The 19 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. Here, 19 of the funniest, sweetest and most romantic comedies of all time.
1. ‘While You Were Sleeping’
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. ‘Jerry Maguire’
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.
3. ‘My Best Friend’s Wedding’
From the Dionne Warwick family sing-along to the oversize flip phones, this Julia Roberts classic had us replaying the movie soundtrack for weeks.
4. ‘Sleepless in Seattle’
This Meg Ryan movie makes us miss the days of dialing into radio shows—and witty Nora Ephron dialogue.
5. ‘When Harry Met Sally’
Speaking of Meg Ryan and Nora Ephron, this rom-com about a pair of quirky New Yorkers (Billy Crystal included) who believe to their core that men and women can’t be friends changed the way we think about relationships. (And orgasms.)
6. ‘Notting Hill’
More Julia. This time with Hugh Grant—the best Horse and Hound reporter there ever was—by her side.
7. ‘How Stella Got Her Groove Back’
Angela Bassett escapes reality for a vacation in Jamaica and meets the one, the only, Taye Diggs. Paradise found.
8. ‘Four Weddings and a Funeral’
A bumbling (and completely adorbs) Hugh Grant encounters the same woman (Andie MacDowell) on five separate social occasions. Romance—the British kind—ensues.
9. ‘Pretty Woman’
Last Julia Roberts appearance on this list. 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.”
10. ‘13 Going on 30’
You’ve got Jennifer Garner and all the '80s tunes. Yessss.
11. ‘Love Actually’
Eight different couples deal with their very different love lives in the month before Christmas in London. This one has it all—laughter, tears, adorable kids and Hugh Grant's killer dance moves.
12. ‘Parent Trap’
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 would obviously just have found each other on Facebook).
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.
15. ‘The Wedding Planner’
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).
16. ‘You've Got Mail’
Classic Nora Ephron with adorable characters, sizzling chemistry, punchy dialogue and a gorgeous New York backdrop.
17. ‘The Big Sick’
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.
18. ‘How to Lose a Guy in 10 Days’
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).
19. ‘Princess Bride’
The perfect fairy-tale rom-com to watch when you're sick in bed. (Or any time, really.)