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90 Years of Rom Coms: 20 Date Night Movies That Are Actually Worth Watching

Romantic comedy tropes have been played out so much, it's almost pointless to see any new chick flicks. Spoiler alert: The couple almost always gets together in the end. There's usually a final triumphant kissing scene, probably in the rain. And, don't be fooled by the big argument that happens around the 45-minute mark – they'll find a way to work it out by the time you hit the restroom and refill your 32 ounce soda. 

Since romantic comedies have been around for a century, it's easy to see how plot lines can be recycled. But after watching the golden era of the rom com in the 1940s and '50s, it gives a whole new appreciation to the newer flicks that pay homage to the classics. Sure, the meet-cutes and happy endings are typically predictable, but with more complex characters, intriguing scenarios and witty dialogue, romantic comedies can be far from predictable popcorn flicks. 

Although it was a tough decision  – many debates in the office ensued  – we've come up with the 20 best romantic comedies over the past century. The rom com genre can be pretty broad, but we stuck to movies that have a romantic relationship as the focal plot point, with significant humor throughout. 

So instead of wasting your hard-earned money on the latest rom-com at the local movie theater, make your next movie night one at home and rent one (or several) of these classic films. Open a big tub of popcorn, grab some candy and sit in for some rom coms that are actually worth watching.



Bringing Up Baby, 1938

Katherine Hepburn plays spoiled heiress Susan – the original Paris Hilton – who is flighty and scatterbrained but when she takes a liking to Cary Grant's straight-laced Dr. David Huxley, plenty of hijinx ensue. 


It Happened One Night, 1934

You can't help but swoon over Clark Gable, one of the original movie stars. Another trope about a spoiled heriess and a love triangle, etc. but it's the gold standard of all the similar rom coms of the latter 20th century. 



The Philadelphia Story, 1940

This fun, irreverent comedy is revered as one of the all-time classics, with the three biggest stars of the time: Cary Grant, Katherine Hepburn and Jimmy Stewart. 


His Girl Friday, 1940

Oh, to pine after the one who got away. Will Cary Grant's Walter Burns be able to win back his ex-wife, Hildy Johnson (Roasalind Russell?). 



Sabrina, 1954

Audrey Hepburn was the rom com darling of the 1950s and '60s, and her performance in Sabrina proves her worthy of that fame. The chemistry with Humphrey Bogart is dazzling, and watching this film in black-and-white makes it even better. 


Gentlemen Prefer Blondes, 1953

Though this Marilyn Monroe flick is a satire, the blonde bombshell makes some excellent points re: marrying for money and status, and being BFFs with your bling. 



The Apartment, 1960

C.C. Baxter rises in his company by enabling his older and more successful colleagues to use his Upper West Side apartment for extra-marital trysts. What could possibly go wrong?


Any Wednesday, 1966

Manhattan men really liked having affairs in the 1960s, huh? A successful businessman keeps his mistress (Jane Fonda) in an apartment on the Upper East Side. But when she falls for her married boyfriend's younger business associate (got all that?), things get a lot more complicated. 



Annie Hall, 1977

Widely considered the most iconic romantic comedy during the latter half of the 20th century, this Woody Allen flick won the Oscar for Best Picture in 1997. It even beat out Star Wars, so you know it's worth a watch.


What's Up, Doc?, 1972

This screwball comedy stars Barbara Streisand in her first feature film role, and pays homage to the popular screwballs of the 1930s. 



When Harry Met Sally, 1989

"I'll have what she's having." Enough said.


Say Anything, 1989

This John Cusack classic made every girl wish some guy would show up outside of her window with a giant boombox over his head, blaring Peter Gabriel. Or, if you were me, any song by Dashboard Confessional. 



Pretty Woman, 1990

A very wealthy businessman (Richard Gere) falls in love with a tough-on-her-luck prostitute (Julia Roberts). Because of course he does. 


Clueless, 1995

Think we would forget this movie? As if! Poking fun at the original Rich Kids of Beverly Hills still holds up, 20 years later.


You've Got Mail, 1998

This late-90s flick pays homage to the 1930s The Shop Around the Corner, this time with the Internet, AOL and digital annonymity to make things just a little more complicated. Beautiful shots of New York's Upper West Side and Tom Hanks' adorableness make this one worth watching over and over again. Also, big nostalgia points for the "You've Got Mail!" audio message. 



Bridget Jones Diary, 2001

Bridget Jones is the woman inside all of us: Unhappy with her weight, her job and her love life. Throw in a love tirangle with Hugh Grant and Colin Firth, and things really start to get interesting. 


Love Actually, 2003

OK, this is Taylor Swift's favorite movie, so that should give you a sense of what to expect. But somehow the fancy accents and dry British humor works to make these interchanging storylines enjoyable and relatable. 


Forgetting Sarah Marshall, 2008

When Sarah Marshall (Kristen Bell) leaves Jason Segel's character to be with Russel Brand (who basically plays a highly fictionalized version of himself), hilarity, sprinkled with a twinge of despair, ensues. In Hawaii! 



Easy A, 2010

The modern-day comedy based loosely on The Scarlet Letter (and sprinkled heavily with '80s rom com references) tackles the age-old issue of slut-shaming, this time in the 21st century with Twitter and camera phones to make things worse. 


Silver Linings Playbook, 2012

There's a reason this movie was nominated for 8 Academy Awards, and Jennifer Lawrence scored a win for Best Actress. Silver Linings tackles the taboo subject of mental illness with grace, and plenty of laughs. 



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Meet our Writer
Jennifer Geddes
Celebrations Writer

Jennifer Kelly Geddes has hosted Christmas cookie swaps, New Year's open houses, Thanksgiving for 22, and all manner of dinner parties in her Manhattan and Ghent, NY homes.

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