The 50 Best Romantic Comedies of All Time, Ranked

Samantha Sutton | Jan 22, 2019 Movies
The 50 Best Romantic Comedies of All Time, Ranked

Clueless movie
Paramount Pictures

Sure, we enjoy a good murder mystery and suspenseful thriller as much as the next person, but when we're not in the mood to sit on the edge of our seats and actually want to get a good night’s rest? There's truly nothing like a rom-com. Watching two people fall for each other on screen -- sometimes unexpectedly -- is one of our guiltiest pleasures. And long after the credits start to roll, it's pretty much impossible to wipe that smile off our faces or keep us from daydreaming about big, romantic gestures. Plus, movies like these always manage to make us crack up and come with a handful of quotable lines.

All in all, they pretty much check all the boxes! 
Valentine's Day has come and gone, but we can still binge as many movies as we want about best friends finally falling for each other, long-lost lovers reuniting, and total opposites realizing they're actually meant to be. After all, every season is rom-com season! Still, as much as we don't mind over-the-top and cheesy (it's actually our preferred genre), there's nothing like viewing those critically acclaimed classics, either. We mean the films that got nominated for Oscars, feature a variety of A-listers (and a whole lot of Hugh Grant), and made Rotten Tomatoes's list of best romantic comedies of all time.

We're counting down from number 50 to the best-reviewed, mushy, gushy, but still hilarious movies of all time. These films are a mix of more modern hits -- like a bunch of stuff from Judd Apatow -- to old-school favorites that include stars like Audrey Hepburn and Marilyn Monroe.
  • 50. 'Crazy, Stupid, Love.'


    Rated: PG-13

    This bromance-meets-love-story has such a standout cast and is full of sweet, memorable moments that it still manages to be a favorite when it comes to rom-coms.

  • 49. 'Bridget Jones's Baby'


    Rated: R

    The third movie in the series may have come more than a decade after the original, but fans were into seeing Bridget Jones as a pregnant forty-something trying to figure out the identity of her baby's father.

  • 48. 'Me and You and Everyone We Know'


    Rated: R

    Often described as "quirky" and "offbeat," this film takes a look at searching for love and coming of age in the modern world.

  • 47. 'Clueless'

    Rated: PG-13

    An updated, humorous twist on the Jane Austen novel Emma, Clueless is a Beverly-Hills-based film where the main character, Cher, finds love in an unexpected place.
  • 46. 'Bridget Jones's Diary'


    Rated: R

    A woman is on a mission to improve herself and find love in this humorous classic.

  • 45. 'Notting Hill'


    Rated: R

    Between the cast, the chemistry, the one-liners, and memorable scenes, this one's worth watching over and over again.

  • 44. 'There's Something About Mary'


    Rated: R

    The humor in There's Something About Mary is a little crude and childish, but it's still an unforgettable film. It's essentially a movie about stalking, but there's still a lot of heart, which makes it a favorite on most people's lists.

  • 43. 'Your Sister's Sister'


    Rated: R

    The title alone hints at a complicated relationship, but it's done in a realistic, smart, and engaging way.

  • 42. 'Forgetting Sarah Marshall'


    Rated: R

    If this isn't the ultimate post-breakup movie, we don't know what is! It's hilarious, relatable, and shows that it's possible to be happy and find love again after a rough split.

  • 41. 'The 40-Year-Old Virgin'

    Giphy: BN7lNJbwgpRUA

    Rated: R

    The jokes may be a bit raunchy in The 40-Year-Old Virgin, but that -- along with the underdog story -- is what makes it so enjoyable to watch.

  • 40. '500 Days of Summer'


    Rated: PG-13

    Joseph Gordon-Levitt and Zooey Deschanel may look sweet, but they give us an honest look at complicated relationships when expectations don't line up with reality in this 2009 movie.

  • 39. 'Roxanne'


    Rated: PG

    Silly and sappy, Steve Martin plays a fire chief with a large nose who helps another man woo the girl of his dreams in this adaption of the play Cyrano de Bergerac.

  • 38. 'Maggie's Plan'


    Rated: R

    Maggie's plan is to start a family and raise her child on her own. But when she gets involved with a married professor, things get complicated in this twisted, witty love story.

  • 37. 'Breakfast at Tiffany's'


    Rated: Not Rated

    While some parts of Breakfast at Tiffany's have turned heads, the complex comedy -- which touches on identity, insecurity, and independence -- is Audrey Hepburn's most iconic role.

  • 36. 'Chasing Amy'


    Rated: R

    While many would expect a Kevin Smith movie to bring the laughs, this film also includes an insightful look at gender roles, sexuality, and relationships.

  • 35. 'When Harry Met Sally...'


    Rated: R

    Nearly 30 years later, and this story about a man and a woman attempting to be great friends -- and nothing more -- is still the gold standard.

    Plus, who can forget that restaurant scene?!

  • 34. 'Waitress'


    Rated: PG-13

    Focusing on a pregnant, pie-baking waitress who's unhappy with her life, this movie is both quirky and emotional at times.

  • 33. 'Belle Epoque (The Age of Beauty)'


    Rated: R

    Filed under the category of a sweet "sex farce," it won an Academy Award for Best Foreign Film.

    (Yeah, Belle Epoque has our attention.)

  • 32. 'Amélie'


    Rated: R

    Speaking of foreign films, this energetic and creative movie from France also made the list. It follows an eccentric girl who decides to help others find happiness, and finds love for herself in return.

  • 31. 'What's Up, Doc?'

    Rated: G 

    Barbara Streisand stars in this lovable, slapstick movie involving a bag mix-up.
  • 30. 'Sabrina'


    Rated: Not Rated

    Another winner from Audrey Hepburn! This one's a bit of a Cinderella story with humor and charm -- and really great fashion!

  • 29. 'Splash'


    Rated: PG

    In many ways, it's a live-action, adult version of The Little Mermaid -- and yes, Tom Hanks is in it!

  • 28. 'Trainwreck'

    Rated: R

    Sure, there are a few cheesy moments, but for the most part, Amy Schumer makes us laugh and relate to her as a messy, commitment-phobic career woman falling for a doctor.

  • 27. 'Obvious Child'


    Rated: R

    This film deals with some intense subjects, but does so in a raw, relatable, and, yes, witty way.

  • 26. 'Moonstruck'

    Moonstruck movie photo

    Rated: PG

    A young Cher! A young Nicholas Cage! A story about agreeing to marry the wrong guy -- and falling in love with his brother! It's worth a watch just for those factors alone.

  • 25. 'High Fidelity'


    Rated: R

    After his girlfriend walks out on him, Rob Gordon (John Cusack) looks back on other failed relationships to see why they didn't work. Plus, since he's a record store owner, the soundtrack is pretty great, too.

  • 24. 'Knocked Up'


    Rated: R

    A one-night stand turns into an unplanned pregnancy, which ultimately leads to two opposites trying to make it work.

  • 23. 'Appropriate Behavior'


    Rated: Not Rated

    For many, the style of this movie -- which follows a bisexual Persian woman trying to live up to her family's expectations -- is comparable to an episode on HBO's Girls.

  • 22. 'Born Yesterday'


    Rated: Not Rated

    This one is a political comedy that comes with the lesson not to judge a book by its cover -- especially a screechy, blond showgirl.

  • 21. 'Hannah and Her Sisters'


    Rated: PG-13

    Taking place between Thanksgiving celebrations, we get to see all the different sides of love and family: the dark parts, the complexity, and the tenderness, too.

  • 20. 'About a Boy'


    Rated: PG-13

    Hugh Grant again! This time around, the story is an emotional one: An immature, playboy-type man who gets to see what he's missing after meeting and becoming a much-needed role model for a little boy.

  • 19. 'Four Weddings and a Funeral'


    Rated: R

    There are both cheerful and tearful moments in this light, breezy classic about a man who's all about his bachelor life until he finds himself falling in love. Another Hugh Grant movie!

  • 18. 'Manhattan'


    Rated: R

    The plot point about an older man dating a teenage girl is cringey, for sure, but fans describe Manhattan as "bittersweet." (The cinematography is also pretty beautiful.)

    Plus, Meryl Streep is in it.

  • 17. 'Silver Linings Playbook'


    Rated: R

    Who would've thought football, mental illness, and dancing would be the ingredients needed for a heart-warming, energetic, and funny Oscar-nominated movie?

  • 16. 'Say Anything'


    Rated: PG-13

    This realistic coming-of-age story about the underdog and the popular girl basically set the tone for teen rom-coms to come. That boombox scene alone is iconic!

  • 15. 'The Apartment'


    Rated: Not Rated

    So he can get ahead at work, a man lends out his apartment to coworkers for their romantic trysts, only to find himself involved a complicated love situation. It's also one of the few comedies to win an Oscar for Best Picture!

  • 14. 'Groundhog Day'


    Rated: PG

    Despite the simple premise of having to relive a day over and over again, Bill Murray's iconic and hilarious performance is what has turned Groundhog Day into a classic.

  • 13. 'Enough Said'


    Rated: PG-13

    One of James Gandolfini's last roles had him playing the guy Julia Louis-Dreyfus is falling for -- who also happens to be the ex-husband of her new friend.

  • 12. 'Bringing Up Baby'

    Rated: Not Rated

    Baby is a pet leopard, Katherine Hepburn plays an heiress, and Cary Grant is the donation-seeking paleontologist.

  • 11. 'Some Like It Hot'


    Rated: Not Rated

    Two men disguise themselves as women so they can hide from the mob. But the real reason to see this one is the sexy, sweet, and brilliant Marilyn Monroe, who plays the leading lady.