Valentine’s Day is a time to celebrate love in all its many forms. And more than anything, we love movies. So, this Valentine’s Day, we’ve put together a list of some of the best movies that celebrate love, for you to enjoy this V-Day. Whether you’re celebrating on your own, with a partner, or in a group, these movies will make your cold February nights even more heartwarming.
14. Notting Hill (1999)
Notting Hill comes across like a rom-com Mad Lib. Hugh Grant. Julia Roberts. Two people from entirely different worlds. A meet-cute. A second-act break-up. And a romantic, soaring, third-act monologue. But here’s the thing: if it’s not broke, don’t fix it. Every piece of the movie is firing on all cylinders. And those pieces come together to make it an extremely delightful romantic comedy. Some may feel tempted to describe Notting Hill as a guilty pleasure. But if enjoying a fantastic movie makes you guilty, then lock me up and throw away the key. Just be sure to leave Notting Hill playing on the other side of the bars, like how they made Hannibal Lector watch that televangelist.
13. Bull Durham (1988)
The first of two sports movies on our list, Bull Durham stands up as one of the best romantic comedies. The film stars Kevin Costner plays “Crash” Davis, a veteran catcher on his way out of the professional leagues. Opposite him, Tim Robbins plays “Nuke” LaLoosh, a young up and coming pitcher who has the stuff to make it in the majors. And their shared love interest: Susan Sarandon as Annie Savoy, a baseball groupie. The plot of the film follows Davis and Savoy trying to help Nuke get past his personal limitations and find his full potential. But what makes Bull Durham truly great is the setting. The movie takes place in the world of minor league baseball, something we don’t see in movies too often, let alone in romantic comedies.
12. Say Anything… (1989)
Let’s be honest for a second: The grand romantic gesture isn’t cute. It’s creepy. And the romantic comedy, more than any other single entity, is responsible for convincing us that it’s actually acceptable and not grounds for a restraining order. But be that as it may, the movies aren’t supposed to be depictions of reality. They’re supposed to be heightened and dramatic recreations of it. So, in that context, Say Anything…rules. In real life, standing outside of your ex-girlfriend’s window with a boombox would be grounds for arrest. But that doesn’t mean we can’t think it’s cute and romantic when we see it in Say Anything….
11. Pride and Prejudice (2005)
There are few scenes that conjure up as much emotion as Kiera Knightly and Matthew Macfadyen standing in the rain. Pride & Prejudice is one of the most well-known romantic stories of all time and has been adapted twelve times, as well as a number of other, loser, adaptations ranging from Bridget Jones’s Diary to Pride and Prejudice and Zombies. But Joe Wright’s version is a story uniquely focused on young love. It’s about feeling a groundswell of love and emotion for the first time, and not knowing what to do with it. It is certainly an over-the-top costume drama. But it is also a raw, powerful, and true account of what it feels like to be in love for the first time.
10. Harold and Maude (1971)
I remember the first time I saw Harold and Maude. I was a pre-teen who was interested in movies, and my parents would often share movies with me that they enjoyed and thought I would like too. And I’m here to tell you, Harold and Maude is weird. But I’m also here to tell you that I love weird movies. The dark comedy follows Harold Chasen (Bud Cort) who is fascinated with death, and who rejects the idyllic suburban life. Harold meets, befriends, and slowly begins a romantic relationship with a 79-year-old woman named Maude (Ruth Gordon). Maude is a concentration camp survivor who knows she is near the end of her own life. Through his relationship with Maude, Harold learns to appreciate his life and live life to the fullest.
9. Something’s Gotta Give (2003)
A little movie starring Jack and Diane. Nancy Meyers’ supremely charming romantic comedy about love late in life shows that it doesn’t take a cast of bright-eyed young ingenues to sell love on the silver screen. Of course, Diane Keaton and Jack Nicholson are both talented enough actors to carry a movie on their own. But putting them together in one movie, beautifully styled with Nancy Meyers’ glistening aesthetic, makes Something’s Gotta Give something like a romantic Avengers. Throw in Keanu Reeves, Amanda Peet, Frances McDormand, and Paul Michael Glaser, and you’ve got a movie that will age like a fine wine for decades to come.
8. Crazy Rich Asians (2018)
More than any other movie, Crazy Rich Asians is responsible for the recent comeback of romantic comedies in mainstream movie making. Recently, movies that look like a lot of the titles on this list have gone by the wayside. Movie studios seemed to be following that time-honored Hollywood tradition best summed by Justin Timberlake in The Social Network. Thus, audiences have been treated to an onslaught of superheroes and shared universes. But Crazy Rich Asians demonstrated that, when they’re done well, audiences are still as interested as ever in well-made stories about self-worth and human connection.
7. It Happened One Night (1934)
This movie is the one that’s most likely to show up on other people’s lists of best romance movies. And that’s because It Happened One Night is the movie that is most often pointed to as the progenitor of all romantic comedies. But putting that aside for a minute, It Happened One Night is a supremely enjoyable film. Frank Capra’s simple film making style puts the performances front and center in the movie. And Clark Gable and Claudette Colbert take full advantage of that opportunity turning in a series of beautiful interactions that reverberate through cinematic history for all time. It Happened One Night isn’t a must-watch because it was the first romantic comedy. It must be watched because it was so good, that filmmakers felt compelled to create an entire genre of film inspired by it.
6. My Big Fat Greek Wedding (2002)
My Big Fat Greek Wedding is a weird movie. If you told someone born after 2000 that it was a sleeper hit that earned $368.7M on a $5M budget, I doubt they’d believe you. Somehow, My Big Fat Greek Wedding is both one of the top romantic comedies of the 21st century and a movie with basically no cultural footprint. It’s an Academy Award nominee that audiences flocked to in droves for six months! And there’s a reason for that. It’s terrific! It’s a quirky, hilarious, and deeply personal film that is as good today as it was in 2002.
5. 10 Things I Hate About You (1999)
As far as modern Shakespeare remakes go, it’s a mixed bag. Some are great, like The Lion King. Some are not so great, like the new “live-action” Lion King. But that’s what happens when you’re the most prolific writer in English language history. 10 Things I Hate About You is an update of Shakespeare’s Taming of the Shrew. But, like all memorable Shakespeare updates, it makes a strong stylistic decision. Rather than turn the characters into lions, 10 Things I Hate About You makes the story a high school romantic comedy. It’s the kind of thing that sounds like it wouldn’t work on paper at all. And yet, not only is it a great movie, it might be one of the best* Shakespeare adaptations in recent memory.
*Like, the ones where they don’t use the original script. That’s a whole different thing. We can’t get into it right now. This article is about romance movies.
4. Breakfast at Tiffany’s (1959)
Audrey Hepburn is an icon. And her role as Holly Golightly in Breakfast at Tiffany’s is undoubtedly her most iconic. Her look in the film alone is iconic enough that it conjures up all the feelings the movie wants you to have. Hepburn’s performance as the eccentric, naive Golightly became the exemplar for female leads in rom-coms. And while your mileage may vary on whether or not that’s a good thing, it’s inarguable that the film itself, and the performance specifically, are stunningly brilliant.
3. Some Like It Hot (1959)
Some Like It Hot has everything you might want in a classic romantic comedy. Marilyn Monroe? Check. Guys dressed as women to sneak their way into an all-female band? Double-check. Hijinks that ensue after two musicians accidentally witness a mob hit and have to go on the run to avoid getting killed themselves? Check, check, check. Some Like It Hot is as unpredictable and funny as it was when it was first released. And that’s in no small part because it gives Monroe space to flex her comedy muscles instead of just asking her to stand around and look pretty.
2. Jerry Maguire (1996)
I’m not sure if Jerry Maguire is the most quotable movie of all time. But if you threw it out as a guess on “Family Feud,” I’d clap and say “good answer.” There are indeed a lot of lines in Jerry Maguire that have completely permeated our communal lexicon. But perhaps more impressive is the fact that there’s not a single bad piece of writing in the entire movie. Howard Hawks said that a good movie is one with “three good scenes and no bad ones.” If that’s the case, no one who’s seen it can possibly argue that Jerry Maguire is anything other than a very, very good movie.
1. When Harry Met Sally… (1989)
It’s disingenuous to call When Harry Met Sally… anything other than a masterpiece. It’s a movie whose scope is as broad as a lifetime and the entire human condition, but as specific as a few days in the lives of two people. It’s charming, honest, relatable, and entirely sincere. There’s not a false note in the entire film. Billy Crystal delivers a side-splittingly hilarious as Harry. And Meg Ryan’s unselfish commitment to Sally’s character is a masterclass in acting. Even when it’s being showy (for example, a one-shot telephone conversation that had to be filmed on three different sets at once) it manages to be understated. There is no praise too high for what is, inarguably, the perfect rom-com.