The 10 Most Underrated Romantic Comedies

Photo Credit:

We all know how Harry met Sally, but what about Celeste and Jesse?

Valentine’s Day is upon us, which means you’re either being swept up in a whirlwind of chocolates, roses, and fancy dinners…or you’re silently crying into your Seamless order. Still, even for those whose hearts have turned cold and black, it’s hard to deny the power of a good romantic comedy. They’re few and far in between, but when they get everything just right, they’re an instant pick-me-up.

Everyone has a list of favorites that probably includes several Woody Allen titles, something by Nora Ephron, and something starring a famous Jennifer (Garner, Aniston, Lopez, Lawrence—take your pick!). This V-Day, go for something a little more off the beaten path. Without further ado, here is a list of 10 films that, while not as well known, will make you feel the warm fuzzies all the same.


Photo Credit:'s_the_man_poster.jpg10. She’s the Man

Shakespeare is, perhaps, the ultimate expert on the ups and downs of love. This modern retelling of Twelfth Night is far from sincere, but there’s still plenty to enjoy in this tale of identity-swapping and gender role reversal at a posh boarding school. You may be quick to file this under “guilty pleasures,” but I dare you not to be entertained. At the very least, it’s a chance to watch a pre-meltdown Amanda Bynes in all her comedic excellence.


Photo Credit: How Do You Know

If you swear by Rotten Tomatoes, then you’ll probably avoid this movie like the plague. But for those willing to give this story about two people (Paul Rudd and Reese Witherspoon) trying to turn some really sh*tty lemons into lemonade a chance, prepare to be pleasantly surprised. Directed by rom-com veteran James L. Brooks, How Do You Know is what happens when a film about love stops with all the grand gestures and actually lets its characters talk to each other. The results are completely endearing.


Photo Credit: What If

Can men and women really be friends? It’s a question that time—and Hollywood—seem incapable of answering (you guys, they can…let’s just drop it). What If‘s premise is nothing new, but its dialogue is sharp, and the plot often veers away from melodrama in favor of genuine pathos. Above all, the chemistry of stars Daniel Radcliffe and Zoe Kazan is so pitch perfect, it’s hard to do anything else but watch them.


Photo Credit: About Time

This film is unabashedly sentimental, and yet there’s something so authentic about it, that it’s difficult to simply call it cheesy. The story of a young man (Domhnall Gleeson) who discovers he can travel through time isn’t the giddy journey of do-overs you’d expect. What makes this film so unique, however, is that its romance, though important, often plays second fiddle to the story of a father and son. It’s this relationship that truly melts the heart, and teaches everyone some profound facts of life.


Photo Credit: Cyrus

The mumblecore movement can, in my opinion, often do a disservice to the films it inspires, but Cyrus is not one of them. The story of a man (John C. Reilly) who falls in love with a woman (Marisa Tomei) and then has to deal with her overly-attached son (Jonah Hill) is muted, sardonic and, at times, painfully awkward. Yet, the free-flowing nature of the film’s direction lends itself to charm, and the dialogue displays the perfect amount of verity so that just about everyone can find something to identify with.


Photo Credit: Enough Said

Nicole Holofcener makes movies for adults, and I don’t mean in the X-rated way. Rather, her films exhibit a level of maturity often unseen in the rom-com genre. There are no sobbing confessionals or nasty betrayals. Instead, we get real people going through heightened situations in the most natural way possible. Sure, it might sound boring, but Enough Said taps into a lot of truths and it’s appealing in its wryness. Julia Louis-Dreyfus and the late James Gandolfini give exquisitely nuanced performances in a film that’s able to make the everyday feel very important.


Photo Credit: Crazy, Stupid, Love

Ensemble films are often hard to pull off, but Crazy, Stupid, Love balances its all-star cast nicely, giving us a multifaceted look at the world of modern dating. It’s also f*cking hysterical, and one of the few rom-coms I’ve seen that’s able to pull off consistent laughs AND a cohesive story. Unexpected, engaging, and wonderfully acted, it’s a shame this story of a family falling apart and pulling themselves back together is often overlooked. It’s really an instant classic.


Photo Credit: Going the Distance

Long-distance relationships are hard work, and no one knows that better than Erin and Garrett (Drew Barrymore and Justin Long respectively), who fall in love and end up living on opposite coasts. Though Going the Distance gives in to a few rom-com clichés here and there, its overall take on love is refreshingly modern, and it tackles the characters’ separation with a keen sense of honesty. Barrymore and Long are more than believable—they used to date in real life, after all—and the jokes are raunchier, and more enjoyable, than you’d expect.


Photo Credit: Keeping the Faith

Romantic triangles are a dime a dozen in Hollywood, but it’s the rare film that’s able to successfully examine how religion can affect our relationships with others. Featuring the talented cast of Ben Stiller, Edward Norton, and Jenna Elfman, Keeping the Faith is about a priest, a rabbi and the girl that comes between them. The film is not only a love story, but a meditation on friendship and faith in an increasingly secular world. Even the most atheistic of viewers will likely be drawn in.


Photo Credit: Celeste and Jesse Forever

The best romantic comedies are often bittersweet, and so the top spot on this list goes to a film that’s as piercing as it is pleasant. Celeste (Rashida Jones) and Jesse (Andy Samberg) are even closer now that they’re divorced, but their seemingly perfect split begins to show signs of strain as they each move in different directions. Jones proves to be a powerful screen presence, and an adept storyteller, and Samberg pairs with her perfectly. Funny, thoughtful, and deeply poignant, this is a film that really gets to the heart of what it’s like to be in love.



So, what did you think of our list? Were we spot on or dead wrong? What are some of your favorite underrated rom-coms? Sound off in the comments below!


By Mike Papirmeister

Leave a Reply

Your email address will not be published. Required fields are marked *