The 25 Best Romantic Comedies of All Time

The 25 Best Romantic Comedies of All TimeEXPAND
Touchstone Pictures

Lights. Camera. And, if you're lucky, action.

It goes without saying that the rom-com reigns supreme among girls' nights out, dinner-and-a-movie dates, and lonely Netflixing singles. While we've seen our fair share of heartbreakingly bad love stories on screen, we've also witnessed a good amount that give us hope in happily ever after.

Heat up the popcorn and dim the lights, because we're about to revel in the 25 best romantic comedies of all time.

There's Something About Mary
Maybe one of the grosser romantic comedies out there, There's Something About Mary manages to weave a love story, complete with zipper-penis accidents, sploosh hair gel, and stalking a high school sweetheart. It's also our favorite rom-com for both Ben Stiller and Cameron Diaz.

Groundhog Day
Who hasn't wished for a first date do-over? When a self-centered weatherman played by Bill Murray is stuck living the same Groundhog Day over and over, hilarity and eventually love ensue.

Knocked Up
Maybe it's not your traditional love story, but it certainly got the laughs and heartfelt message across. If ever there was a rom-com that convinced people to wear a condom, this was it. It may also be the only good romantic comedy to star Katherine Heigl.

Clueless
You think Clueless doesn't count as one of the greatest rom-coms of all time? As if. The '90s classic is an adaptation of the even more classic novel, Emma by Jane Austen. This cult favorite is cinematic proof that virgins can't drive, feather boa trim needs to die, and Paul Rudd doesn't age.

As Good As It Gets
Jack Nicholson isn't exactly the first person you expect to see in a rom-com, but his role as a misogynistic writer with crippling OCD countered by a empathetic single-working mother and a financially struggling gay artist gives audiences hope for humanity and mid-life romance.

Amelie
This foreign film favorite introduced American audiences to Audrey Tautou and the French rom-com, which is sort of like the American rom-com except way more indie, way more whimsy, and the Travelocity gnome is involved.

40 Year Old Virgin
Admittedly this Judd Apatow film is more com than rom, making it one of the few love stories that couples can agree on seeing. A coming-of-age film in more ways than one, 40 Year Old Virgin is a film rife with memorable moments: drunken drives for french toast, picking up chicks at bookstores, and, of course, the infamous chest waxing scene.

Four Weddings and a Funeral
British rom-com poster boy Hugh Grant gives his usual endearing performance as a bumbling bachelor, and naturally we and Andie MacDowell give in. Blame it on the glasses, the big floppy hair, or the accent, but there's just something about awkward Englishman that makes American audiences swoon.

One Fine Day
Two single working parents who just so happen to be incredibly gorgeous spend a chaotic day swapping kids and overcoming career obstacles only to find love with each other by the end of the day. It's basically the 24 of rom-coms.

Bridget Jones's Diary
Bridget Jones's Diary is the modern day woman's Pride and Prejudice. It's filled with heartthrobs, hangovers, and horrifically embarrassing moments that would make any lesser woman want curl up in a ball and disappear. Which is perhaps a more accurate reflection of how dating really goes down.

The Wedding Singer
Love stinks. But this '80s-style flashback film featuring Adam Sandler and Drew Barrymore does not. This wouldn't be the first time these two would find love on screen, but it would be our favorite time. And between the Boy George look-alike and the shoulder pads, can you really blame us?

Say Anything
This '80s film starring John Cusack is one of the most memorable rom-coms of all time, mostly for the iconic scene where a trench-coat wearing Cusack stands outside his car with a boombox overhead. What with potential restraining orders and noise violations, we're pretty sure this move wouldn't work in real life. But hey, give it a shot if you like.

 

Never Been Kissed
For every girl that wasn't popular in high school, this movie was for you. A grammar nerd gets her second/only chance at love and we get a chance to see a young Jessica Alba dressed as disco Barbie. Sure Drew Barrymore nearly lands a teacher in hot water over relations with a student, but as with any good rom-com we can overlook the unrealistic plot holes.

It Happened One Night
This 1934 rom-com is not only one of the originals, it's one of the best, winning Academy Awards for best picture, actor, actress, director, and writing and serving as the inspiration for numerous other films throughout the decades.

Princess Bride
The rom-com gets medieval, and we get some top notch one-liners. The Princess Bride is a fairy tale, slapstick, and love story all wrapped in one, making it one of those all-ages films that it is entertaining to everyone.

The Philadelphia Story
What could possibly derail a second marriage? How about the unexpected arrival of your ex-husband and a tabloid reporter? This 1940 film features Katharine Hepburn and Cary Grant making it not just one of the best but also one of the most good-looking roms-coms of all time.

10 Things I Hate About You
Not too many high-school romances made our top 25 list, but this modern adaptation of The Taming of the Shrew certainly makes the cut. Sure the movie wasn't groundbreaking, but it is both endearing and entertaining. In other words, not underwhelming or overwhelming, just... whelming.

Sixteen Candles
How do yo make up for a sweet 16 in which everyone forgets your birthday, a bunch of nerds pay to see your underwear, and everything is overshadowed by your doped-up sister's wedding? By sharing a candlelit kiss with in your bridesmaid dress with the hottest guy in school.

Breakfast at Tiffany's
What woman hasn't dreamed of being Holly Golightly? An eccentric yet glamorous Audrey Hepburn captured the hearts of audiences and the handsome writer who lives in her building. Anyone else craving a croissant in front of Tiffany's?

Love Actually
How many rom-com plot lines can you cram into one feature-length film? At least seven, according to Love Actually. The British bundle package of romance reigns on the list of lovey-dovey date-night films despite having some serious plot holes. Seriously, is no one going to address the fact that Laura Linney disappears at the end?

Annie Hall
When a neurotic Wood Allen finds and loses love with a carefree Diane Keaton, we get a film that covers all the dating basics: having conversations about exes, running into exes, and letting past experiences with exes ruin your current relationship.

While You Were Sleeping
Only in a rom-com would pretending to the be the fiance of a comatose patient, then ultimately falling in love with his brother, and having everything be okay with that be considered fine. Just like Paul Rudd, Sandra Bullock does not appear to age.

You've Got Mail
If ever there was a romantic comedy that dated itself, it's You've Got Mail. When two book- worm business owners found love via AOL email we couldn't help but fall with them. Of course it doesn't hurt that said book worms just so happen to be the always likeable Tom Hanks and
rom-com queen Meg Ryan.

When Harry Met Sally
Speaking of the rom-com queen, her claim to the thrown was staked alongside Billy Crystal in a film that asks the question, "Can men and women just be friends?" The answer is apparently no, no they can't.

Pretty Woman
We have to give our number-one spot to the hooker with a heart of gold. Julia Roberts and Richard Gere had such chemistry on camera that they eventually repeated their onscreen romance with the less-than-stellar Runaway Bride. But we won't let that tarnish the memory of karmic Beverly Hills shopping excursions, secretly doing floss in the bathroom, and Prince karaoke sessions in the tub.


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