Wednesday Listicles: The Greatest Romance Films Of All Time

Ah, Valentine’s Day. A time when everyone in a relationship celebrates their love, everyone single wishes a fiery death to those in a relationship, and everyone who sits in a cynical state year round considers it just another made-up holiday to make us buy things. I tend to lean towards the third group, but there is a catch. Valentines, romance, and all the schmaltz may be a little too much for me, but if there’s one thing I can get onboard with, it’s a good romance story. I may be cold and cynical, but give me a good romance film, and I’m happy. Which is why today, in honor of Valentine’s Day, I will be giving you all yet another list off of my All-Time Greats list: The Greatest Romance Films of All Time

In theory, romance should be an easy genre. You get two moderately attractive people, throw them into a scenario to prove they’re likeable, and give them great dialogue, and bam, your audience is charmed, and probably crying, either tears of joy or depression. There’s even several ways to do it-historical dramas, musicals (usually exclusively romances), and, of course, the romantic comedy, which are so formulaic that they write themselves, but are so charming, you can’t help but smile (seriously: films like Notting Hill and Four Weddings and a Funeral are evidence of the importance of good actors and a good script, no matter how dumb the plots are). And yet, for some reason, they are so difficult to get right. This makes the films that end up moving us and warming our hearts so enjoyable.

One final note that must be addressed before starting this list: for unfortunate reasons, the romance genre, as well as the romantic comedy subgenre, suffers from a healthy amount of bias. Most of the films focus on white, heterosexual couples. As such, this list unfortunately reflects that trend, despite several of my Honorable Mentions attempting to break that trend. If you are someone who was hoping to see themselves reflected on my list, and you don’t fit into the two descriptions, provided, I offer my apologies, and hope that a definitive film overtakes the classics in the near future.

Before we look at the movies that make us feel most human, let me list some honorable mentions. Let’s start with the musicals, which use songs to portray the overall emotion of falling in love, like the tragic-but-epic West Side Story, the biographical rom-com that is Funny Girl, and the silly-but-sweet Singin’ in the Rain. Then there are the romantic tragedies, the films that are romantic in nature, but feature violent, tragic, or mysterious undertones, like Alfred Hitchcock’s steamy-yet-unromantic Vertigo, the sexy criminal thriller than Bonnie and Clyde, and the heart-wrenching Leaving Las Vegas. Animation has had its fair share of love stories, like the stop-motion Anomalisa, the operatic Beauty and the Beast, and the opening scene of Up (which nearly qualified for this list on its own), and recent options include 2012’s Silver Linings Playbook and last year’s La La Land.

Then there’s the films that aren’t quite romances, but have a romantic streak a mile wide, like the adventure film The African Queen, the dramedy It’s A Wonderful Life, the sports epic Rocky, the political rom-com-dram The American President, the “horror” comedy Ghost and the historical epic Forrest Gump. There are some rom-coms that transcend their genre’s clichés, and helped continue the genre’s legacy for almost a century, from the introduction with Bringing Up Baby and His Girl Friday to Moonstruck and As Good As It Gets (I like the ideas more than the actual execution on this one), and 2001’s Amélie (the most adorable film on this list). My main list may not feature a same-sex relationship, but that’s not to say there aren’t any good ones. I may not be a big fan of Brokeback Mountain, but Carol is a stunning and romantic achievement, and this year’s Moonlight has several romantic scenes without being a romance overall. And let’s not forget the rom-coms, for there are many. Some beloved ones aren’t actually that good, and will never be put on this list, like the dumb The Notebook, the dumber The Wedding Planner, and the truly atrocious Love, Actually. But there are others that are much more pleasant, even if they aren’t necessarily “great.” These are films like Just Friends, Ghosts of Girlfriends Past, 13 Going On 30, Crazy, Stupid, Love, Sleeping With Other People, and the so-dumb-but-so-charming Made of Honor.

It’s worth pointing out that there’s tons of films I haven’t seen, like Now, Voyager, Ninotchka, or Pride and Prejudice, and it’s also worth noting that I can see Roman Holiday and The Way We Were sitting on my shelf right now. I can’t see everything, but I’m hoping to remedy that as soon as possible. And finally, there’s the films that would come in fifteenth, fourteenth, thirteenth, and twelfth place-in other words, the films closest to winning me over the way the top films did. The biggest upsets would be the fall of Gone With the Wind and Titanic, two films I truly love in spite of any flaws the two possess. Then there’s-don’t laugh-the joyful realism of Love and Basketball, one of the most adorable romances of all time. And then there’s The Apartment, a wickedly smart satire that builds to one of the most romantic finales I’ve ever seen on film. Any of these films could make it into the list of greats-and have, on other lists, and yet just missed out on my [correct] list. With that all said, let’s look at the Top Eleven (thanks to a tie) Greatest Romance Films of All Time.

10. Breakfast at Tiffany’s (TIE)

Breakfast at Tiffany’s is not supposed to be a romantic-comedy. It’s not even supposed to be a romance. When Truman Capote (one of my favorite authors) wrote it, it was supposed to be a dark drama about prostitution (Pretty Woman followed a similar route to the screen). Hell, one of the two members of the love story was gay in the books, making the relationship impossible! So why does this story end up standing the test of time? Well, there are lots of reasons. The first is probably because the film chose to buck all traditions: instead of having a commitment-phobic man wooed by the perfect woman, here it is a commitment-phobic woman who is wooed by a flawed man. The second is because of the back-up from the technical crew to properly set the mood. Gorgeous dresses, luscious lighting, and one of the most beautiful songs of all time in “Moon River” all combine to help the audience be wooed by the actions on the screen. And the third-and I cannot stress this enough-is that these are just two highly attractive people. There may not be a more gorgeous image to appear on celluloid than Audrey Hepburn as Holly Golightly first walking in front of the Tiffany’s window, but let’s not undersell how gorgeous George Peppard is. I’m honestly not sure which one I’m more sexually attracted to, because that first shirtless scene for Peppard…whoo, boy. It’s an odd story, to be sure, considering it is essentially about an escort and a gigolo who gradually discover human interaction and find love, and it’s obviously problematic the “wacky best friend” in this rom-com is played by Mickey Rooney in yellow-face (I honestly believe everyone involved meant no harm with the portrayal, but I mean…yikes). However, thanks to a sweet script, pretty actors in great roles, and the power of love, this is one of the all-time great romances.

Note: This description applies for the movie, not the still-awesome song of the same name that defies all sense of logic and common sense and is still an absolute delight.

10. An Officer and a Gentleman (TIE)

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This is one of my favorites on the list, if I’m being honest. It’s just so eighties, but in all the right ways. For example, a cheesy eighties love song plays over the entire movie, but it’s done absolutely perfectly, with the song remaining one of the sexiest love ballads in history (“Love lifts us up where we belooooonnnngggggg…”) A Cinderella story with two Cinderellas, the film shows two people in sh*tty situations trying to turn their lives around, and finding hope in each other. Richard Gere gives Zack Mayo a wild card streak, but layers it with a heart of gold. He wants to escape the destructive patterns his father has left for him, and prove himself to be the good person he’s always wanted to be. Meanwhile, Debra Winger is utterly charming as Paula, a young woman who desires to escape from her small town, but will never resort to the prostitution or shady methods that her counterparts take. The two are lost souls, trying to find their last chance at happiness in a world that has abandoned them. And that’s not to mention the side characters that help change them along the way, like David Keith’s ill-fated Sid (the climactic moment involving his character is the most realistic scene of its kind, and it leaves me disturbed to this day), Lisa Eibacher as Casey, and, of course, Louis Gossett, Jr., in a performance that I’m sure inspired both Full Metal Jacket and Whiplash, even if his goals are to help Zack make the right choices in life. Look, every aspect along the way helps the blossoming romance between our heroes thrive, but if you ask me, it doesn’t get more romantic than the finale. The girl may be the one carried out, but make no mistake: these two saved each other. And every person in this world with a soul wept at that scene.

9. Before Sunrise (And The Trilogy)

Technically speaking, this entire trilogy functions as one of the all-time great romances. A real-time romance, with each one taking place on one day nine years apart (and literally shot nine years apart), the series follows Celine and Jesse, played with verve by Julie Delpy and Ethan Hawke, who met on a train and spend all night talking about their lives, their fears, and, of course, their attraction to one another. Each film focuses on love, loss, second chances, and more as we witness realistic conversations between realistic people play out on screen. They may be my all-time favorite movie couple, their love is so strong. Perhaps this is because Delpy and Hawke helped write their own dialogue, making the characters more distinct and closer to their own personalities, helping the audience connect to them. Hawke is an extroverted, egotistical jackass, but he’s highly romantic, and his ego comes from a good place and a desire to create art. Meanwhile, Celine is a guarded, sarcastic dream, never finding herself able to trust anyone, but desiring to feel connected. Both have their flaws, both have their strengths, but these are what help you feel connected to the characters, and help you fall in love. Richard Linklater has made a perfect trilogy of films, each one equally romantic, but if you ask me to pick, I’m going to go with Before Sunrise as the most romantic of them all. Why am I doing this, even if Before Sunset and Before Midnight are arguably better films? Two reasons. One, Sunrise is my favorite of the trilogy. I can’t explain it, it just is. Two, because it’s truly the most romantic one. Sunset deals more with happiness, second chances and fate than it does with true love, and Midnight is more about the work that goes into making these relationships work. However, Sunrise is just the perfect balance. It’s whimsical, it’s pretty, and it’s about the magic of love. True love, the kind that overtakes you the minute you see someone, and makes you approach them on a train and ask them to spend a night wandering the streets of Vienna with them. That’s the kind of love we all want, and that’s the kind of love that we can only get from Sunrise. That makes it the most romantic film in the trilogy, and the most romantic film of all time.

Ed. Note: While Before Sunrise is the most romantic of the trilogy, there is no better moment in any from the trilogy, or most movies in history, than when Celine reaches for Jesse in the taxi in Before Sunset. That moment is one of the greatest of all time

8. The Princess Bride

Ugh, I love this movie so much. Really, who doesn’t? It’s got action, adventure, horror, fantasy, comedy, and, above all, it’s got romance. Robin Wright is absolutely stunning as the farm girl, Buttercup, who becomes a Princess in order to marry the awful Prince Humperdink (Chris Sarandon), despite being in love with the poor farm hand with perfect hair and a panty-dropping British accent, Westley, played to perfection by Cary Elwes, who disappeared years ago. When the two are reunited after a kidnapping attempt, the two do whatever it takes to keep themselves together. Westley delivers romantic monologues, Buttercup exchanges witty barbs, and the fact the whole story takes place in a fairy tale read by a grandfather to his grandson makes the whole thing feel like a story for the ages (which it is). Honestly, try not to feel your heart melt each time that Westley says “As you wish,” and try not to have your breath taken away every time Westley and Buttercup kiss (I’m not sure there’s been a more stunning kiss every filmed than these two). I dare you to. This is the film that makes women swoon, men feel warm inside, and everyone leaves happy. Quite literally, The Princess Bride is a story for the ages.

7. Her

It’s no secret around these parts that Her is, in my opinion, one of the greatest films of all time, as well as being my favorite film of all time. It’s the reason I managed to open myself up to the romance genre, as well as the rom-com itself. It’s just such a charming, intelligent treatise on what it means to love, as well as what it means to be human, in a way that most films can only dream of. The film follows the arc of the average rom-com, from the meet cute to the first encounter to the big fight and so on, but adds a special twist: while Theodore (Joaquin Phoenix) is your average introverted and depressed hero, his love interest, Samantha (Scarlett Johansson), is a Siri-like Operating System. It’s a goofy premise, and in many ways satirizes humanity’s growing obsession with technology. However, that’s not writer/director Spike Jonze’s main focus here: he wants to focus about the pain, the loneliness, the desperation, and ultimately, the magic of falling in love again. It’s the personal type of story that can only come from experience, with Rooney Mara playing a very Sofia Coppola-esque ex-wife that broke Theodore’s heart. This honesty allows the film to freely explore its themes without restriction. It can explore how we connect, how we fall in love, why we fall in love, and how we can come into our own as people. The line of the film is when Amy, played by Amy Adams, states her belief that “Falling in love is just a socially acceptable form of insanity.” We don’t act rationally when we fall in love. We have no control over our actions, or beliefs, or desires. All we know is that this person casts a spell over us, and changes us, most likely forever. And thanks to the beautiful relationship between Theodore and Samantha (as well as hilarious side characters, like “best friend” Paul [Chris Pratt], blind dates and hookups with Olivia Wilde and Kristen Wiig, and a bratty alien child [Jonze]), as well as the world-building going on in this futuristic setting, we are allowed a temporary glimpse inside the universality of our hopes, fears, and beliefs on love.

6. It Happened One Night

The romantic comedy has rarely been done better than 1934’s It Happened One Night. It’s got all the hits: great one-liners, the whole “they hate each other, but love grows” thing, and hilarious performances by Clark Gable and Claudette Colbert. Their cross-country quest so the spoiled and ignorant Colbert can marry another man while the hot-headed chauvinist Gable gets the ultimate scoop is one of Hollywood’s greatest odd couples, as the two exchange insult after insult, and demonstrate once and for all why history’s great love stories are usually two hotheads with sharp tongues: they’re the only person capable of dealing with the other one’s bullsh*t. That’s a harsh way of describing love, but if we’re being honest, that’s really all we want in life: someone who can deal with our crap, call us on it, and tries to make us better, and vice versa. As much as we may dream about it, none of us really want perfect-perfect is so boring. We want the person who will drive us insane, as Gable puts eloquently in the film. While deriding Colbert’s behavior, calling her “insane” and “awful,” he is asked point blank if he loves her. His response is, “[Of course I love her!] But don’t hold that against me, I’m a little screwy myself!” This is one of the most romantic lines in all of film history, thanks to Gable’s delivery and the universality of this statement. Of course, the story is aided by the humor of the situations-the sheet separating the room, the irony of “married life” during their “fight” in the shed, and, of course, the famous hitchhiking scene, which is incredibly arousing and sexy without showing anything more than a calf. If you’re a fan of any rom-com from the past twenty years, from The Proposal to Just Friends to Ghosts of Girlfriends Past, know that the entire relationship between those leads comes from the magic of It Happened One Night, which did it first, and, if we’re being honest, better.

5. Annie Hall

Annie Hall is sort of the anti-rom-com. It’s really not about love as much as it is “How do you maintain a relationship when you’re anxiety and depression slowly leave you numb to love?” It’s not an easy idea to portray, especially not in a comedy. And yet, that’s exactly what writer/director/star Woody Allen accomplishes in his magnum opus. Told in fragments as Alvy Singer scours his memory to figure out where things went wrong, it features surrealist vignettes to try to understand where things went wrong, and why he can’t make relationships work. This includes flashbacks to his childhood reflecting his awkward encounters with the girls in school and the women in his adult life, the fear of meeting your significant other’s family (here represented by the anti-Semitic grandmother literally seeing the Jewish Allen in full Hasidic garb), the moment the honeymoon phase ends by showing Annie’s disinterest, and the complex back and forth going on in your head when you’re trying to flirt (the subtitles at the bottom as they go back and forth is honestly one of my all-time favorite movie scenes). Each take uses the absurdity of the moment to find a universal truth, and it’s a testament to Allen’s talent as a writer and as a director. Of course, it doesn’t hurt when you have someone as magically lovable as Diane Keaton is as the titular Annie Hall. Keaton’s magnetism makes it clear why Alvy falls in love with her, and brings the audience along for the ride. She and Alvy have a realistic relationship, not the fantastically perfect relationship that most movies believe exist. They argue, they break up, they get back together, and they love. In the end, like Her, Alvy accepts that the concept of love is absurd. And yet, despite the ridiculousness of it all, at are core, we need it. And Annie Hall is the film that reminds us of this truth most of all.

4. When Harry Met Sally…

This is the quintessential rom-com. The quirky friends, the witty barbs, the realistic romance, the great performances, the romantic atmosphere…it’s all here in Rob Reiner’s second film on this list, When Harry Met Sally… It’s a film that studies the relationships between men and women, if they are capable of being friends and nothing more (the film posits yes and no at the same time, which would be annoying if the film wasn’t so good), and breaks the main story up with vignettes of elderly couples reflecting on meeting The One. The film carefully maps out the relationship between Harry and Sally over the years, following as they go from enemies to acquaintances to friends to best friends to something more. It’s a very natural flow, and it allows these characters to find out who they are, in order to form a more lasting relationship. We meet these characters with their biggest flaws on display, so that when they begin to fall in love they can mold each other’s flaws for good: Harry’s a depressive, mopey chauvinist who hides his pain with humor, which he can use to cheer up his friends, while Sally is “high maintenance,” which can be seen as obnoxious until she aims it at her desire to run things smoothly. These aren’t deal-breaking flaws we’re seeing: they’re human traits that make these two feel real four our benefit. Of course, it helps that they have the two perfect actors bringing them to life. Billy Crystal has never been better as the dejected-but-cocky Harry, but let’s not kid ourselves-this film belongs to Meg Ryan, who just absolutely wins your heart as Sally. Whether she’s making a long-winded dinner order, turning the art of crying into a comedic tour-de-force, or performing the infamous “Diner Scene,” she gives one of cinema’s all-time great performances as the little blonde firecracker that is Sally Albright. There are hundreds of other reasons to love this movie: the scene where Harry and Sally first get together is so accurate, I’m sure many people have lived it. Harry’s monologue at the end is arguably the second greatest description of love ever put on film (God, it’s so beautiful). And I haven’t even touched on Carrie Fisher! I could continue going on and on about this film, but I don’t think I need to. Because when I say “romantic comedy,” your mind most likely goes here (or to Katherine Heigl). And that’s because this film is the cornerstone of the subgenre, and one of the greatest depictions of the overall genre in all of history.

3. Doctor Zhivago

The best romances are those that last decades, and span the test of time. That’s the case with Doctor Zhivago, David Lean’s follow-up to Lawrence of Arabia. However, while Arabia is the more beloved film, I would argue that Zhivago is better overall. For one, it gives us peak Omar Sharif being wooed by peak Julie Christie, which is a couple for the ages. Placing their relationship against the backdrop of Russian history, showing the oppressiveness of the czar, but watching this lead to a new oppressiveness under Stalin, the film is told in flashback as a KGB general (Alec Guinness) tries to discover if his brother, Yuri Zhivago, a renowned doctor and even more renowned poet, left him with a niece with the love of his life. The story is only known through the “Lara Letters,” a series of poems that Zhivago had written in reference to his love for a woman he’d only briefly met. In all honesty, that’s what makes this passion so powerful: the couple really only has a few minutes of the three and a half hour runtime to spend together, but you remember the passion with which they kiss, and you understand that this love is so powerful, they are willing to spend years (and hours for us) of their lives just trying to reunite, no matter the state of the country that surrounds them. Everything about this film helps make it so remarkably romantic, from the gorgeous cinematography and art direction to the perfect score. I guess this boils down to two things: first, this is the eighth most-seen movie of all time, so there must be a reason it resonates; which leads me to point two-no romance film can be bad when the people are as attractive as Omar Sharif and Julie Christie. I love this movie, as a romance, as an epic, and as an overall fantastic film.

2. City Lights

When you think Charlie Chaplin, you don’t usually think “romance.” However, that’s what makes Chaplin so great-his versatility. He was capable of staging every style of every genre in a way most people could never think possible. Here, he plays with the romantic comedy, placing the Little Tramp, a vagrant with a heart of gold, opposite a beautiful young blind woman. Telling her he’s a millionaire, she tells him her hopes and dreams, including paying rent and having an eye correction surgery that will restore her sight. The Tramp then gets himself into a series of misadventures and physical comedy, ranging from boxing matches to saving a drunken, suicidal millionaire, as he literally risks everything in order to raise the money to make the young girl happy. It’s a silly, touching story, filled with laugh after laugh, but the way it wraps up is no laughing matter. I don’t want to spoil anything, because this finale is the greatest ending to a film ever, but I will say this: there is no dialogue in this film, leaving the actors with only their expressions to tell the story. And they successful perform the greatest piece of acting in all of film history. The last two minutes will make you weep. You will weep openly, and weep loudly. If you don’t think of Charlie Chaplin as a romantic lead, watch this movie, and then watch yourself be proven wrong. This is the greatest rom-com of all time.

1. Casablanca

Yes, this is #1. Obviously this is #1. What else were you expecting to be #1? There is only one romance that stands the test of time, which is beloved by all, which broke all the early rules and set all the future ones. And that film is Casablanca. It is the zenith of the genre, with the ability to make grown men cry. The story of a guy who is given a second chance to win the love of his life, but has to choose between their personal happiness and the future of the world, it creates the ultimate moral quandary. Rick Blaine is the ultimate romantic hero, and that’s in no small part thanks to Humphrey Bogart. Rick is cynical, and cold-he’s given up on love, he’s given up on life, and he’s given up on goodness. He was hurt in the past, and hurt bad, and he’s willing to let anyone do anything without a sense or morality, be they gangster, mobster, or Nazi. When the woman who hurt him, Ilsa (a stunning Ingrid Bergman), walks back into his life with a new man and the plans that could bring down the Third Reich, Rick’s perspective is given the ultimate test. To be honest, every great plot point and cliché from romance movies comes from this. The great one liners and dialogue? Casablanca’s the king (greatest script ever? It’s a conversation). The love triangle? The love interest here is married. The argument that the stakes are too low? What if we make the stakes the fate of the world? Every decision helps to elevate this to the greatest of greats. And it doesn’t hurt that it all builds up to the ultimate act of love the cinema has ever seen. The Airport Scene remains the high point in these types of movies, as giving up everything to make the one you love happy is the ultimate sacrifice, and the greatest act that someone like Rick can make. It’s sort of like the anti-Love, Actually, as everyone here is acting on behalf of others, instead of selfishly. Look, I don’t know what I can add here that will convince you if the thousands of articles on the subject haven’t already. If you aren’t already aware that Casablanca is the greatest love story of all time, that’s on you. But thanks to perfect writing, directing, acting, cinematography, editing, and storytelling, and the ultimate romantic atmosphere, I add my name to the list of critics to say the following: Casablanca is the most romantic of all time, let alone one of the greatest.

I hope you enjoyed this little foray into romance, and I hope you all had a Happy Valentine’s Day. May all your relationships, be they now or in the future, be as loving and romantic as the greats I’ve listed above. Or this story:

And if you want to see the rest of the Sacred Wall’s Greatest Films list, you can click here.

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