8. Monsoon Wedding (2001)
It would be a crime to leave foreign romances off this list entirely. The Indian Monsoon Wedding is a little hard to describe, but suffice to say it plays out a little bit like Father of the Bride meets My Big Fat Greek Wedding, except, you know … Indian. The film centers on a father and daughter organizing a huge arranged marriage and family reunion, which offers an interesting inversion of a few typical Hollywood romantic comedy formulas as well as a broad satire on Indian society. It’s consistently funny and was a big domestic hit in India, with a musical adaptation poised to premiere on Broadway this year.
9. The Brothers Bloom (2008)
If The Brothers Bloom came out in 2014, we’d probably be looking at Wes Anderson-like success for the film, but way back in 2008, a lot fewer people were familiar with director Rian Johnson. Sure, there were devoted fans of his neo-noir Brick, but it wasn’t until the runaway success of 2012’s Looper that he was put on the map as an ascendant Hollywood director. This earlier tale of con men brothers was a great star vehicle for Adrian Brody and Mark Ruffalo in particular, whose performance then hinted at the comic potential he would later display as Bruce Banner in The Avengers. Rachel Weisz is especially good as the bizarre love interest who gets brought along on a continent-spanning adventure. The complicated plot is a little wonky, but the romance is sweetly endearing and Johnson gives it a fun, globe-trotting panache.
10. Casablanca (1942)
Casablanca is famous as a romance, but it’s really so many things at once. You’ve got the elements of a war film, a noir and a pulpy crime film all swirling around one of screendom’s best cases of natural chemistry between Humphrey Bogart and Ingrid Bergman. If you’ve never actually watched it, you may feel you already know everything there is to know about Casablanca, but it’s so much more than its quotable dialog and “As Time Goes By.” It grabs you and pulls you in immediately—nothing short of great popular entertainment.
11. Stranger than Fiction (2006)
Like Jim Carrey in The Truman Show, Will Ferrell deserved far more popular acclaim for his dramatic turn in Stranger than Fiction. Its excellent magical realism premise would have been enough to make for a promising film, but what Ferrell does here is wondrous—he crafts a character who is uniquely humble, reserved and average. Roger Ebert described the film as being about “quiet, sweet, worthy people,” and that is quite accurate. It’s a film that has an unexpected reserve of dignity, and its central romance between Ferrell and Maggie Gyllenhaal is seemingly mismatched but all the more genuine for it. Their first kiss is one of my favorite romantic film moments—totally vulnerable and adorable.
12. Fever Pitch (2005)
Now, as he assumes the mantle of The Tonight Show, it may be a good time to finally give Jimmy Fallon his due—although his film career has more than its fair share of bad movies (Taxi, anyone?), he put together an oddly endearing performance in this underrated, underseen flick. The premise makes you think it will simply be about Fallon’s character learning that “love is more important” than his die-hard Boston Red Sox obsession, but it ends up having a slightly deeper perspective on issues of vulnerability and abandonment. Fallon is undeniably charming, both funny and sympathetic. Drew Barrymore on the other hand is rather ditzy as the female lead, but compared to some of these other films Fever Pitch is fun, popcorn entertainment. And it’s a great way to get a sports fan to watch a romantic comedy.
13. Safety Not Guaranteed (2012)
Alright, we’re definitely on the fringes of “romance” now, but there’s still a sweet love story at the center of this down-to-earth comedy with a sci-fi premise. The relationship between Aubrey Plaza and Mark Duplass builds in unconventional and unexpected ways, and the audience is held in suspense throughout because they aren’t sure if either character’s stated feelings are a ruse. The nature of their emotions is very much dependent upon the unknown mental state of Duplass—is he crazy for thinking he can travel through time or simply an eccentric dreamer? The conclusion strikes exactly the right balance between possible payoffs.
14. Singin’ in the Rain (1952)
If Singin’ in the Rain isn’t the greatest of the classic American film musicals, then it’s at least so close as to make no difference. Sweet, earnest and genial, I personally find it a lot more entertaining than the likes of other romances such as West Side Story or Camelot. The characters are fun, and the music is incredibly infectious. If you’ve never seen it, there’s no way you’ll avoid finding yourself singing “Make ’Em Laugh,” “Moses Supposes,” “Good Morning” or the title track in the days that follow. The movie is like a well-worn pair of jeans that fits perfectly.