Adventureland (dir. Greg Mottola)
Greg Mottola’s comedy is a romance in disguise, buried under layers of nostalgia, weed, and Paul Westerberg. It even gave Kristen Stewart a chance to show off some actual acting abilities!
Amélie (dir. Jean-Pierre Jeunet)
You might say that the fiercely original and innovative French film is more “quirky” than comedic, but it’s certainly more of a comedy than a drama, and its last scene is one of the most romantic moments on film.
The American President (dir. Rob Reiner)
Even the leader of the free world has to get it sometimes (not that we hadn’t already learned that by the ’90s), and this charming film written by Aaron Sorkin depicts a romance between a Washington lobbyist played by Annette Bening and a bachelor president played by Michael Douglas.
The 40-Year-Old Virgin (dir. Judd Apatow)
Judd Apatow’s directorial debut is perhaps his best film (it’s the most succinct, at the very least), if only for the fact that it gave Steve Carrell and Catherine Keener the opportunity to play the lead romantic roles in a major studio comedy.
Four Weddings and a Funeral (dir. Mike Newell)
Forget your Notting Hills and your Love Actuallys. Mike Newell’s comedy is the perfect British import that balances acidic, absurdist humor with genuine sweetness.
High Fidelity (dir. Stephen Frears)
What happens when your couple breaks up at the start of your romantic comedy? A lot of male moping ensues, but it ends on a happy, hopeful note.
Kissing Jessica Stein (dir. Charles Herman-Wurmfeld)
Stars Jennifer Westfeldt and Heather Juergensen co-wrote this comedy about the perils of modern-day dating, in which a woman’s quest for the perfect man unexpectedly derails when she falls for another woman.
Much Ado About Nothing (dir. Kenneth Branagh)
William Shakespeare’s classic play might just be one of the most perfect romantic comedies, and Kenneth Branagh’s straightforward adaptation boasts an all-star cast (including Emma Thompson, Keanu Reeves, Denzel Washington, and Kate Beckinsale) and lush, exotic scenery that’ll warm you up on this cold Valentine’s Day weekend.
Muriel’s Wedding (dir. P.J. Hogan)
The titular character, played by Toni Collette, is an ABBA-obsessed Porpoise Spit, Australia native whose sole goal in life is to get married, until she embarks on a journey of self-discovery to reinvent herself as a big-city girl in Sydney.
My Best Friend’s Wedding (dir. P.J. Hogan)
A funny thing happens by the end of My Best Friend’s Wedding: although you start out rooting for the villain, you eventually come to support the romantic love between the actual couple getting married (and feel as bittersweetly satisfied as Julia Roberts’ character watching them stick together).
Next Stop Wonderland (dir. Brad Anderson)
An unlucky-in-love nurse and a hapless plumber repeatedly cross paths in Boston, never knowing how perfect for each other they really are, until serendipity finally intervenes.
The Parent Trap (dir. Nancy Meyers)
The Parent Trap is essentially two films in one: there’s the slapstick kids’ comedy, and then there’s a surprisingly tender romance between adult actors Dennis Quaid and Natasha Richardson, who — yeah, I’m saying it — play what’s perhaps the most endearing (and definitely the most attractive) romantic couple on film in the last 25 years.
Reality Bites (dir. Ben Stiller)
Ben Stiller’s directorial debut is a far cry from his later, wackier efforts like The Cable Guy, Zoolander, and Tropic Thunder, but it’s a charming romantic comedy as much as it is a pitch-perfect depiction of Gen-X ennui.
Rushmore (dir. Wes Anderson)
No love triangle in the last 25 years was more dramatic than that between Herman Blume, Rosemary Cross, and the revolutionary Max Fischer.
She’s the Man (dir. Andy Fickman)
Feel free to fight me on this: not only is this modern-day retelling of Twelfth Night the best of the teen-movie versions of Shakespeare’s plays (eat it, 10 Things I Hate About You), it’s a great reminder of the great comedic talent that was pre-Twitter Amanda Bynes.
Sleepwalk With Me (dir. Mike Birbiglia and Seth Barrish)
A sad-sack stand-up comedian struggles with romantic ennui, professional existentialism, and, naturally, sleepwalking in Birbiglia’s autobiographical tale.
Submarine (dir. Richard Ayoade)
Richard Ayoade’s coming-of-age film is a dark, absurd comedy about a teenage boy who must keep his parents’ marriage together while balancing his own budding romantic life.
Waitress (dir. Adrienne Shelley)
The late Adrienne Shelley’s film is a charming, if bittersweet, comedy about a young waitress (a radiant Keri Russell) who gets pregnant by her loser husband and then falls in love with her doctor. But most importantly, it’s a film about female self-discovery made by a talented writer-director whose career was cut tragically short.
Warm Bodies (dir. Jonathan Levine)
There are so many ways a post-apocalyptic zombie romantic comedy inspired by Romeo and Juliet could go wrong, but there are also so many ways Warm Bodies absolutely nails it.
You’ve Got Mail (dir. Nora Ephron)
Yeah, it’s dated and incredibly cheesy, but the modern-day update of The Shop Around the Corner is one of Nora Ephron’s finest film, boasting an all-star cast, unbelievable chemistry between its leads, and a pitch-perfect third act that demonstrates the best of Ephron’s abilities as a screenwriter.