screwball classic pairs a spoiled heiress with a wisecracking reporter on a cross-country journey. The chemistry between Clark Gable and Claudette Colbert, plus the famous “walls of Jericho” scene, still feels surprisingly fresh.

2. The Philadelphia Story (1940)

Katharine Hepburn, Cary Grant, and James Stewart create a love triangle so clever and fizzy it might as well be bottled. On the eve of her second wedding, a socialite has to decide what (and who) she really wantsand the film juggles class satire, screwball comedy, and swoon-worthy romance with ease.

3. The Shop Around the Corner (1940)

Before You’ve Got Mail, there was this Budapest-set story of feuding coworkers secretly exchanging love letters. It’s a gentle, old-fashioned charmer that proves anonymous pen pals and workplace enemies-to-lovers have been rom-com staples for generations.

4. Roman Holiday (1953)

Audrey Hepburn plays a runaway princess, Gregory Peck a journalist who finds her napping on a Roman street. What follows is part travelogue, part fairy tale, and part bittersweet reminder that sometimes the most romantic stories don’t end in a tidy happily-ever-afterthey just leave you with a perfect day.

5. Sabrina (1954)

Another Hepburn highlight, this time as a chauffeur’s daughter torn between two wealthy brothers. The makeover elements are dated, but the movie’s heart lies in its slow realization that real love doesn’t always come in the package you expect.

6. Some Like It Hot (1959)

Two musicians disguise themselves as women to hide from gangsters and join an all-female band… and then Marilyn Monroe shows up. Wildly funny, surprisingly progressive, and endlessly quotable, it still ranks near the top of many “best comedy” and “best rom-com” lists.

7. The Apartment (1960)

Billy Wilder balances cynicism and tenderness in this story of an ambitious office worker who lends his apartment to philandering bosses, only to fall for one of their mistresses. It’s darker than a typical rom-com but ultimately lands on the side of compassion and connection.

8. Breakfast at Tiffany’s (1961)

A style icon and cultural touchstone, this film pairs Audrey Hepburn’s party girl Holly Golightly with a blocked writer and lets their guarded personas slowly crumble. While some elements haven’t aged well, the core romancetwo lost people learning to be honestis still hard to resist.

9. Barefoot in the Park (1967)

Jane Fonda and Robert Redford play newlyweds trying to make it work in a tiny New York walk-up with questionable heating. It’s a delightful portrait of the “after” part of the love story: the arguments, compromises, and laughs that come once the wedding is over.

10. Annie Hall (1977)

Love it or not, this film reshaped what a romantic comedy could beless about fairy-tale endings, more about the messy postmortem of a relationship. Its non-linear structure and neurotic humor inspired generations of more realistic, introspective rom-coms.

11. Gregory’s Girl (1980)

This Scottish coming-of-age story about a lovestruck teen goalie and the girl who takes his spot on the soccer team is quiet, awkward, and deeply charming. It’s proof that small, specific stories can feel just as romantic as Hollywood spectacles.

12. Moonstruck (1987)

Cher and Nicolas Cage fall in love over bread and opera in a movie that’s basically one long, chaotic Italian family dinner. Grand romantic gestures, sharp one-liners, and unapologetic emotion make it a perennial favorite.

13. Broadcast News (1987)

Three TV journalists navigate ambition, integrity, and attraction in a film that’s as interested in workplace ethics as it is in romance. The love triangle feels painfully real: sometimes the person who understands you best isn’t the one you end up with.

14. The Princess Bride (1987)

Part fairy tale, part swashbuckling adventure, part deadpan comedy, this cult classic doubles as a deeply sincere love story between Westley and Buttercup. “As you wish” might be the simplest, purest romantic line ever written.

15. When Harry Met Sally… (1989)

Arguably the definitive modern rom-com, this New York story tracks two friends over years of car rides, late-night calls, and big questions about whether men and women can ever just be friends. The dialogue is razor sharp, the chemistry electric, and the ending pure serotonin.

’80s and ’90s Comfort-Rom-Com Royalty

16. Pretty Woman (1990)

Julia Roberts and Richard Gere transform a Cinderella-esque premise into a full-blown star-making romance. Shopping montages, hotel piano scenes, and a fire-escape rescue cemented it as a comfort classic for millions of viewers.

17. Sleepless in Seattle (1993)

A widower on the radio, a journalist across the country, and a little boy determined to play matchmakerthis film weaponizes emotional sincerity and the Empire State Building to devastatingly sweet effect.

18. Groundhog Day (1993)

A grumpy weatherman relives the same day until he figures out how to be less of a jerk and more of a human being. Under the high-concept comedy lies a genuinely touching romance about earning someone’s love by becoming your best self.

19. Four Weddings and a Funeral (1994)

Hugh Grant practically invented the modern bumbling English rom-com hero here. Between the weddings, we get unrequited love, found family, and the kind of bittersweet humor that keeps this film high on British and American lists alike.

20. While You Were Sleeping (1995)

Sandra Bullock’s lonely transit worker saves her crush’s life, is mistaken for his fiancée, and then falls for his brother. It sounds chaotic (because it is), but the movie treats its characters with such gentleness that you can’t help rooting for everyone.

21. Clueless (1995)

Jane Austen’s Emma, but make it Beverly Hills in the ’90s. Cher’s journey from well-meaning meddler to self-aware romantic lead is full of quotable lines, iconic outfits, and one of the most wholesome “wait, I like him?” epiphanies ever filmed.

22. Notting Hill (1999)

“I’m just a girl, standing in front of a boy, asking him to love her.” That one line pretty much earned its place in rom-com history. Hugh Grant’s shy bookseller and Julia Roberts’s world-famous actress create a fantasy that still feels emotionally grounded.

23. 10 Things I Hate About You (1999)

A high-school retelling of Shakespeare’s The Taming of the Shrew, this film gave us Heath Ledger serenading Julia Stiles on the bleachers and showed that teen rom-coms could have serious emotional bite.

24. Never Been Kissed (1999)

Drew Barrymore’s undercover reporter gets a second shot at high school, and the result is equal parts cringe and catharsis. That final baseball-field scene is pure wish fulfillment for anyone who ever felt invisible as a teenager.

25. Runaway Bride (1999)

Reuniting Roberts and Gere, this small-town story about a woman who keeps literally running from the altar doubles as a rom-com about figuring out who you are outside of a relationship.

26. Bridget Jones’s Diary (2001)

Bridget’s chaotic diaries, disastrous dinner parties, and spectacularly awkward speeches turned her into an everywoman icon. The love triangle with Mark Darcy and Daniel Cleaver taps into both Austen-era courtship and modern dating disasters.

27. Amélie (2001)

This French gem follows a shy waitress who secretly orchestrates happiness for strangers while struggling to reach out to the man she likes. It’s whimsical, visually inventive, and incredibly tender.

28. My Big Fat Greek Wedding (2002)

A low-budget indie that became a huge hit, this culture-clash romance between Toula and Ian proves that sometimes the biggest obstacle to love is your own loud, opinionated, deeply loving family.

29. How to Lose a Guy in 10 Days (2003)

She’s trying to drive him away for an article; he’s trying to make her fall for him for a bet. Their dual-deception premise is delightfully chaotic, and the chemistry between Kate Hudson and Matthew McConaughey does most of the heavy lifting.

30. Love Actually (2003)

A holiday anthology of interconnected love stories, this movie has inspired fierce debates but remains a seasonal staple. Grand gestures at airport gates and doorstep cue cards have permanently entered the rom-com canon.

31. 13 Going on 30 (2004)

After a birthday wish gone wrong, a middle-schooler wakes up in her 30-year-old future body. Beyond the “Thriller” dance and candy-colored fashion, it’s a story about second chances with the childhood best friend you overlooked.

32. Hitch (2005)

Will Smith plays a “date doctor” who helps men woo the women they love, only to fumble his own romance with a sharp, skeptical journalist. Its set pieces (the allergic reaction, the disastrous jet-ski scene) are textbook rom-com mayhem.

2000s & 2010s Favorites We Can’t Stop Rewatching

33. The Holiday (2006)

Two women swap homesan English cottage and a Los Angeles mansionafter rough breakups and accidentally trade problems and love interests. Cozy vibes, adorable kids, and a gleefully charming Jack Black as a rom-com lead make it winter viewing gold.

34. Enchanted (2007)

A fairy-tale princess is tossed into real-world New York City and has to navigate modern dating norms. The film cleverly spoofs Disney tropes while still delivering a sincere, sweeping love story.

35. Knocked Up (2007)

After a one-night stand leads to an unexpected pregnancy, two mismatched people try to build some kind of partnership. It leans heavily on crude humor, but beneath that is a surprisingly heartfelt look at responsibility and compatibility.

36. The Proposal (2009)

A high-powered editor forces her assistant into a fake engagement to avoid deportation, then has to pretend to be happily in love during a family visit to Alaska. Sandra Bullock and Ryan Reynolds play off each other beautifully, turning a ridiculous premise into something disarmingly warm.

37. Easy A (2010)

Loosely inspired by The Scarlet Letter, this high-school comedy follows Emma Stone’s Olive as she uses rumor and reputation to her advantageuntil it all spirals. It’s sharp, self-aware, and features a very sweet romance tucked inside all the satire.

38. Crazy, Stupid, Love (2011)

Steve Carell’s newly single dad gets a makeover from Ryan Gosling’s smooth operator, only to discover that dating at midlife is just as confusing as teenage crushes. Interlocking storylines, a killer twist, and a now-iconic Dirty Dancing lift make it a standout.

39. Friends with Benefits (2011)

Two emotionally guarded professionals decide to add casual sex to their friendship and promise not to fall in love. Of course, they immediately break that rule. The film winks hard at rom-com clichés while happily indulging in them.

40. Silver Linings Playbook (2012)

More dramatic than most rom-coms, this story of two people working through mental health struggles and grief found a huge audienceand awards attention. The dance-competition climax somehow manages to be both absurd and deeply moving.

41. About Time (2013)

A young man discovers he can time travel within his own life and uses the power, naturally, to improve his love life. What starts as a romantic wish-fulfillment fantasy turns into a surprisingly profound meditation on family and appreciating ordinary days.

42. The Big Sick (2017)

Based on the real-life romance of Kumail Nanjiani and Emily V. Gordon, this film weaves culture clash, illness, and stand-up comedy into one of the most acclaimed rom-coms of the last decade. It’s funny, raw, and genuinely touching.

43. Love, Simon (2018)

A closeted teen navigates anonymous online romance, scheming classmates, and the fear of coming out. It’s earnest in the best way and has become a foundational queer rom-com for a new generation.

44. Crazy Rich Asians (2018)

A Chinese American professor discovers her boyfriend’s family is secretly mega-rich, then flies to Singapore to meet a future mother-in-law who is… less than thrilled. Lavish production design and a classic “prove our love” arc give this film old-school glamour with modern representation.

45. To All the Boys I’ve Loved Before (2018)

When Lara Jean’s secret love letters accidentally get mailed, she enters a fake relationship to manage the fallout. The movie nails the fluttery feeling of teenage first love and helped reignite the teen-rom-com wave on streaming.

46. Always Be My Maybe (2019)

Childhood best friends reconnect as adultsshe’s a celebrity chef, he’s stayed in their hometownand have to figure out whether they’re ready for each other this time. Beyond its heartfelt core, the movie is legendary for its extremely chaotic Keanu Reeves cameo.

47. Long Shot (2019)

A speechwriter reunites with his former babysitter, who is now a globe-trotting Secretary of State running for president. The oddball pairing, political backdrop, and surprisingly emotional script make it a modern cult favorite.

48. Palm Springs (2020)

Two wedding guests get stuck in a time loop and decide to embrace the chaos together. It’s a sci-fi twist on the “stuck together” trope, using its premise to ask big questions about commitment, purpose, and what it really means to choose someone every day.

Modern & Offbeat Rom-Coms Redefining the Genre

49. The Half of It (2020)

A shy, closeted Chinese American student ghostwrites love letters for a jock trying to win over a girlwho happens to be her own crush. This is a tender spin on the Cyrano story, full of quiet longing and unexpected friendship.

50. Set It Up (2018)

Two overworked assistants decide to “Parent Trap” their nightmare bosses into falling in love so they can finally have lives again. It’s breezy, witty, and helped prove that streaming platforms could absolutely deliver classic-feeling rom-coms.

51. The Lost City (2022)

A reclusive romance novelist and her beautiful-but-goofy cover model get swept into an actual jungle adventure. Equal parts action movie and rom-com, it leans hard into physical comedy while letting the leads slowly open up to each other.

52. Red, White & Royal Blue (2023)

The son of the American president falls for a British prince in a story that combines enemies-to-lovers banter, political complications, and fairy-tale wish fulfillment. It’s unabashedly swoony and has quickly become a streaming-era favorite.

53. Bros (2022)

A big-studio queer rom-com centered on two commitment-phobic men, this film pokes fun at the genre while embracing its emotional core. It’s self-aware, raunchy at times, and still soft where it counts.

54. Anyone But You (2023)

Modernizing the “hate each other, must pretend to be in love” trope, this Australian-set romp leans into physical comedy, big misunderstandings, and a now-famous cliffside scene involving a very inconvenient panic attack.

55. The Idea of You (2024)

A 40-year-old single mom falls for a much younger boy-band star, forcing both of them to confront fame, judgment, and their own fears about deserving happiness. It’s romantic, smart about age and power, and a reminder that love stories don’t end at 30.

56. Plus One (2019)

Two longtime friends agree to be each other’s plus-one for an entire season of weddingspure rom-com bait if there ever was one. As they zigzag through open bars, bad speeches, and bouquet tosses, the line between “fake” and “real” feelings blurs.

57. Love Jones (1997)

Set in Chicago’s Black arts scene, this slow-burn romance between a photographer and a poet mixes jazzy nightlife with serious questions about career, trust, and timing. It’s one of the most beloved Black romantic dramas with a strong comedic undercurrent.

58. Jerry Maguire (1996)

Yes, it’s also a sports movie, but at its heart this is a love story about a man rebuilding his life with the help of a single mom who sees him clearly. “You had me at hello” and “You complete me” became instant rom-com catchphrases for a reason.

59. Before Sunrise (1995)

Two strangers meet on a train and spend a single night walking and talking around Vienna. It’s quiet, talky, and almost entirely built on chemistry and conversation, but for many viewers, that’s precisely what makes it unforgettable.

60. 500 Days of Summer (2009)

This non-linear story about a greeting-card writer and the woman he falls for is less “romantic fantasy” and more “emotional autopsy.” Still, its bittersweet honesty about mismatched expectations earns it a place among modern classics.

61. Nappily Ever After (2018)

After a hair disaster forces a perfectionist to literally shave her head, she begins rebuilding her sense of selfand her love lifeon her own terms. The movie blends self-discovery with romance in a way that feels both cathartic and charming.

62. Emma. (2020)

This lush adaptation of Jane Austen’s matchmaking heroine combines pastel-perfect visuals with bone-dry humor and slow-burn romance. It pairs nicely with Clueless as proof that Austen’s romantic wit is timeless.

63. The Wedding Singer (1998)

Set in the ’80s, with all the big hair and synth-pop that implies, this movie follows a heartbroken wedding singer and a sweet waitress who slowly realize they’re perfect for each other. It’s goofy, deeply sincere, and capped off by one of the cutest airplane grand gestures in rom-com history.

How to Use This List for the Perfect Rom-Com Night

Sixty-three films might sound overwhelming, but that just means you’re prepared for every mood. Want cozy nostalgia? Reach for While You Were Sleeping, The Holiday, or 13 Going on 30. In the mood for something weirder? Try Palm Springs, The Half of It, or 500 Days of Summer. Looking for broader representation? Queue up Love, Simon, Crazy Rich Asians, Red, White & Royal Blue, and Nappily Ever After.

Mix eras, tones, and settings and you’ll start to see how the genre keeps evolvingwithout ever losing its central promise: by the end, someone will look at someone else like they’re the best thing that’s ever happened to them. And honestly, that never gets old.

Real-Life Experiences: Why These Rom-Coms Stick With Us

The reason romantic comedies endure isn’t just clever plotting or attractive leads; it’s how easily we project our own experiences onto them. Most of us have had a “meet-cute,” even if it was less bumping-into-each-other-in-a-bookstore and more “we both clicked the wrong Zoom link.” Watching characters fumble through those first impressions in movies like Notting Hill or Set It Up can feel like reliving our own awkward introductionsjust with better lighting.

Rom-coms also provide a safe way to process heartbreak and second chances. If you’ve ever stayed in a relationship too long, 500 Days of Summer hits a little too close to home, but it can also help you reframe an old breakup as part of your story rather than the end of it. Movies like About Time and Before Sunrise remind us that not every love is meant to last forever; some are there to change how we see ourselves, or what we think we deserve.

For many people, the strongest connection happens with the “found family” feeling that surrounds the central couple. Think of Bridget’s chaotic dinner parties, the sprawling clans in My Big Fat Greek Wedding or Crazy Rich Asians, or the roommate friendships in To All the Boys I’ve Loved Before. These films echo real life: our love stories rarely happen in isolation. They’re shaped by sibling advice over text, roommates who debrief every date, coworkers who notice when you start smiling at your phone more than usual.

Rom-com marathons have quietly become their own social ritual. Friends schedule “breakup recovery” nights built around When Harry Met Sally… and Crazy, Stupid, Love, complete with takeout and a standing rule that no one is allowed to text their ex until the credits roll. Couples revisit the movie they saw on their first datemaybe it was The Proposal or Love Actuallyand notice how different scenes land now that they’ve weathered a few real arguments and reconciliations of their own.

There’s also a comforting predictability in the genre’s structure. In real relationships, conflict can feel terrifying; on screen, the “all is lost” moment is practically scheduled. We know the misunderstanding in How to Lose a Guy in 10 Days or Long Shot will resolve by the 90-minute mark. That reassurance can be powerful when your own life feels messy and unresolvedit’s a reminder that miscommunications don’t have to be permanent.

Finally, the newer wave of rom-coms offers viewers the chance to see their identities and desires reflected back with more nuance. Queer audiences gravitate toward titles like Love, Simon, Red, White & Royal Blue, and Bros, while others find themselves in the cultural specificities of The Big Sick, Crazy Rich Asians, or Nappily Ever After. The more the genre expands, the easier it becomes for someone to point at the screen and say, “That’s me. That’s my family. That’s my kind of happy ending.”

In the end, these 63 romantic comedies are less a definitive ranking and more a shared language. They give us movie quotes to text, scenarios to joke about, and emotional shortcuts for things that are hard to say out loud. Whether you’re single, partnered, heartbroken, or blissfully smitten, there’s a rom-com on this list that will feel like it’s looking straight at you and saying, “Don’t worrylove stories come in all shapes, sizes, and timelines.”

Final Thoughts

From monochrome classics to neon-lit streaming hits, romantic comedies have evolved without ever losing their core promise: by the time the credits roll, someone will have taken an emotional risk and been rewarded for it. These 63 charming movies capture that leap in every possible flavorfunny, messy, swoony, and sometimes bittersweet.

So pick a title, press play, and let yourself root shamelessly for fictional people to figure it out. If nothing else, you’ll walk away with a new favorite quote, a craving for popcorn, and maybe a tiny bit more hope about your own next meet-cute.