Is there anything more delightful and life-affirming than a perfectly executed romantic comedy?
Every once in awhile, it’s nice to indulge our inner sap and just let our cynical expectations disappear as we sit back, grab a bucket of popcorn, pull up our Snuggie and pop in a cheesy feel-good (and completely unrealistic) rom-com. So here’s ten romantic comedies we recommend for those days when you just feel like falling in love.
1) The Princess Bride (1987)
Westley: This is true love – you think this happens every day?
The quintessentially perfect book to screen adaptation, this film teaches us that even death cannot stop true love… it can only delay it for a while.
With its dashing pirates, deadly sword fights, and large animatronic rodents, The Princess Bride isn’t the traditional “kissing-book” romantic comedy. Its ironic humor makes it about so much more than the central romance, simultaneously mocking and yet believing in the power of this ultimate true love between a former stable boy and would-be princess.
2) 10 Things I Hate About You (1999)
Patrick: Ooh, see that, there. Who needs affection when I have blind hatred?
It’s hard to really mess up material from the king of romantic comedies himself, but this modern day interpretation of Shakespeare’s 400 year-old rom-com The Taming of the Shrew, shows us that despite hundreds of years of technological advancement, human behavior and emotion hasn’t really changed all that much through the generations.
And while we do not condone the objectification of women through a misogynistic bet, it’s hard to stay mad at a guy who literally did a song and dance routine in an attempt to win a lady’s affections.
3) You’ve Got Mail (1998)
Joe Fox: Don’t you love New York in the fall? It makes me want to buy school supplies. I would send you a bouquet of newly sharpened pencils if I knew your name and address. On the other hand, this not knowing has its charms.
It’s a real Sophie’s Choice trying to pick between Nora Ephrom’s two classic rom-coms starring Meg Ryan and Tom Hanks, but in the end this sequel of sorts to Sleepless in Seattle wins out because we get to watch these two fall in love twice: first as cyber pen pals, and later as enemies turned best friends.
Meg Ryan looks absolutely adorable in all of her granny sweaters, and makes us believe in the beauty of daisies as we wish we could all look so precious with a head cold. And everyone in this film works in a bookshop, which is just cool.
4) Penelope (2006)
Penelope: Once the Queen is dead, the King is useless.
Max: What’s that about?
Penelope: I don’t know. Maybe he’s too depressed to fight. He really loved her, you know.
This romantic comedy features Peter Dinklage as a cynical detective, James McAvoy as a jaded gambler who’s lost his musical soul, and Reese Witherspoon as a sassy
biker moped chick. Most importantly, Christina Ricci is the pig-faced damsel in distress who learns to slay her own dragons.
This quirky Beauty and the Beast interpretation turns the classic story on its head as the characters inspire one another to find their own strength as individuals, and proves that the most important person we have to learn to love is our self. Also, how cute are those chess scenes?
5) Music and Lyrics (2007)
Alex: The best time I’ve had in the last fifteen years was sitting at that piano with you.
Sophie: That’s wonderfully sensitive… especially from a man who wears such tight pants.
Alex: It forces all the blood to my heart.
This vastly underappreciated romantic comedy is wonderful in its simple, yet effective execution. Hugh Grant does what he does best and exploits his rom-com leading man status as a fallen pop star of the 80’s, while Drew Barrymore is adorable as his kooky plant-lady turned songwriter.
The actors are truly delightful in their chemistry, and their line delivery is absolutely spot-on as they make corny lines seem downright funny. Also, this cheesy pop soundtrack is just super catchy.
6) Breakfast at Tiffany’s (1961)
Paul Varjak: You know what’s wrong with you, Miss Whoever-you-are? You’re chicken. You’ve got no guts. You’re afraid to stick out your chin and say, “Okay, life’s a fact, people do fall in love, people do belong to each other, because that’s the only chance anybody’s got for real happiness.” You call yourself a free spirit, a “wild thing,” and you’re terrified somebody’s gonna stick you in a cage. Well baby, you’re already in that cage. You built it yourself.
One of the more serious films on this list, this untraditional romantic comedy follows two lost souls as they stumble upon their love for each other.
She’s flighty and confused, he’s bored and losing hope. But no matter how hard it is for these two crazy kids to get there, at the end of the day, this film lets us believe that in our own way, we are all worthy of being loved.
7) The Wedding Singer (1998)
Sammy: If you find somebody you can love, you can’t let that get away.
This movie taught us what a perfect church-kiss looks like and gave us the soundtrack to our wedding photo album DVD. Also, Billy Idol is in it, and he’s fabulous.
And as far as the ending’s grand romantic gesture goes: the singing is bad, the lyrics are cheesy, and it’s still the most romantic song to be featured in a rom-com.
8) The Proposal (2009)
Margaret Tate: What am I allergic to?
Andrew Paxton: Pine nuts, and the full spectrum of human emotion.
A modern romantic comedy where neither of the characters is dumbed-down for the sake of plot, Margaret and Andrew are simultaneously funny and frustrating as they go from faking a proposal to falling in love.
Also, their chemistry is on fire in this film. So yes, we do believe that within the span of a weekend he went from hating his boss to proposing to her.
9) Clueless (1995)
Cher: Excuse me, but I have donated many expensive Italian outfits to Lucy, and as soon I get my license, I fully intend to brake for animals, and I have contributed many hours to helping two lonely teachers find romance.
Josh: Which I’ll bet serves your interests more than theirs. You know, If I ever saw you do anything that wasn’t ninety percent selfish, I’d die of shock.
Cher: Oh, that’d be reason enough for me.
Based on a book by one of the OG rom-com queens herself, this 90’s adaptation of Jane Austen’s Emma features one of Austen’s feistiest and most controversial heroines, and like the original material it’s based on, Clueless doesn’t shy away from exposing its heroine’s faults.
Cher is an anomaly of contradictions: smart, but ditzy; selfish, but giving; bratty, but genuinely sweet. It’s these contradictions, like Austen’s own Emma, that make us love her, and help us understand how a respectable, nerdy undergrad like our hero, Josh, could fall for his complicated, but ultimately kind-hearted teenage step-sister. Incest aside, it’s really very sweet. Oh, the 90’s… As if.
10) When Harry Met Sally (1989)
Harry: I came here tonight because when you realize you want to spend the rest of your life with somebody, you want the rest of your life to start as soon as possible.
Finally: A romantic comedy where friendship and respect are at the core of a relationship. How beautiful is that?
In many ways, When Harry Met Sally is the mother load of romantic comedies because it popularized many of the rom-com tropes we now take for granted: characters meet and hate each other, only to later begrudgingly become friends and eventually fall in love.
This classic rom-com is so beloved because it’s also so realistic. Love is hard, and messy, and confusing, and no, it doesn’t usually all work itself out within the span of three days.
So, perhaps what’s most striking about this beloved film is that we know in our hearts that Harry and Sally are both far from perfect people, but in the end, we know that they are so perfect for each other.
What’s your favorite rom-com to rewatch?
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