The 60 Best Romantic Comedies of All Time
Remember when all your angsty, lovelorn woes could be solved by a delightful (and Julia Roberts-infused) rom-com? Well, thanks to a slew of whip-smart, laugh-out-loud flicks hitting the big screen as of late, this genre is making a bit of a comeback. That’s why we’re recapping the timeless O.G.s of the rom-com era—From When Harry Met Sally to Notting Hill (and a few modern faves from Netflix, Hulu and more of our go-to streaming services). Here, 60 of the funniest, sweetest and most romantic comedies of all time.
1. While You Were Sleeping (1995)
Sandra Bullock is delightful as the token-taking "L" train employee who comes to the rescue of her crush (Peter Gallagher) after he falls on the tracks.
2. No Strings Attached (2011)
Two friends (played by Natalie Portman and Ashton Kutcher) decide to make a pact and have a no-strings attached relationship, but can they do it long enough to not break the no. 1 rule (aka falling hard for each other)?
3. Jerry Maguire (1996)
Before Tom Cruise jumped on a couch, he stole the heart of Renée Zellweger—and all of us—in this film about a sports agent in search of authenticity at work.
4. Crazy, Stupid, Love (2011)
The all-star cast (featuring Steve Carell, Julianne Moore, Ryan Gosling and Emma Stone, to name a few) is enough to press play on this rom-com that’s all about jumping back into the world of dating in your 40s.
5. My Best Friend’s Wedding (1997)
From the Dionne Warwick family sing-along to the oversize flip phones, this Julia Roberts classic had us replaying the movie soundtrack for weeks.
6. Forgetting Sarah Marshall (2008)
A trip to Hawaii is a great way to get over a breakup, but when your ex (and her new boyfriend) happens to be staying in the same hotel...well things just got a little more complicated.
7. Sleepless in Seattle (1993)
This Meg Ryan movie makes us miss the days of dialing into radio shows—and witty Nora Ephron dialogue.
8. The Half Of It (2020)
Ellie Chu agrees to write love letters for the popular jock Paul, but the catch? She’s also in love with the crush in question. The modern take of Cyrano de Bergerac, watch to the end to figure out if Ellie or Paul gets the girl.
9. When Harry Met Sally (1989)
This rom-com, about a pair of quirky New Yorkers (Meg Ryan and Billy Crystal) who believe to their core that men and women can’t be friends, changed the way we think about relationships. (Oh, and orgasms.)
10. Palm Springs (2020)
Who wouldn’t want to live the same day over and over again when Andy Samberg is involved?
11. Notting Hill (1999)
More Julia. This time with Hugh Grant—the best Horse and Hound reporter there ever was—by her side.
12. He’s Just Not That Into You (2009)
If multiple storylines about love is your thing, follow nine people (played by an incredible ensemble cast) and see how they deal with their romance woes. From misreading the signs to rediscovering your love for a significant other, everyone can connect to one couple in the flick.
13. How Stella Got Her Groove Back (1998)
Angela Bassett escapes reality for a vacation in Jamaica and meets the one, the only, Taye Diggs. Paradise found.
14. 50 First Dates (2004)
Drew Barrymore and Adam Sandler is a match made in movie gold, so it’s no surprise this rom-com will have you laughing and rooting for the couple (especially with Barrymore’s character’s short-term memory loss).
15. Four Weddings and a Funeral (1994)
A bumbling (and completely adorbs) Hugh Grant encounters the same woman (Andie MacDowell) on five separate social occasions. Romance—the British kind—ensues.
16. Coming to America (1998)
Any flick with Eddie Murphy is going to have you crying from laughter. Murphy plays Prince Akeem as he flees from an arranged marriage to find his own love in America. This ‘90s film strikes comedy gold with Arsenio Hall, James Earl Jones and Shari Headley making appearances, too.
17. My Big Fat Greek Wedding (2002)
Fotoula finally falls in love but is she prepared to have her non-Greek beau meet her traditional big Greek family?
18. Pretty Woman (1990)
Like we could omit this flick about a prostitute and a businessman (Richard Gere) who fall in love. Most importantly, we’d like to thank it for this line we reference on the regular: “Big mistake. Huge.”
19. 10 Things I Hate About You (1999)
Teenage love stories will always have a place in our hearts. The best ones brings the smart girl (Julia Stiles) and the bad boy (Heath Ledger) together for witty banter and the classic will they-won't-they debacle.
20. 13 Going on 30 (2004)
You’ve got Jennifer Garner, all the '80s tunes and a possible love for Razzles. Yes please.
21. Hitch (2005)
A dating coach (Will Smith) has no problem helping his recent client (Kevin James) win over his crush, but when it comes to his own love life, his tips and tricks simply won't do.
22. Love Actually (2003)
Eight different couples deal with their very different love lives during the month before Christmas in London. This one has it all—laughter, tears, adorable kids and Hugh Grant's killer dance moves.
23. Never Been Kissed (1999)
Josie (Drew Barrymore) didn't have the best high school experience, so when she has to go undercover as a junior for a story, she's ready for her do-over. (And she might be falling hard for her English teacher in the process.)
24. Deliver Us From Eva (2003)
Eva (Gabrielle Union) is the mother hen of her sisters and oversees the trust fund. The sisters’ significant others aren't too keen with that control and vow to distract her by setting her up with the no. 1 womanizer. The question is: Is their plan going to work or is going to completely backfire in the end?
25. Parent Trap (1998)
A rom-com you can watch with the kiddos. They'll love all the meddlesome high jinks, and you'll love reminiscing about a simpler time because if the film were set today, these two long-lost twins (played only by Lindsay Lohan) would obviously just have found each other on Facebook.
26. To All The Boys I've Loved Before (2018)
We would freak out too if letters written to every crush we ever had (oh, including our sister's boyfriend) was magically sent to them years later. But a pretend relationship might solve these problems (or make things way more complicated).
27. Moonstruck (1987)
Loretta Castorini (Cher) and Ronny Cammareri (Nicolas Cage) fall in love with each other under the moon. The only problem? She's engaged to his brother.
28. Two Weeks Notice (2002)
Lucy (Sandra Bullock) is ready to say goodbye to being more like an assistant than a lawyer to George (Hugh Grant). But when she's ready for her replacement to take the reigns, she realizes she might’ve made a huge mistake.
30. Just Wright (2010)
Leslie Wright (Queen Latifah) scores her dream job and possibly a new love (Common). The issue is, the basketball star might be the most oblivious man in the planet. (Of course).
31. Valentine’s Day (2010)
Nothing screams rom-com quite like a movie dedicated to the most romantic holiday. From first crushes to mending a broken heart, see different stories unfold on Valentine’s Day. There are so many notable celebs in this flick, we can't keep count.
32. The Wedding Planner(2001)
Mary Fiore (Jennifer Lopez) is San Francisco's best wedding planner, but she spends so much time planning other people's love stories that she doesn't have one of her own. Until fate steps in, that is, and she falls for the groom (Matthew McConaughey).
33. Think Like A Man (2012)
Four friends discover their partners have been getting love advice from Steve Harvey’s latest book and they strive to put a stop to it by turning the playbook against them.
34. You’ve Got Mail (1998)
Classic Nora Ephron with adorable characters, sizzling chemistry, punchy dialogue and a gorgeous New York backdrop.
35. Something’s Gotta Give (2003)
What happens when you have a beach house, a womanizer (Jack Nicholson) and a playwright (Diana Keaton) in one movie? A recipe for a good early 2000s love story. (Oh, and did we mention Keanu Reeves is in it?)
36. The Big Sick (2017)
This award-winning flick (based on a true story) turns the usual romantic-comedy formula on its head and tackles cross-cultural themes in a totally fresh (and funny) way.
37. Knocked Up (2007)
A one night stand turn two strangers (played by Seth Rogan and Katherine Heigl) into parents-to-be. It’s not the traditional rom-com, but you’ll be laughing from start to finish.
38. How to Lose a Guy in 10 Days (2003)
Advertising man Ben (Matthew McConaughey) has ten days to make a woman fall in love with him in order to land a prestige diamond account at his firm. Meanwhile, journalist Andie (Kate Hudson) has ten days to win and then drive away a man for the story she's writing. What happens when these two meet? We think you can guess (love, of course).
39. The Lovebirds (2020)
One couple on the verge of breaking up has to deal with clearing their name from murder. Watch Issa Rae and Kumali Nanjiani try to solve the case and mend their relationship.
40. Alex Strangelove (2018)
Alex is ready for the next step with his girlfriend and long-time best friend. But when he meets Elliot, he starts on a journey of self-acceptance and understand his sexuality.
41. Princess Bride (1987)
The perfect fairy-tale rom-com to watch when you're sick in bed. (Or any time, really.)
42. Crazy Rich Asians (2018)
Based on the bestselling book of the same title, the 2018 flick follows the journey of Rachel (Constance Wu) finding out her boyfriend (Henry Golding) is actually part of the richest family in Singapore. While processing that new info, she must also deal with his overprotective mother, conniving ex-girlfriend and this brand-new world.
43. The Proposal (2009)
We will never get over the scene of Sandra Bullock dancing and singing "Get Low" with Betty White. The 2009 flick brings Bullock and Ryan Reynolds together to fake an engagement that garners plenty of laughs.
44. Bridget Jones’s Diary (2001)
Our fave love triangle of all time. How can you choose between Colin Firth and Hugh Grant? And let’s be honest, Bridget Jones (aka Renée Zellweger) made journaling cool since 2001.
45. Set It Up (2018)
Two assistants (Zoey Deutch and Glen Powell) try desperately to get their bosses (Taye Diggs and Lucy Liu) together, while attempting to make work a little bit more bearable.
46. There’s Something About Mary (1998)
What would you do to find your high school crush? For Ted (Ben Stiller), he’ll go through great lengths to finally tell Mary (Cameron Diaz) how he feels—even if means going against the Matt Dillon.
47. Always Be My Maybe (2019)
When childhood best friends/sweethearts (played by Ali Wong and Randall Park) reconnect after 15 years, can they really continue where they left off or is it a recipe for disaster...especially when your current beau is Keanu Reeves?
48. The Holiday (2006)
You don’t need to be celebrating the holidays to watch this gem. When two women (Kate Winslet and Cameron Diaz) switch locations (ya know, before Airbnb was a thing), they discover a little more about themselves and might've found love along the way.
49. Love, Simon (2018)
Simon is dealing with typical teen woes but one thing that's been on his mind: when's the right time to come out. When he starts falling in love with anonymous person online, he wonders if this is the perfect time to finally be 100 percent himself to the people he cares about.
50. The Incredible Jessica James (2017)
FYI, breakups are the worst. Though Jessica (played by comedian Jessica Williams) and Boone (Chris O’Dowd) are game to figure it out—even if it leaves the rest of us on an emotional rollercoaster.
51. The Philadelphia Story (1940)
This '40s classic is the OG of love triangles. After Tracy Lord (Katharine Hepburn) splits with her husband (Cary Grant), she prepares to wed another. Of course, her ex-husband comes back into her life along with another reporter that steals her heart. It’s the eternal rom-com question we love to ask: Who will she end up with?
52. Clueless (1995)
This '90s flick gave us iconic one-liners (like "as if!"), impeccable fashion inspo and heartthrobs like Paul Rudd. We follow Cher (Alicia Silverstone) who gives us a glimpse into her unpredictable high school life.
53. Shakespeare in Love (1998)
Imagine a Shakespearean love story and no, we’re not talking about A MidSummer Night’s Dream or Romeo and Juliet. This ‘90s rom-com makes William Shakespeare the main character as he's involved in a forbidden relationship with an aristocrat (Gwyneth Paltrow). In order to be with him, she disguises herself as a male in one of his plays. Talk about a drama flick worth checking out.
54. 27 Dresses (2008)
Let’s be honest, we’ve all love seeing Katherine Heigl try all 27 dresses. This rom-com took being a bridesmaid to the next level and falling for James Marsden’s character is a nice touch.
55. Home Again (2017)
Reese Witherspoon is the Queen of rom-coms, so it's no surprise that she continues to make our heart melt and our eyes tear up with laughter. In Home Again she plays a mom letting three young filmmakers stay in her home; along the way she finds happiness in more ways than one.
56. Sweet Home Alabama (2002)
Speaking of Reese Witherspoon, if you have any rom-com on your list, make it this one. Melanie has it all: her dream job, her fiancé (Patrick Dempsey) and true happiness. The thing is, she's kind of still married to her high school sweetheart (Josh Lucas) back at home.
57. Roman Holiday (1953)
Princess Ann (Audrey Hepburn) decides to take a break from royal life for one night and in the process meets an American reporter Joe Bradley (Gregory Peck). While Bradley has an agenda, he soon realizes his love for the princess outweighs a hit story.
58. Mamma Mia! (2008)
Put on your dancing shoes and get ready to sing. Donna (Meryl Streep) is preparing for her daughter's wedding and her daughter (Amanda Seyfried) is trying to get to the bottom of finding out who her father is. The soundtrack includes every ABBA song you know and an all-star cast that succeeds at bringing the classic musical to the silver screen.
59. Definitely, Maybe (2008)
Ryan Reynolds should always be a narrator and this 2008 movies proves that point. Will Hayes (Reynolds) is getting a divorce and is asked by his young daughter (Abigail Breslin) about his love life before he got married. Follow along as we learn about three different women (including her mother) and figure out who he deserves to be with in the end.
60. The Best Man (1999)
Writer Harper (Taye Diggs) just penned his latest novel that may or may not have been about his friends. An advance copy just came out and he's the best man at his friend's wedding (where everyone in said book will be in attendance).