Romeo and Juliet. Tristan and Isolde. Jack and Rose. Why is it that the most iconic love stories in our collective cultural imagination are also the most tragic? Perhaps because these pairings are all subject to something extraordinary: a connection more powerful than convention, and a love that knows no bounds.

But this love should come with a warning label. In addition to bouts of extreme passion and daydreaming, it may also cause despair, destruction and lots of tears — both for the characters and for the spectators.

So, here’s to the lovers entangled in forbidden partnerships. To the underdogs, the rebels and the mismatched duos. The affairs that might not last in the real world, but run their course over the stretch of one beautiful movie.

After all, romantic comedies are good and fun. But if you want a real romantic movie experience, watch a film guaranteed to make you sob from the highs and lows of human experience, all piled up in rapid succession.

This story was originally published in August 2020 and has since been updated.

Past Lives (2023)

The Tearjerker: “What if this is a past life as well, and we are already something else to each other in our next life? Who do you think we are then?”

When New York-based writer Nora is reunited with her childhood best friend from South Korea, Hae Sung, they must confront how they fit into each others’ lives after all this time. Past Lives delves into the antithetical feelings of being happy in your current life, but at the same time mourning the life you used to live, the person you used to be and the different paths you could have taken — especially when it comes to love.

Queen & Slim (2019)

The Tearjerker: “I want a guy to show me myself. I want him to love me so deeply, I’m not afraid to show him how ugly I can be.”

In this Melina Matsoukas-Lena Waithe collaboration, the classic Bonnie and Clyde story gets a total makeover that’s relevant and poignant for the times. Queen (Jodie Turner-Smith) and Slim (Daniel Kaluuya)’s uneventful first date turns traumatic when they encounter a trigger happy racist cop, sending the unlikely couple on the run and on a heartbreaking journey to love. No spoilers, but this film ends exactly the way you hope it wouldn’t — bring tissues.

If Beale Street Could Talk (2018)

The Tearjerker: “I hope that nobody has ever had to look at anybody they love through glass.”

Based on James Baldwin’s novel of the same name, Beale Street tells the story of Tish (Kiki Layne) and Fonny (Stephan James), childhood friends and now sweethearts who want nothing but to get married and raise their soon-to-be born baby together. Life has other plans: Fonny is arrested and thrown in prison for a crime he did not commit. Tish fights an uphill battle to get Fonny released, but the odds are perpetually stacked against him. It’s a terribly sad love story that’s also about the systemic oppression of Black Americans under mass incarceration.

A Star Is Born (2018)

The Tearjerker: “I’ll never love again.”

A Star Is Born has been remade three times prior to Bradley Cooper’s latest version, and yet no one has thought to change the tragic ending. In this version, Cooper’s rocker Jackson falls for an undiscovered songwriter Ally (Lady Gaga), and encourages her to take charge of her music career. But with Jackson’s own star fading, the relationship between him and the rising superstar is doomed.

Brief Encounter (1940)

The Tearjerker: “I’ve fallen in love. I didn’t think such violent things could happen to ordinary people.”

Brief Encounter is heartbreaking in its ordinariness. A housewife (Celia Johnson) meets a doctor (Alec Harvey) during her routine errand run. They fall in love, of course, during that brief encounter on the train. Though she gravitates closer to him and further from her domestic obligations in the weeks that follow, the couple is crushed by their roles.

500 Days of Summer (2009)

The Tearjerker: “People change. Feelings change. It doesn’t mean that the love once shared wasn’t true or real. It simply means that sometimes when people grow, they grow apart.”

500 Days of Summer is the magical realism, imagination-fueled version of something many of us have, or will, go through: The rise and fall of a relationship. After his girlfriend (Zooey Deschanel) breaks up with him, Tom (Joseph Gordon Levitt) parses through the 500 days of their relationship and figure out what went wrong. As Tom finds, the relationship did start off with a big difference in philosophy, though. Summer doesn’t believe in boyfriends, and Tom is a hopeless romantic.

An Affair to Remember (1957)

The Tearjerker: “I really hope you’ve found happiness, and if you’re ever in need of anything, like someone to love you, don’t hesitate to call me.”

The couple in Sleepless in Seattle wasn’t the first to make plans to meet on the top of the Empire State Building. After meeting, and falling in love, on a cruise from Europe and New York, two people decide to reunite on top of the iconic building in six months. Both are engaged at the time. Six months later, Nickie (Cary Grant) arrives promptly to their high-altitude meeting place, but Terry (Deborah Kerr) is injured on her way. How will he find her again?

West Side Story (1961)

The tearjerker: “For here you are / And what was just a world is a star”

In this iconic musical, the story of Romeo and Juliet is transposed to 1960s Manhattan, and set to music. Revision: In this iconic musical, the story of Romeo and Juliet is improved.

This time around, the instant and forbidden love is between Tony (Richard Beymer), an American, and Maria (Natalie Wood), a Puerto Rican immigrant. Maria’s brother is the leader of the Sharks, a Puerto Rican gang that’s sworn enemies with Tony’s gang, the Jets. Over the next few days, the lovers’ rebellion will unleash a tragic chain of events.

The Umbrellas of Cherbourg (1964)

The Tearjerker: “People only die of love in the movies.”

Guy (Nino Castelnuovo) and Genevieve (Cahterine Deneuve) fall madly in love just as Guy is drafted to serve in the Algerian War. And yet, the love that had been so wildly strong fades. She gets pregnant. He’s comes home and marries someone else. Things change. The movie reaches a breaking emotional climax when, years later, the lovers have a chance encounter on a snowy evening back in the town they first met.

The Fault in Our Stars (2014)

The Tearjerker: “You gave me a forever within the numbered days and I can’t tell you how thankful I am for our little infinity.”

Teen movies are known for playing adolescent emotions like angsty harps, but The Fault in Our Stars raised the bar for ravaging its audiences. In the film, two teenagers diagnosed with cancer meet during a support group meeting and start a relationship. They make the most of the time they have together.

The English Patient (1996)

The Tearjerker: “Swoon, I’ll catch you.”

Is it just me, or do all the most epic love stories also happen to be period pieces with amazing costumes? That description certainly applies to The English Patient, the story of an epic romance between a Hungarian count (Ralph Fiennes) and a married Englishwoman (Kristin Scott Thomas). When we first meet Lazslo, though, he’s burnt beyond recognition in a hospital bed in Italy at the end of WWII. Slowly, he tells the story of his extraordinary life to his nurse, Hana (Juliette Binoche), who has a love affair of her own.

Moulin Rouge! (2001)

The Tearjerker: “The greatest thing you’ll ever learn is just to love and be loved in return.”

Granted, Moulin Rouge’s tearjerker of a line isn’t even from the movie. But so much of Moulin Rouge! is borrowed, including the main songs. Christian (Ewan MacGregor) and Satine’s (Nicole Kidman) love story is doomed from the start. But director Baz Luhrrman makes sure that everything that comes before the tragic ending is gleaming with beauty and lavishness.

Chungking Express (1994)

The tearjerker: “Actually, really knowing someone doesn’t mean anything. People change. A person may like pineapple today and something else tomorrow.”

In this heavily stylised film, two cops in Hong Kong fall in love. Kaneshiro falls for the mysterious, trenchcoat-clad Brigitte Lin, and his coworker, Leung, is drawn to the day-dreaming kebab-stall girl, Faye Wong. But in this movie of “could have beens,” the possibility of romance is more exciting than any substantial relationship actually materialising between the pairs.

Titanic (1997)

The Tearjerker: “It doesn’t make any sense. That’s why I trust it.”

When Jack (Leonardo DiCaprio), a drifter with boyish charm, and Rose (Kate Winslet), a 17-year-old socialite, climb aboard the doomed ocean liner, there are two things they don’t know. First, that the ship will sink after hitting an iceberg in the Arctic. Second, that before the ship sinks, they’ll experience an awe-inspiring, life-changing love — the kind, perhaps, worth boarding the Titanic for.

Brokeback Mountain (2005)

The Tearjerker: I wish I knew how to quit you.”

As Ennis Del Mar (Heath Ledger) and Jack Twist (Jake Gyllenhaal) discover, a lot can happen during long nights on the range. Under the big Wyoming skies in 1963, Jack and Ennis fall deeply in love. Over the next 20 years, the men fight to preserve what was once kindled on Brokeback Mountain, but struggle against the oppressive constraints of their marriages and societal pressure.

Up (2009)

The Tearjerker: The heartbreaking five-minute-long opening montage that tells the story of Carl and Ellie’s marriage without words.

Carl’s a grumpy 78-year-old balloon salesman man, closed off to the world since the death of his beloved wife. She passed away before they could take their trip to Paradise Falls, the place where adventure awaits. Rigging his old house up with balloons, Carl’s planning his big exit: a trip to Paradise Falls. But when Carl takes off and finds an over eager Boy Scout has snuck aboard, his grand plans are dashed.

Amour (2012)

The Tearjerker: “Please never take me back to the hospital. Promise…Promise me.”

Most romance movies are about the start of a relationship. Amour, a French drama about a married couple in their 80s, is about the uncomfortable implication in the vow, “‘Til death do us part.” Georges and Anne, retired music teachers, have spent their lives together. After Anne suffers from an attack, her impaired state brings the couple near the bleakest impasse of them all: the inevitability of an ending.

Call Me By Your Name (2017)

The Tearjerker: “Remember, our hearts and our bodies are given to us only once.”

Each summer, Elio (Timothée Chalamet) goes to his family’s Italian villa with his father and mother. In the summer at the age of 17, Elio experiences something we all hope to: sublime, searing, true love, which comes to him in the form of David, his father’s research assistant. After a few weeks of denying the rumblings of attraction, David and Elio come together with an intense craving for oneness, to create something more significant than either of them are individually.

Like Crazy (2011)

The Tearjerker: “What have you been doing?” “Waiting for you.”

Visas, immigration and other impediments to true love are such a drag. When the British Anna (Felicity Jones) and the American Jacob (Anton Yelchin) fall madly in love at the end of their senior year in Los Angeles, Anna violates the terms of her student visa for a few more days with Jacob. Consequently, Anna is barred from reentering the United States. The thrilling, blissful fury of first love struggles with transatlantic pressures in this downright heartbreaking, authentic film.

The Curious Case of Benjamin Button (2008)

The Tearjerker: “I wanna remember us just as we are now.”

In one of American cinema’s more interesting forays into fabulism, Brad Pitt plays Benjamin Button, a man destined to grow “young” instead of old. Born an old man, Benjamin ages in reverse. Benjamin and his his childhood friend, Daisy Fuller (Cate Blanchett), are madly in love. But given their reverse aging trajectories, there’s only a limited time frame in which they can be together.

Forrest Gump (1994)

The Tearjerker: “Why don’t you love me Jenny? I’m not a smart man but I know what love is”

No one can deny the emotional thunderstorm that erupt each and every time you watch Forrest Gump. Forrest (Tom Hanks) takes a whirlwind journey through life as he comes to understand why his low IQ level is an apparent disadvantage, becomes a football star, serves in the American army in Vietnam and, of course, falls in love.

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