50 Best Romantic Comedy Movies of All Time
Here are some of the best romantic comedies of all time. Get ready to laugh and cry as we stroll down memory lane!
'Breakfast at Tiffany's' (1961)
Holly Golightly is an eccentric New York City playgirl determined to marry a Brazilian millionaire. But when young writer Paul Varjak moves into her apartment building, her past threatens to get in their way.
'Annie Hall' (1977)
A Woody Allen classic. New York comedian Alvy Singer falls in love with the ditsy Annie Hall.
Manhattan explores how the life of a middle-aged television writer dating a teenage girl is further complicated when he falls in love with his best friend's mistress.
No sooner does Italian-American widow Loretta accept a marriage proposal from her doltish boyfriend, Johnny, than she finds herself falling for his younger brother, Ronny. She tries to resist, but Ronny lost his hand in an accident he blames on his brother, and has no scruples about aggressively pursuing her while Johnny is out of the country. As Loretta falls deeper in love, she comes to learn that she's not the only one in her family with a secret romance.
'Bull Durham' (1988)
Veteran catcher Crash Davis is brought to the minor league Durham Bulls to help their up and coming pitching prospect, "Nuke" Laloosh. Their relationship gets off to a rocky start and is further complicated when baseball groupie Annie Savoy sets her sights on the two men.
'Say Anything...' (1989)
A noble underachiever and a beautiful valedictorian fall in love the summer before she goes off to college.
'Four Weddings and a Funeral' (1994)
Over the course of five social occasions, a committed bachelor must consider the notion that he may have discovered love.
'10 Things I Hate About You' (1999)
Still one of the funniest, sweetest, and most quotable teen romcoms. We wish Heath Ledger were still here, singing "Can't Take My Eyes Off Of You."
'The Best Man' (1999)
Writer Harper (Taye Diggs) has to decide who he really loves: girlfriend Robin (Sanaa Lathan) or old flame Jordan (Nia Long). And survive the fallout from writing about all his friend's complicated love lives.
'Never Been Kissed' (1999)
Drew Barrymore is Josie, who was a geeky unpopular teen, and is now a reporter who's assigned to go undercover at a high school. She gets a crush on her English teacher (Michael Vartan) and, yes, by the end of the film, she does get her first kiss from him -- in full view of the cheering students.
'Notting Hill' (1999)
A chance encounter between an ordinary bloke (Hugh Grant) and a movie star (Julia Roberts) leads to an unexpected romance. The supporting cast is what really makes this film, especially Grant's gross roommate (Rhys Ifans). And the scene where Grant bluffs his way (terribly) through a press junket when he drops in to see Julia on the wrong day at her hotel is pure movie magic.
'Bring It On' (2000)
New cheer captain Torrance (Kirsten Dunst) has her hands full: Recruiting a new cheerleader, coming up with new (not stolen) routines, and making peace with a rival school. Is there time for the cute, mix-tape-making brother (Jesse Bradford) of new BFF Missy (Eliza Dushku)? Yes, yes there is.
'High Fidelity' (2000)
John Cusack is a record store owner (yeah, OK, this movie is 19 years old) who is obsessed with making the perfect music mix. And winning back his ex-girlfriend, who trots out a series of rebound boyfriends in front of him. Eventually (after lots of great tunes and voiceover), he gets over his fear of commitment. They reunite to a surprisingly great cover version of "Let's Get It On" by Jack Black.
'Meet the Parents' (2000)
It's an uphill battle when Teri Polo brings home fiancé Ben Stiller, who can't go 60 seconds without embarrassing himself in front of her parents. And her perfect ex, Owen Wilson. This is still silly, sublime perfection.
'Miss Congeniality' (2000)
"You think I'm sexy. You want to kiss me." Another magical Hollywood makeover turns uncouth FBI agent Gracie Hart (Sandra Bullock) into a total hottie so she can go undercover at a pageant. Fellow agent Eric (Benjamin Bratt) can't resist and we can't blame him.
'Return to Me' (2000)
In this vastly underrated romcom, grieving widower Bob (David Duchovny) meets Grace (Minnie Driver) and romance ensues. And then they both realize she, a heart transplant recipient, has his dead wife's heart. The supporting cast is terrific, including Grace's BFF, Bonnie Hunt (who also directed). The ending couldn't be more romantic. Swoon.
'Bridget Jones's Diary' (2001)
In the first Bridget Jones movie, our favorite Brit romcom heroine is torn between upper-class snob Mark Darcy (Colin Firth) and her cad of a boss (Hugh Grant). And then there's the unfortunate incident with the Playboy bunny outfit.
'Kissing Jessica Stein' (2001)
Single Jessica Stein (Jennifer Westfeldt) finds the perfect-sounding mate in the personals: Except it's a woman, not a man. She decides to roll the dice and begins a start-stop-go relationship with Helen (Heather Juergensen) in this funny, heartfelt indie.
'Legally Blonde' (2001)
Elle Woods, the most unlikely feminist icon, gets into Harvard Law to follow her douche-y ex. She ends up fighting justice on all fronts, teaching women the almighty "bend and snap," and lines up a far better bf in Luke Wilson.
'The Princess Diaries' (2001)
Mia (Anne Hathaway) finds out she's a princess and gets a fab makeover -- and ends up with the cute, guitar-playing guy (real musician Robert Schwartzman, lead singer of Rooney). Of course, by the second film there's another guy in the picture. We also love the relationship between Queen Clarisse (Julie Andrews) and her bodyguard (Hector Elizondo).
In this dreamily, gorgeous French film, imaginative Amélie (Audrey Tatou) sees the world in the most fanciful way. She finds her soulmate in Nino (Mathieu Kassovitz), who likes to collect abandoned photo booth pictures. It only gets more whimsical from there.
'About a Boy' (2002)
In this very funny film based on the Nick Hornby novel, single guy Hugh Grant pretends to be a single dad to attract single moms... all goes well until new gf Rachel Weisz learns his "son" (Nicholas Hoult) isn't his son at all. Fortunately, all is put right when he makes a complete fool of himself to save Hoult from the same fate.
'Bend It Like Beckham' (2002)
Still one of our go-to romcoms. Jess (Parminder Nagra) just wants to play football like her hero David Beckham, but her traditional family disapproves. One incentive to keep playing, the handsome coach (played by Jonathan Rhys Meyers in a rare good-guy role).
'Brown Sugar' (2002)
Taye Diggs and Sanaa Lathan are childhood friends who share a love of hip-hop -- and, they eventually admit -- each other. The soundtrack (and the music cameos) are on fire.
'My Big Fat Greek Wedding' (2002)
It's the highest-grossing romantic comedy of all time for a reason. The timeless story of how once-mousy Toula (Nia Vardalos) meets and marries Ian (John Corbett) is all the funnier thanks to her hilarious family.
'Something's Gotta Give' (2003)
In one of the most complicated of romcom relationships, Diane Keaton starts dating Jack Nicholson, who was first dating her daughter! Why she ends up choosing the unfaithful old fart over hot young doctor Keanu Reeves, we'll never know. Keaton received her fourth Best Actress Oscar nomination for the film.
'Love Actually' (2003)
What's your favorite storyline in Richard Curtis's Christmas-set smorgasbord? We're fond of author Jamie (Colin Firth) proposing to housekeeper Aurélia (Lúcia Moniz) in terrible Portuguese. And, of course, Prime Minister Hugh Grant falling for the tea girl (Martine McCutcheon). Not so much into the stalking of Keira Knightley. (Sorry, Andrew Lincoln.)
'13 Going on 30' (2004)
Jennifer Garner does "Big" in this charming romcom in which she avoids becoming a Mean Girl and ends up with the right guy after all (Mark Ruffalo). Oh and nobody cuts a rug to "Thriller" quite like her.
'The 40-Year-Old Virgin' (2005)
Geeky 40-year-old virgin Andy (Steve Carell) manages to woo Trish (Catherine Keener)... until she starts thinking his oddness means he's a serial killer! Features one of the most epic grand gesture third-act scenes set to '80s rockers Asia's "Heat of the Moment." And of course, the "Kelly Clarkson!" waxing scene.
'The Holiday' (2006)
Two unlucky-in-love women, an American (Cameron Diaz) and a Brit (Kate Winslet), swap houses for the holidays and (of course) find romance. Romcom queen Nancy Meyers wrote and directed.
Amy Adams is perfection as Giselle, an animated princess who finds herself in gritty, real-life NYC. Luckily, there's a flesh-and-blood Prince Charming Patrick Dempsey), who can't help falling for her. Favorite bit: Giselle summoning the birds -- and rats and roaches -- of the city to help her clean his apartment.
'Knocked Up' (2007)
For fun loving party animal Ben Stone, the last thing he ever expected was for his one night stand to show up on his doorstep eight weeks later to tell him she's pregnant.
Faced with an unplanned pregnancy, an offbeat young woman makes an unusual decision regarding her unborn child.
'Forgetting Sarah Marshall' (2008)
Running into your ex and her new rock star boyfriend on vacation? Awkward! Conveniently for Peter (Jason Segel), hotel concierge Rachel (Mila Kunis) is into guys on the rebound.
'Miss Pettigrew Lives for a Day' (2008)
While we do care about aspiring actress Amy Adam's many loves in this period comedy, we are far more invested in down-on-her-luck governess Miss Pettigrew (Frances McDormand) finally hooking up with well-heeled Joe (Ciarán Hinds) after several missed opportunities.
'The Proposal' (2009)
It's a bumpy ride to love for obnoxious boss Margaret (Sandra Bullock) and her beleaguered assistant Andrew (Ryan Reynolds). He agrees to act as her fiancé so she won't be deported (she's Canadian). Has that not ever led to true love in the movies?
'500 Days of Summer' (2009)
Hopeless romantic Joseph Gordon-Levitt reflects on what went wrong with ex Zooey Deschanel in this wonderfully offbeat indie.
'Just Wright' (2010)
A reminder that Rebel Wilson is not the first plus-size star to do a romcom. And that in this story that has physical therapist Queen Latifah working with injured b-ball star Common, we are so rooting for him to get wise to gold-digger Paula Patton and get with the Queen instead.
'Crazy, Stupid, Love' (2011)
Emma Stone falls for Ryan Gosling and his not-Photoshopped abs in this very funny film with almost as many romantic storylines as "Love, Actually."
Annie's life is a mess. But when she finds out her lifetime best friend is engaged, she simply must serve as Lillian's maid of honor. Though lovelorn and broke, Annie bluffs her way through the expensive and bizarre rituals. With one chance to get it perfect, she’ll show Lillian and her bridesmaids just how far you’ll go for someone you love.
'Silver Linings Playbook' (2012)
After spending eight months in a mental institution, a former teacher moves back in with his parents and tries to reconcile with his ex-wife.
'Pitch Perfect' (2012)
When Beca (Anna Kendrick) sings Jesse (Skylar Astin)'s favorite song, "Don't You (Forget About Me)," that's the key to cementing their romance. And winning the singing competition, of course.
'About Time' (2013)
Richard Curtis directs this tale of time-traveling Tim (Domhnall Gleeson), who gets endless retakes to woo the girl of his dreams (Rachel McAdams). Have your tissues ready for this one: It's as heartbreaking as it is funny.
'Enough Said' (2013)
Sadly, this change-of-pace role for "Sopranos" star James Gandolfini was one of his last: He romances Julia Louis-Dreyfus, who inconveniently is good friends with his ex (Catherine Keener). Both leads and writer/director Nicole Holofcener racked up a number of awards nominations (deservedly so).
'The Spectacular Now' (2013)
Yay, a coming-of-age Shailene Woodley romance where no one dies! Reminiscent of '80s classics like “Say Anything...,” this comedy-drama feels refreshingly real. She and Miles Teller won a Special Jury Award for Acting at the Sundance Film Fest.
'Sing Street' (2016)
Before she was Freddie Mercury's muse in "Bohemian Rhapsody,” Lucy Boynton was inspiring Cosmo (Ferdia Walsh-Peelo) to form a band, just so she can be their videos. Set in '80s Dublin, this mostly feel-good comedy from the director of "Once" is gold. Unhappily, the great original songs were overlooked at Oscar time.
'The Big Sick' (2017)
Comedian Kumail Nanjiani and real-life wife Emily Gordon wrote this Oscar-nominated film about how they met, broke up (he never even told his family about her!) and ultimately reunited. Kumail plays himself and Zoe Kazan plays Emily.
'Crazy Rich Asians' (2018)
Rachel (Constance Wu) is shocked to discover that her boyfriend Nick (Henry Golding) belongs to an incredibly wealthy family. And his mother (Michelle Yeoh) is not a fan of hers. Challenge accepted!
'Juliet, Naked' (2018)
Annie (Rose Byrne) has been in a dead-end relationship with Duncan (Chris O'Dowd) for years. He's obsessed with musician Tucker Crowe (Ethan Hawke), which, in a hilarious twist, leads to Annie hooking up with Duncan's idol. Another Nick Hornby gem.