If Valentine’s Day really was invented solely to torture single people, one might argue that the entire romantic comedy genre is intended to see them through. Having lived through our share of solo February 14ths, everyone in this office knows the power of feel-good Valentine’s Day movies when you need it.
We put our heads together to come up with our all-time favorite flicks for love day—movies that make us laugh, cry, happy (and sad) tears feel good, and renew our hope in love. So, if you happen to have complete power over the remote control this week, take advantage of one of our 20 favorite films. Warning: not all of them have a happy ending but ain’t love grand.
High Fidelity, 2000.
Because if there’s anything we love more than an optimistic teenage John Cusack with a stereo over his head, it’s a bitter thirty-something Cusack who works at the local record store. This hilarious study of romantic relationships is infinitely quotable, totally relatable, and oh-so-good.
Midnight in Paris, 2011.
This movie will spark your imagination. Follow a charmingly bewildered Owen Wilson as he stumbles through time in the foggy streets of Paris. Did it really happen? Or did he imagine it? Either way, it’s magical and we want to watch it again and again—especially for another glimpse of that guy who plays Hemingway.
This little French film about an insurance boss and his quick typing secretary is one part sports movie, two parts rom-com, and altogether charming. We especially love the fun 60s fashion and whimsical action scenes in this quirky romance.
When Harry Met Sally, 1989.
First they hated each other. Then they were friends… Billy Crystal and Meg Ryan still charm in the godfather of all romantic comedies. This one has staying power.
Breakfast at Tiffany’s, 1961.
Because being broke, quirky, and single in the city has never looked so chic.
Bridget Jones’s Diary, 2001.
If we could only pick one Valentine’s Day movie for the single person, it would probably be this. We get Colin Firth and Hugh Grant. An endless stream of cheeky references to Pride and Prejudice. And Renée Zellweger doing every single stupid thing we’ve ever done or thought about doing ourselves. Bridget Jones, you are the everywoman. And we physically need for things to work out for you.
Our generation’s gamine in the role that made her famous: a shy and charming romantic who mischievously meddles in other people’s love lives. Trés sweet.
That Thing You Do! 1996.
Liv is at her absolute loveliest in Tom Hank’s directorial debut about an innocent group of high school musicians who become overnight sensations.
Sixteen Candles, 1984.
I have two words for you: Jake Ryan. If (like some of the girls in this office) you are somehow too young to have seen John Hughes’ original brat pack movie, consider this one a personal assignment from me. You’ll get to see the film that arguably defined “high school movie”, Anthony Michael Hall at his most adorable, and one of the most classic on-screen kisses of the eighties.
Romantics Anonymous, 2011.
Okay, so this quirky little comedy based on Nick Hornby’s 1998 novel doesn’t end with a dream wedding, but trust us when we say it’s exactly what you need this Valentine’s Day: Hugh Grant at his best in a role that’s meant for him, an adorable kid, and a heartwarming story that will have you believing in love of a larger kind.
The costumes, scenery and dreamy 1950s world of director John Crowley’s film are enough to have us mesmerized. But it’s the innocent love between main characters Ellis and Tony that puts this Oscar-nominated flick on our all-time love list.
The Goodbye Girl, 1977.
This screen adaptation of Neil Simon’s famous comedy is ripe with the playwright’s signature one-liners. Set in gritty 70s New York City, this old school rom-com delivers just what we want (even if we see it coming a mile away). One of Camille’s personal faves!
The Mirror Has Two Faces, 1996.
This 90s comedy charms with the unlikely pairing of Barbara Streisand and Jeff Bridges as lonely Columbia professors. When Barbara’s sister takes the initiative to answer Jeff’s personal ad, the two find themselves quickly falling into a very unconventional relationship. Produced and directed by Streisand herself, this movie has a great message about beauty for women. And hey, I don’t know about you but I want to live in a world where Babs can turn down a desperate Pierce Brosnan. #anythingispossible
Put on your PJs and break out the red wine and popcorn. This movie is pure escapism in the best way possible. Based on the classic novel by Thomas Hardy, this period drama stars Cary Mulligan as the beautiful and headstrong, Bathsheba Everdene. She has three suitors to choose from and (gasp) she even makes a few mistakes along the way. We love the story for its message of perseverance and the movie for the gorgeous English backdrop.
Annie Hall, 1977.
Woody Allen’s comedy starring himself and Diane Keaton goes well beyond the “rom-com” category it may have created. This is pure vintage Woody: neurotic, smart, dialogue-charged, and very funny. If you haven’t seen this 1970s classic, we think you’ll recognize the movie’s influence on so many of the things you already love (think Sex and the City, When Harry Met Sally, and even Ferris Bueller’s Day Off).
10 Things I Hate About You, 1999.
The last of the great 90s high school movies, this is one cable classic we simply can’t turn away from on a Saturday morning. And why should we? It’s got a young Heath Ledger, all the high school archetypes we know and love, and it’s even adapted from a Shakespeare play. So, it’s kind of educational, right?
We loved her as Felicity, and well, for girls of a certain age Kerri Russell is forever. This time she’s in her thirties, stuck in a boring job and a bad marriage. It’s up to creativity, love, and luck to help her find a way to start life anew.
Pirate Radio (The Boat That Rocked), 2009.
From the same gang who brought us Love Actually, this feel-good British comedy follows a ship of rogue deejays off the coast of England. We dare you to not smile throughout their voyage (which encounters the loss of virginity, a hippie wedding, and a love-fueled game of “chicken”) all with joyful silliness (and an amazing soundtrack to boot.)
The Princess Bride, 1987.
Rob Reiner’s VHS masterpiece is basically part of our collective ID at this point. To Will Smith (who once famously said you cannot be both sexy and funny at the same time) I present to you a young Cary Elwes. Touché.
If you haven’t seen this classic by now, then please add it to your must-watch list. A young bubbling Hugh Grant and a stunning Andie MacDowell (who just gets better with age) pair up in this hilariously romantic comedy. You’ll laugh, cry, cringe, and swoon.
There is so much emotional tension in this movie so prepare yourself. The beautiful Tita (Lumi Cavazos) is forbidden to marry her true love, Pedro (Marco Leonardi) since tradition dictates (as the youngest in the family) she must care for her mother. So, in a very anguishing twist, he marries her older sister, Rosaura (Yareli Arizmendi) even though he still loves Tita. Of course, you can only imagine the tension that ensues as a result. Just watch it and see what unfolds.
The classic Shakespearean tale has been adapted many times but none of them bring it into a modern context quite like Australian director, Baz Luhrmann. The version of the tragic story has Romeo (Leonardo Dicaprio) and Juliet (Claire Danes) living in a post-modern city named Verona Beach where the Capulets and the Montagues are two rival gangs. The pair meet when Romeo crashes the Capulet’s lavish masked costume ball (the fish tank scene is iconic!) and the rest is history. Not only will you love this contemporary adaptation but you’ll also love the soundtrack (this Radiohead song is imprinted to memory) and the costumes (Romeo’s Hawaiian shirt is a Halloween favorite).
Another classic that was given a modern update is Great Expectations. There have been many director’s who’ve attempted to improve upon this iconic tale but this one really stands out. Why? Well, first of all, the protagonists are a young Gwyneth Paltrow and Ethan Hawke. Secondly, the green with envy costume color scheme throughout the film is legendary (90s Donna Karen, say no more!). And once again, you will listen to this soundtrack on repeat and add it to your favorite albums of all time—we promise!
We couldn’t compile a list of top Valentine’s Day movies without including this recent romantic (and tragic!) flick with everybody’s heartthrob, Timothée Chalamet. The tension between the two is unbearable at times but try and watch this movie without experiencing goosebumps all over your body. This story of young love and self-discovery is incredibly moving and devastatingly heartbreaking but it’s one we will watch over and over for its stunning cinematography and soundtrack (Sufjan Stevens nailed this one!).
Another movie that proves love can appear in unexpected places and it can be, well, complicated. This was the case for Therese Belivet (Rooney Mara) who falls for the captivating Carol (Cate Blanchett) after seeing her at a 1950s Manhattan department store. Of course, you guessed it, the two women form a bond that quickly becomes a love with complicated consequences.
This post was originally published on February 12, 2018, and has since been updated.
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