Though the romantic comedy has long been considered by mainstream media and pretentious cinephiles to be positioned at the lowest level of cinema (especially with the coinage of the term “chick flick”), it’s a genre that has been an essential and delightful part of popular culture for over a century. So, here I present the best of this ridiculously fun genre to help you bask in the Valentine’s Day spirit, whether you’re spending it with yourself or someone else.
1920s: seven chances
Even if you’re not partial to silent films, this is such a fun watch. It stars the iconic Buster Keaton and follows his character Jimmie who tries to find a wife in ONE day to meet the stipulations of his late uncle’s inheritance.
Available to stream on YouTube
1930s: the awful truth
A gem from Cary Grant’s early career, this lighthearted movie follows a divorced couple who begin to reconsider their separation as they both continuously sabotage each other’s new relationships. With a story that’s somehow ageless and ahead of its time, this one is a definite classic.
Available to stream on the Criterion Channel
1940s: the shop around the corner
In this enemies-to-lovers classic, Jimmy Stewart and Margaret Sullavan play gift shop employees who hate each other but eventually fall in love through anonymous letters. Sound familiar? That’s because it’s based on the same play that inspired the 1998 film, “You’ve Got Mail.”
Available to rent on iTunes
1950S: ROMAN HOLIDAY
Starring Audrey Hepburn in her breakout role as a runaway princess and Gregory Peck as a dashing American reporter, this film tells the story of an exclusive interview opportunity turning into a whirlwind romance. Between Hepburn’s playful naivete and Peck’s roguish charm, it is simply impossible to not enjoy this movie.
Available to stream on Paramount+ and Kanopy
1960S: THE YOUNG GIRLS OF ROCHEFORT
The only non-English film included in this list, this French musical follows a pair of sisters and their drama-filled romantic endeavors with two suitors (one of which is played by American dreamboat Gene Kelly). Not only are the characters and music enchantingly fun, but it’s one of the most gorgeous movies I have ever seem. I simply couldn’t resist including it.
Available to stream on HBO Max and the Criterion Channel
1970S: HAROLD AND MAUDE
This quirky dark comedy follows a young man fascinated with death as he meets an enigmatic, elderly woman who shows him how important it is to live life to the fullest. I’m not exaggerating when I say this movie is life-changing and has the most beautiful soundtrack ever.
Available to stream on Amazon Prime and Kanopy
1980S: THE PRINCESS BRIDE
An eighties cult classic and one that will make you literally laugh out loud, this film puts an endearing modern spin on a classic fairytale love story.
Available to stream on Disney+
1990S: 10 THINGS I HATE ABOUT YOU
This is my personal favorite film on the list (and truthfully one of my favorites of all time). Adapted from Shakespeare’s “The Taming of the Shrew,” it tells the story of a geeky new kid who enlists the help of the school’s resident bad boy in order to win over two sisters with strict dating rules. Their ambitious plot becomes even more complicated when romantic rivals and real feelings get involved.
Available to stream on Disney+
2000S: HOW TO LOSE A GUY IN 10 DAYS
Overflowing with chemistry and humor, this is easily one of the most beloved rom-com movies of all time. Kate Hudson and Matthew McConaughey play a couple who, unbeknownst to them, both use each other in a ploy to further their careers, which proves to be more challenging than they planned. The pair also recently reunited in an Instagram live to celebrate the film’s 20th anniversary. So cute.
Available to rent on iTunes and Amazon
2010S: CRAZY, STUPID, LOVE.
This star-studded film puts the ‘comedy’ in rom-com. Steve Carell plays a recently divorced father who a playboy, Ryan Gosling, takes under his wing while also trying to woo Emma Stone’s character. And if that’s not enough, it also features a slow-motion sequence of Gosling eating pizza. Just saying.
Available to stream on HBO Max
2020S: PALM SPRINGS
This movie stars Andy Samberg and Cristin Milioti as a duo stuck in a time loop together (with J.K. Simmons in a hilarious supporting role). Forced to attend the same wedding together every day, the initial animosity between the pair slowly turns into romance.
Available to stream on Hulu
From makeover montages to tear-jerking love confessions (and everything in between), there’s a rom-com for you. Take your pick, grab a box of chocolates and get ready for a few hours of the cheesiest, yet most charming, content you’ve ever seen.