The 40 Saddest Movies of All Time

Cinema Paradiso

Cinema Paradiso is a beautifully nostalgic picture not just about the beauty and community of movies, but about the people in our lives that make us who we are. The movie is told as a flashback through the life of a film director who remembers his friendship with a projectionist, Alfredo, in his younger years—who helped him nurture his creativity and love of cinema.

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It’s tough to make a dramedy about something as difficult as a cancer diagnosis, but screenwriter Will Reiser based this script on his personal experiences struggling with the disease. Joseph Gordon-Levitt brilliantly plays Adam Lerner, a young journalist who is diagnosed with spinal cancer and given a 50/50 chance to live.

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Lost in Translation

Sofia Coppola has made a name for herself as an incredible director. Her 2003 romantic comedy-drama features a great depiction of a midlife crisis, told through Bill Murray’s aging movie star, Bob Harris. The film has an incredibly melancholy feel throughout, while still mining moments of levity and humor.

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Steel Magnolias

Steel Magnolias is another tearjerker that balances its tone with plenty of warmth and humor between moments of tragedy. The film follows a tight-knit group of Southern women who band together to help their friend, who starts suffering with advanced complications from Type 1 diabetes. It features a stacked main cast, with stars Sally Field, Julia Roberts, Dolly Parton, Daryl Hanna, Olympia Dukakis, and Shirley MacLaine playing members of the friend group.

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Can You Ever Forgive Me?

Far and away the best Melissa McCarthy performance in years, this biographical drama is based on the life of Lee Israel, who became infamous in the literary world when she confessed to writing and selling fake letters by famous authors to make ends meet. The film helps you empathize with Israel’s motivation behind the crimes, but it’s still unflinching in showing the harm of her actions to those she conned. Her dynamic with friend and forgery conspirator Jack—played brilliantly by Richard E. Grant—is the beating heart of the film.

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Into the Wild

Into the Wild is based on the John Krakauer book about the true story of Christopher McCandless. He was an adventurer who died after hitchhiking to Alaska, where he attempted to live off the land in an abandoned bus near Denali National Park. The film is one of Sean Penn’s best directing accomplishments. He found great images in the wilderness and from McCandless’ early life, in addition to guiding the performances by the cast—especially a young Emile Hirsch as the lead—very well.

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Manchester by the Sea

It’s difficult to show depression in an authentic and humanizing way on-screen, but Manchester by the Sea deftly tells the story of a grieving man who suddenly has to care for his teenage nephew after his brother’s passing. Every character is achingly well-written and brought to life by their respective actors.

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Remember the Titans

The Banshees of Inisherin

The Banshees of Inisherin shows one of the most extreme friend breakups ever put on film. Plus, it serves as a reunion of Colin Farrell and Brendan Gleeson with director Martin McDonagh, following their brilliant lead roles in 2008’s In Bruges. On a remote Irish island in the 1920s, Farrell’s sweet, but dull Pádraic is devastated when his longtime drinking buddy Colm (Gleeson), suddenly refuses to talk to him. Throughout it all, McDonagh expertly balances moments of emotional rawness and pure laughs.

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While you may think that Midsommar is just a straightforward horror film, Ari Aster blends terrifying images, moments of dark humor, and gutting tragedy into a wholly unnerving film. The movie sees Florence Pugh’s character, Dani, travel to a remote Swedish commune—and antics ensue. There’s a feeling of tragic inevitability in the film’s events as Dani, her friends, and her distant boyfriend, Christian, seem powerless to escape from the increasingly disturbing cult.

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Simply one of the best coming-of-age stories in recent years, Barry Jenkins’ breakout film takes us through three different periods in the life of a gay Black man coming to terms with his identity. Moonlight managed to simultaneously feel deeply intimate and also profoundly resonant to many viewers. If you haven’t seen the film since it won three Oscars, it’s absolutely worth the rewatch.

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Son of Saul

This war drama, which is set in Auschwitz, is unflinching and profound without reducing the real events it depicts to melodrama. The stars Géza Röhrig as Saul Ausländer, a member of the Sonderkommandos—which were work units made of death camp prisoners who had to clean gas chambers and retrieve valuables from corpses of those killed in them. Most of the film stays in a close shot on Saul as he seeks to give a young gas chamber victim a proper Jewish burial, which is a haunting cinematic depiction of his growing numbness to the horrors around him.

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Dead Poets Society

In The Mood For Love

Wong Kar-wai’s moving and tragic romance follows two neighbors who eventually learn their spouses are having an affair with each other—so they try to begin a relationship of their own. The film is both sweeping and intimate, with beautiful musings on isolation, longing, and missed chances that still resonate today.

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The Florida Project

This indie drama, which is set in a budget motel near Disney World, is expertly crafted to hit you with a huge range of emotions. Brooklyn Prince’s amazing performance as six-year-old Moonnee gives us an innocent point-of-view of her character’s young single mother, who is struggling to make ends meet and stave off homelessness. Still, Moonnee finds tons of fun during aimless summer days at the Magic Castle motel.

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Love Story

Love Story is a foundational romantic melodrama, adapted from the Erich Segal novel of the same name. Ali McGraw and Ryan O’Neal play college students from differing backgrounds who fall in love—and soon face tragedy just as their marriage is beginning. This film probably inspired some of your favorite romantic comedies and dramas. Adjusted for inflation it’s one of the highest-grossing romantic movies of all time.

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Schindler’s List

Based on a true story, Schindler’s List follows the life of Oskar Schindler, a German businessman and member of the Nazi party, who utilized his factory in Poland as a means of rescuing over one thousand Jewish refugees from the Holocaust. Directed by Steven Spielberg and featuring performances from Liam Neeson, Ralph Fiennes, Caroline Goodall, and Ben Kingsley, the film is a remarkable testament to how humans to commit both utter atrocities and remarkable sacrifices.

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Requiem for a Dream

Often ranked as one of the most disturbing movies of all time, Darren Antonofsky’s portrait of four people struggling with drug addiction in Coney Island is certainly not for everyone. However, the film’s cinematic and narrative merit in illustrating the distorted borders of one’s addiction and reality becomes increasingly poignant as their struggles advance.

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Brokeback Mountain

Ang Lee’s gorgeous romantic western about two cowboys in love on Brokeback Mountain was a prime candidate for Best Picture in 2006 (it lost to Crash, which we won’t talk about). The poignant story stars Heath Ledger and Jake Gyllenhaal as closeted men in a decades-long relationship. Their passion for each another grates against the unforgiving era in which their love was founded, and ultimately, it’s that passion that tears the two apart, resulting in a tragic end for nearly all involved.

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My Girl

A childhood classic for many, My Girl features Anna Chlumsky as Vada, a young tomboy with a deceased mother, as she navigates her life as an 11-year-old alongside her best friend, played by Macaulay Culkin. The film is both heartwarming and morbid, displaying Vada’s innocently obsessive relationship with death through her father’s home practice as a mortician.

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Headshot of Josh Rosenberg

Josh Rosenberg

Assistant Editor

Josh Rosenberg is an Assistant Editor at Esquire, keeping a steady diet of one movie a day. His past work can be found at Spin, CBR, and on his personal blog at


Temporary Editor, Partnerships

Jacob is a Temporary Partnerships Editor at Hearst based in Queens, New York with his partner and cat Tiger. He loves learning and writing about Film and TV, Video Games, and the weird histories of unexpected subjects.

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