1. It Happened One Night (1934) Columbia Pictures Directed by: Frank CapraWritten by: Frank Capra and Harry CohnSocialite Ellie Andrew (Claudette Colbert) runs away and ends up crossing paths with handsome reporter Peter Warne (Clark Gable). As Peter gets Ellie's story, they begin to fall for each other. Because the film predates the enforcement of the production code, it was rather racy for the time, including a scene where Ellie shows off her leg. 2. Bringing Up Baby (1938) Turner Home Entertainment Directed by: Howard HawksWritten by: Dudley Nichols and Hagar WildeThe first of three romantic comedies starring Cary Grant and Katharine Hepburn on this list, Bringing Up Baby also stars a leopard as the titular Baby. It's a wickedly funny screwball comedy that showcases the chemistry between its two stars, who stand out even with a distractingly dangerous big cat between them. 3. Holiday (1938) Columbia Pictures Directed by: George CukorWritten by: Donald Ogden Stewart and Sidney BuchmanLike Bringing Up Baby before it and The Philadelphia Story after, Holiday stars the inimitable onscreen duo of Cary Grant and Katharine Hepburn. It's also a comedy of remarriage, as are the other two, which — by featuring divorced characters — allowed for bawdier jokes in the face of contemporary censorship. 4. The Philadelphia Story (1940) MGM Directed by: George CukorWritten by: Donald Ogden StewartSocialite Tracy Lord (Katharine Hepburn) is all set to remarry, but her wedding is thrown off course by the arrival of her ex-husband C.K. Dexter Haven (Cary Grant) and tabloid journalist Mike Connor (Jimmy Stewart). An unequivocal classic, The Philadelphia Story is largely considered the greatest of all romantic comedies. 5. His Girl Friday (1940) Columbia Pictures Directed by: Howard HawksWritten by: Charles LedererYet another comedy of remarriage, His Girl Friday stars Cary Grant as newspaper editor Walter Burns and Rosalind Russell as his ex-wife Hildy Johnson. Hildy is about to marry someone new, but she ends up entangled with Walter. If you don't know how this ends, you might want to brush up on the "comedy of remarriage" genre. 6. Roman Holiday (1953) Paramount Pictures Directed by: William WylerWritten by: William WylerCrown princess Ann (Audrey Hepburn) ditches her handlers on a tour of Rome so she can experience the city herself. She ends up crossing paths with Joe Bradley (Gregory Peck), an American reporter, and the two enjoy a whirlwind romance. While the film is a comedy, it does not — spoiler alert — end well for this unlikely couple. 7. The Apartment (1960) United Artists Directed by: Billy WilderWritten by: Billy Wilder and I.A.L. DiamondLike so many Billy Wilder films, The Apartment blends comedy and drama, but that's part of its charm. Office worker Bud Baxter (Jack Lemmon) and elevator operator Fran Kubelik (Shirley MacLaine) are both troubled, often falling for the wrong people. But through mishaps and a suicide attempt — seriously — they find each other. 8. Breakfast at Tiffany's (1961) Paramount Pictures Directed by: Blake EdwardsWritten by: George AxelrodBreakfast at Tiffany's is an unconventional pick for the genre, but then, Holly Golightly (Audrey Hepburn) is an unconventional heroine. There's a lot about the film that feels dated now — the horrific Japanese stereotype alone — but Holly's style is timeless, as is her romance with Paul Varjak (George Peppard). 9. Harold and Maude (1971) Paramount Pictures Directed by: Hal AshbyWritten by: Colin HigginsBy romantic comedy standards, Harold and Maude is very dark. Harold (Bud Cort) is a troubled young man obsessed with death, and Maude (Ruth Gordon) is a much older woman. But the love they share, however unconventional, teaches both of them about life, and it's a beautiful thing to watch. 10. Annie Hall (1977) United Artists Directed by: Woody AllenWritten by: Woody Allen and Marshall BrickmanThese days it's hard to talk about Woody Allen without acknowledging his daughter Dylan's sexual abuse allegations. At the same time, a list of the greatest romantic comedies of all time would feel incomplete without the inclusion of the funny, bittersweet Annie Hall, widely regarded as Allen's finest cinematic achievement. 11. The Goodbye Girl (1977) Warner Bros. Directed by: Herbert RossWritten by: Neil SimonAdapted from the Neil Simon play, The Goodbye Girl has oddball neurotic Elliot Garfield (Richard Dreyfuss, in an Oscar-winning role) slowly winning over dancer Paula McFadden (Marsha Mason). The two butt heads as they're forced to share an apartment along with Paula's daughter, but as is often the case, hostility turns to love. 12. Sixteen Candles (1984) Universal Pictures Directed by: John HughesWritten by: John HughesSam Baker (Molly Ringwald) is having a crappy 16th birthday, which her entire family has forgotten about. She's also consumed with feelings for hunky Jake Ryan (Michael Schoeffling). It's a typical '80s teen comedy — complete with unfortunate stereotypes and rape references — but the fairy-tale ending is still sweet. 13. Better Off Dead (1985) Paramount Pictures Directed by: Savage Steve HollandWritten by: Savage Steve HollandAfter getting dumped by his girlfriend Beth (Amanda Wyss), Lane Myer (John Cusack) tries repeatedly to commit suicide, with no success. Luckily, he ends up meeting French foreign exchange student Monique (Diane Franklin), who offers him a better alternative to preemptively ending his life over a breakup. 14. Moonstruck (1987) MGM Directed by: Norman JewisonWritten by: John Patrick ShanleyCher won a Best Actress Academy Award for her role as Loretta Castorini, a woman who is tempted away from her boyfriend Johnny Cammareri (Danny Aiello) by his younger brother Ronny (Nicolas Cage). At the same time, she has to please her very opinionated, very loud Sicilian family. 15. The Princess Bride (1987) 20th Century Fox Directed by: Rob ReinerWritten by: William GoldmanYes, it's a kissing book — or movie, in this case. The Princess Bride is so much more than just a romance or a comedy, but at the center of this fantasy adventure is the undying love between Buttercup (Robin Wright) and her farm boy turned pirate, Westley (Cary Elwes). There are no more romantic words than "As you wish." 16. Roxanne (1987) Columbia Pictures Directed by: Fred SchepisiWritten by: Steve MartinRoxanne is a modern-day update of Cyrano de Bergerac, which explains Steve Martin's sizable schnoz. He plays C.D. Bales, who writes beautiful love letters to Roxanne (Daryl Hannah) on her new boyfriend's behalf. For those who have read Cyrano, this movie ends on a much more upbeat note, thankfully. 17. When Harry Met Sally... (1989) Columbia Pictures Directed by: Rob ReinerWritten by: Nora EphronThe question of whether potential romantic interests can ever just be friends has never been more contentious than in When Harry Met Sally..., in which Billy Crystal charmed as Harry, Meg Ryan faked an orgasm as Sally, and the bar for romantic comedies — thanks to Nora Ephron and Rob Reiner — was set impossibly high. 18. Say Anything... (1989) 20th Century Fox Directed by: Cameron CroweWritten by: Cameron CroweUnderachiever Lloyd Dobler (John Cusack) romances valedictorian Diane Court (Ione Skye), despite her father's objections. Blasting Peter Gabriel on a boombox outside her house is an obvious step in the right direction — one that countless lovelorn losers have attempted in an homage to Cusack's classic '80s character. 19. Pretty Woman (1990) Touchstone Pictures Directed by: Garry MarshallWritten by: J. F. LawtonEdward Lewis (Richard Gere) is a successful businessman. Vivian (Julia Roberts) is a hooker with a heart of gold. As Vivian spends the week with Edward — for a sizable $3,000 — she charms her wealthy benefactor, and the two soon realize they have a bond that surpasses the financial arrangement that got them together. 20. L.A. Story (1991) TriStar Pictures Directed by: Mick JacksonWritten by: Steve MartinTV meteorologist Harris K. Telemacher (Steve Martin) has disappointing relationships with social climber Trudy (Marilu Henner) and ditzy model Sandy (Sarah Jessica Parker). Then he meets British journalist Sara (Victoria Tennant) and — with the help of a friendly (and sentient) freeway traffic sign — he eventually wins her over. 21. Groundhog Day (1993) Columbia Pictures Directed by: Harold RamisWritten by: Danny Rubin and Harold RamisGroundhog Day is frequently on lists of the best comedies, and yes, it's truly hilarious. Bill Murray plays selfish TV meteorologist Phil Connors, forced to repeat the same day over and over again. But beyond that, it's the story of Phil softening up to producer Rita (Andie MacDowell) and learning to make the right choices. 22. Sleepless in Seattle (1993) TriStar Pictures Directed by: Nora EphronWritten by: Nora Ephron, David S. Ward, and Jeff ArchThere are few on-screen couples as overwhelmingly likable as Sam Baldwin (Tom Hanks) and Annie Reed (Meg Ryan) in Sleepless in Seattle. The warm, funny film ends with a grand homage to An Affair to Remember on the Empire State Building: The moment is so classic it may have unseated its predecessor. 23. Muriel's Wedding (1994) Miramax Films Directed by: P. J. HoganWritten by: P. J. HoganFrumpy, awkward Muriel Heslop (Toni Collette) doesn't have a lot going for her romantically, which is a pity, as she dreams of getting married. Muriel's Wedding is as much about female friendship and finding empowerment via ABBA as it is about love, but Muriel's status as a hopeless romantic earns the film a spot here. 24. Four Weddings and a Funeral (1994) Gramercy Pictures Directed by: Mike NewellWritten by: Richard CurtisThe title says it all, doesn't it? Charles (Hugh Grant) keeps running into Carrie (Andie MacDowell) at major life events, but his attempts at courting her are thwarted by his other romantic entanglements and the fact that he's awkward and hapless when it comes to love — in other words, he's a total Hugh Grant type. 25. While You Were Sleeping (1995) Buena Vista Pictures Directed by: Jon TurteltaubWritten by: Daniel G. Sullivan and Fredric LeBowIt's kind of a funny story. Lucy Moderatz (Sandra Bullock) is obsessed with a handsome stranger named Peter (Peter Gallagher). When he ends up in a coma, she pretends to be his girlfriend and inadvertently becomes part of his family, meeting and falling for Peter's younger brother Jack (Bill Pullman). It's strange but sweet. 26. Clueless (1995) Paramount Pictures Directed by: Amy HeckerlingWritten by: Amy HeckerlingClueless is easily the greatest teen movie of the '90s, but it's also a pretty wonderful romance — the film is, after all, based on Jane Austen's Emma, and no one does romance better than Jane Austen. Spoiled rich girl Cher Horowitz (Alicia Silverstone) unexpectedly finds love with her former stepbrother Josh (Paul Rudd). 27. The American President (1995) Columbia Pictures Directed by: Rob ReinerWritten by: Aaron SorkinMichael Douglas plays President Andrew Shepherd, who has a high approval rating but no love in his life since his wife died of cancer. That all changes when he meets environmental lobbyist Sydney Ellen Wade (Annette Bening). As for how the leader of the free world dates, it's predictably complicated — and a pleasure to watch. 28. My Best Friend's Wedding (1997) TriStar Pictures Directed by: P. J. HoganWritten by: Ronald BassMy Best Friend's Wedding is one of those movies where you're not sure which couple you're rooting for. Julianne (Julia Roberts) and Michael (Dermot Mulroney) have great chemistry — but Michael is poised to marry Kimmy (Cameron Diaz). While perhaps not romantic in the traditional sense, the conclusion is still lovely. 29. Chasing Amy (1997) Buena Vista Pictures Directed by: Kevin SmithWritten by: Kevin SmithChasing Amy is not a film without controversy: After all, it involves Alyssa Jones (Joey Lauren Adams), a lesbian, falling for Holden McNeil (Ben Affleck). But try not to hold that against it. As Alyssa struggles with her confusing feelings for a man, Holden tries to hold on to the complicated woman he's fallen in love with. 30. There's Something About Mary (1998) 20th Century Fox Directed by: The Farrelly brothersWritten by: The Farrelly brothers, Ed Decter, and John J. StraussSometimes love is messy, as in the gross-out comedy There's Something About Mary, which adds a twisted (and bodily fluid-laden) edge to the traditional rom-com. Cameron Diaz stars as Mary, pined after by her high school sweetheart Ted (Ben Stiller) and Pat (Matt Dillon), the private detective Ted hired to track Mary down. 31. You've Got Mail (1998) Warner Bros. Directed by: Nora EphronWritten by: Nora Ephron and Delia EphronIn this modern update of The Shop Around the Corner — itself an adaptation of the play Parfumerie — Joe Fox (Tom Hanks) and Kathleen Kelly (Meg Ryan) fall for each other as email pen pals, despite the fact that they can't stand each other in real life. With its AOL terminology, it remains a charming late-'90s time capsule. 32. The Wedding Singer (1998) New Line Cinema Directed by: Frank CoraciWritten by: Tim HerlihyWedding singer Robbie Hart (Adam Sandler) gets left at the altar by his girlfriend Linda (Angela Featherstone). He's pulled out of his depression by waitress Julia Sullivan (Drew Barrymore), who asks for Robbie's help in planning her own wedding. The two come to realize they're more compatible with each other than anyone else. 33. Notting Hill (1999) Universal Pictures Directed by: Roger MichellWritten by: Richard CurtisA-list Hollywood star Anna Scott (Julia Roberts, basically playing herself) falls for Will Thacker (Hugh Grant), the owner of an independent bookstore in Notting Hill. Watching the two connect despite their very different lives is a delight, and Anna's "I'm just a girl, standing in front of a boy, asking him to love her" line is classic. 34. Never Been Kissed (1999) 20th Century Fox Directed by: Raja GosnellWritten by: Abby Kohn and Marc SilversteinYou kind of have to ignore the fact that for much of Never Been Kissed, Josie Geller (Drew Barrymore) is falling for a man who thinks she's a teenager. But it all works out in the end! Reporter Josie is actually undercover as a high school student, and her romance with teacher Sam Coulson (Michael Vartan) ends up being her story. 35. The Best Man (1999) Universal Pictures Directed by: Malcolm D. LeeWritten by: Malcolm D. LeeOn the eve of his best friend Lance's (Morris Chestnut) wedding, author Harper Stewart (Taye Diggs) is struggling with his feelings for girlfriend Robin (Sanaa Lathan) and mixed reactions to a leaked manuscript of his autobiographical novel. The smash hit sequel, The Best Man Holiday, was released in 2013. 36. 10 Things I Hate About You (1999) Buena Vista Pictures Directed by: Gil JungerWritten by: Karen McCullah Lutz and Kirsten SmithIn this high school rom-com update of Shakespeare's Taming of the Shrew, bad boy Patrick (Heath Ledger) tries to woo Kat (Julia Stiles) so that Cameron (Joseph Gordon-Levitt) can date Kat's popular younger sister Bianca (Larisa Oleynik). 10 Things I Hate About You is smart, funny, and feminist — unlike the original play. 37. But I'm a Cheerleader (1999) Lionsgate Directed by: Jamie BabbitWritten by: Brian Wayne PetersonMegan (Natasha Lyonne) can't be a lesbian — she's a cheerleader. But as she soon learns at reparative therapy camp to "cure" homosexuality, Megan does harbor same-sex feelings. The object of her affection is Graham (Clea DuVall), another girl at camp. And yes, as Megan comes to terms with her sexuality, her parents do too. 38. High Fidelity (2000) Buena Vista Pictures Directed by: Stephen FrearsWritten by: D.V. DeVincentis, Steve Pink, John Cusack, and Scott RosenbergWhen romantically inept music nerd Rob Gordon (John Cusack) gets dumped by his girlfriend Laura (Iben Hjejle), he sets out to contact his exes to discover why he's always had trouble with women. In the process, of course, he learns how to be a better boyfriend to Laura — and a better person overall. 39. Kissing Jessica Stein (2001) Fox Searchlight Pictures Directed by: Charles Herman-WurmfeldWritten by: Heather Juergensen and Jennifer WestfeldtLike Chasing Amy, Kissing Jessica Stein isn't the most beloved rom-com among lesbians — in the end, Jessica (Jennifer Westfeldt) ends up (spoiler alert) going back to men. And yet, it's still a nice look at sexual exploration, with Jessica trying something new and dating bisexual Helen Cooper (Heather Juergensen). 40. Bridget Jones' Diary (2001) Miramax Films Directed by: Sharon MaguireWritten by: Andrew Davies and Richard CurtisClumsy, curvy Bridget Jones (Renée Zellweger) is desperate to find a man, lusting after her boss Daniel Cleaver (Hugh Grant) while also romancing good guy Mark Darcy (Colin Firth). The latter is clearly the right choice, but Bridget flits between the two, all while recording her deepest thoughts and pithy observations in her diary. 41. All Over the Guy (2001) Lionsgate Films Directed by: Julie DavisWritten by: Dan BucatinskyAll Over the Guy was one of the very first gay romantic comedies — and it's still the best. Sadly, there isn't much competition, because although the film showed how great a gay rom-com could be, few filmmakers have attempted the feat. Here, screenwriter Dan Bucatinsky stars as Eli alongside Richard Ruccolo as Tom. 42. About a Boy (2002) Universal Pictures Directed by: Chris Weitz and Paul WeitzWritten by: Peter Hedges, Chris Weitz, and Paul WeitzAbout a Boy is — well, about a boy, specifically Marcus Brewer (Nicholas Hoult), who finds an unlikely parental figure in Will Freeman (Hugh Grant). But as Will grows up and learns how to be a father of sorts to Marcus — past using him to pick up women — he sparks a connection with single mother Rachel (Rachel Weisz). 43. Brown Sugar (2002) Fox Searchlight Pictures Directed by: Rick FamuyiwaWritten by: Michael Elliot and Rick FamuyiwaBrown Sugar tells the familiar story of lifelong friends who realize they might be something more — at the most inopportune time possible. Dre Ellis (Taye Diggs) is engaged to marry Reese (Nicole Ari Parker), but then there's his best friend Sidney Shaw (Sanaa Lathan). Chances are you know how this one turns out. 44. Something's Gotta Give (2003) Columbia Pictures Directed by: Nancy MeyersWritten by: Nancy MeyersIt's rare to see a romantic comedy starring people of a certain age, which is why Something's Gotta Give was so refreshing. Music mogul Harry Sanborn (Jack Nicholson) finds himself drawn to playwright Erica Barry (Diane Keaton), despite the fact that they're total opposites — and Harry usually dates much younger women. 45. How to Lose a Guy in 10 Days (2003) Paramount Pictures Directed by: Donald PetrieWritten by: Michele Alexander, Jeannie Long, Kristen Buckley, Brian Regan, and Burr SteersOK, the two leads in How to Lose a Guy in 10 Days are obnoxious, but that's the point! Andie Anderson (Kate Hudson) is writing the titular article and purposely driving off the guy she's dating, but Benjamin Barry (Matthew McConaughey) has bet that he can get a woman to fall in love with him in 10 days. Yes, hilarity ensues. 46. Love Actually (2003) Universal Pictures Directed by: Richard CurtisWritten by: Richard CurtisThe debate over the merits of Love Actually rages on, but as those who defend it know, it's hard to beat these delightfully eclectic interconnecting love stories — from prime minister David (Hugh Grant) and member of his staff Natalie (Martine McCutcheon) to writer Jamie (Colin Firth) and his housekeeper Aurélia (Lúcia Moniz). 47. 13 Going on 30 (2004) Columbia Pictures Directed by: Gary WinickWritten by: Josh Goldsmith and Cathy YuspaIt's hard enough trying to date as an adult, but even harder when you're actually a 13-year-old girl inside. Jenna Rink (Jennifer Garner) is thrust 17 years into the future, where she finds herself drawn to her (now fully grown) childhood friend Matt Flamhaff (Mark Ruffalo). Like most fairy tales, this one comes with a happy ending. 48. Imagine Me & You (2005) Fox Searchlight Pictures Directed by: Ol ParkerWritten by: Ol ParkerEven though Rachel (Piper Perabo) is about to marry Hector (Matthew Goode), she can't deny her attraction to flower shop owner Luce (Lena Headey). Imagine Me & You focuses mostly on Rachel's attempts to make sure she's marrying the right person, and not on the fact that her new crush happens to be a woman. 49. The 40-Year-Old Virgin (2005) Universal Pictures Directed by: Judd ApatowWritten by: Judd Apatow and Steve CarellSteve Carell stars as Andy Stitzer, a man who somehow made it to 40 as a complete virgin. While the film is ostensibly about his attempts to get laid, it's also about Andy finding a real relationship with single mom Trish Piedmont (Catherine Keener), who finally — spoiler alert — rids Andy of his unintentional celibacy. 50. Music and Lyrics (2007) Warner Bros. Pictures Directed by: Marc LawrenceWritten by: Marc LawrenceWashed-up pop star Alex Fletcher (Hugh Grant) discovers songwriter Sophie Fisher (Drew Barrymore), and the two combine forces professionally — and then, of course, romantically. Music and Lyrics doesn't exactly reinvent the rom-com wheel, but Grant and Barrymore are genre stars for a reason, and they're as charming as ever. 51. Nick and Norah's Infinite Playlist (2008) Columbia Pictures Directed by: Peter SollettWritten by: Lorene ScafariaThe titular Nick and Norah, Nick O'Leary (Michael Cera) and Norah Silverberg (Kat Dennings), wander all over New York City to find a secret show by reclusive indie band Where's Fluffy? Beneath all the aggressive hipness, there's a very sweet love story, as Nick and Norah cross paths and forge a genuine bond with each other. 52. Forgetting Sarah Marshall (2008) Universal Pictures Directed by: Nicholas StollerWritten by: Jason SegelIt's not a comedy of remarriage, but Forgetting Sarah Marshall does seem to be going in that direction for a while, as Peter Bretter (Jason Segel) tries to win back his ex Sarah Marshall (Kristen Bell). What he finds is that they were never a great match to begin with, and that hotel concierge Rachel (Mila Kunis) is a better option. 53. The Proposal (2009) Walt Disney Studios Motion Pictures Directed by: Anne FletcherWritten by: Pete ChiarellMore charming than it has any right to be, The Proposal follows tough publisher Margaret Tate (Sandra Bullock), who — to prevent getting deported to Canada — arranges a sham marriage with her assistant Andrew Paxton (Ryan Reynolds). When she goes to visit his Alaskan family, they fall in love, because Ryan Reynolds. 54. Going the Distance (2010) Warner Bros. Directed by: Nanette BursteinWritten by: Geoff LaTulippeAnyone who has ever experienced the highs and lows of long-distance dating can appreciate Going the Distance, one of the most underrated romantic comedies in recent years. Erin (Drew Barrymore) and Garrett (Justin Long) struggle to make things work, while their respective jobs keep them hundreds of miles apart. 55. Easy A (2010) Screen Gems Directed by: Will GluckWritten by: Bert V. RoyalEasy A is more about female independence than it is about finding love. And yet, it is romantic. Olive Penderghast (Emma Stone) gets labeled a slut after false rumors spread, but rather than hide her head in shame, she owns her new reputation. Todd (Penn Badgley) is the good guy who accepts Olive for who she really is. 56. Safety Not Guaranteed (2012) FilmDistrict Directed by: Colin TrevorrowWritten by: Derek ConnollySafety Not Guaranteed is a little more complicated than your average romantic comedy, and not only because it may involve time travel. It's about cynical Darius Britt (Aubrey Plaza) and eccentric (possibly insane) Kenneth Calloway (Mark Duplass). The conclusion of their strange romance is genuinely breathtaking. 57. Moonrise Kingdom (2012) Focus Features Directed by: Wes AndersonWritten by: Wes Anderson and Roman CoppolaAh, young love. Moonrise Kingdom follows Sam Shakusky (Jared Gilman) and Suzy Bishop (Kara Hayward) as they go on the run in 1965. Their relationship is mostly innocent and completely inept, but that's the charm. Well, that and Wes Anderson's incomparably twee style. As always, pastel colors abound. 58. Enough Said (2013) Fox Searchlight Pictures Directed by: Nicole HolofcenerWritten by: Nicole HolofcenerThere's a bittersweet quality to Enough Said, both because it's a Nicole Holofcener film, and because star James Gandolfini died suddenly shortly before the film premiered. But it's a sweet story about finding love at a certain age, as Gandolfini's Albert tries dating masseuse Eva (Julia Louis-Dreyfus) despite their differences.