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The 20 Saddest Movies of the 21st Century, From ‘Amour’ to ‘Million Dollar Baby’

Break out the hankies and prepare to feel the full depths of human pain — as made possible by the magic of cinema! — thanks to some of the decade's most wrenching, heartbreaking, and just plain sad films.

As much as we all love a stunning tracking shot or an impeccably stylized thriller, even the most discerning cinephiles have to admit: Sometimes, you just want a good cry. Often it’s the most gut-wrenching movies that remain in our collective cultural memory the longest; “Sophie’s Choice,” “Terms of Endearment,” and “Schindler’s List,” to name just a few. Even in an age when auteur-driven driven sci-fi and superhero franchises reign supreme, Hollywood will always love a good old-fashioned tearjerker. Which is why we thought it necessary to single out some of the saddest movies of the century — so far.

Though it might sound trite, one doesn’t have to give up gorgeous cinematography or a tightly-wound script in order to be moved. Not only do the films on this list find beauty in the most heartbreaking of human experiences, but they represent some of the brightest auteur filmmakers working today, including Ira Sachs, Isao Takahata, and Asghar Farhadi. It wouldn’t be complete without a few blockbusters as well; studios have long perfected the art of making audiences weep.

From “Brokeback Mountain” to “Amour,” here are the twenty saddest movies (narratives only, at least for now) of the 21st century:

“Amour”

Michael Haneke Amour

“Amour”

“Amour” may be one of the saddest films ever made, but the saddest thing about it is ultimately the fact that it has a happy ending. People were understandably skeptical about a Michael Haneke film with such a disarming title — after all, this is a guy who made a hyper-disturbing meditation on violence called “Funny Games,” and then made it again in case we didn’t get the joke the first time. Unfortunately, however, there’s nothing the least bit ironic about “Amour.” Yes, this confined relationship drama is a lot colder than your average love story. But this sobering portrait, the tale of an old Parisian man (Jean-Louis Trintignant) who’s forced to care for his frail wife (Emmanuelle Riva) after she suffers from a stroke, is profoundly beautiful for its coldness. Hinted at in the startling first scene, this unforgettable film builds to a pure act of mercy, the husband putting his partner out of her misery. It’s a devastating moment, to be sure, but — realistically — it’s also the best possible outcome for a healthy marriage. After helping each other through this life for so long, what better way to honor someone than helping them into the next one? -David Ehrlich

“Brokeback Mountain”

“Brokeback Mountain”

The love affair between Ennis (Heath Ledger) and Jack (Jake Gyllenhaal) is so pure and passionate, but it’s complicated both by each man’s marriage, as well as the strict social confines of the time. Ennis’ love and attraction to Jack is unbridled when two are alone and isolated, but he also struggles with his own sexuality, haunted by childhood memories of the murders of two men suspected of being gay. Although Ennis continues to see Jack on fishing trips, he is gruff with both Jack and his family, and eventually his marriage ends in divorce. Year later, when Ennis learns that Jack has died, he finally lets his emotions slip when he visits Jack’s bedroom and finds a shirt from their time on the eponymous Brokeback Mountain. He buries his face and lets a torrent of emotions break through, weeping into the shirt and bringing the audience to tears. -Jamie Righetti

“Fruitvale Station”

“Fruitvale Station”

Oscar Grant was another young African American man we remember through grainy, removed cell phone video of his death at the hands of the police (the officer was later found guilty of involuntary manslaughter). That was before “Fruitvale Station,” based on a remarkably simple premise — the last day of Grant’s life leading up to his tragic homicide on the BART platform that evening — delivered with remarkable emotional complexity from a then-27-year-old director, Ryan Coogler. We see Grant (Michael B. Jordan) as a young man struggling to be a better one, in a realistic portrayal of his up-and-down relationship with his girlfriend (Melonie Diaz), his desperate attempt to get his job back at the grocery store, and even a brief flirtation with selling pot to make ends meet. Coogler and Jordan find humanity and beauty in Grant’s desire to be a good son, father, and provider. Before Black Lives Matter became a movement, this was a film that refused to let a grainy video of death be how this life was remembered. When Grant’s real-life family gathers at the end of the film, his daughter having grown four years, it’s a devastatingly, powerful moment. -Chris O’Falt

Still Alice

“Still Alice”

The indication that something is very wrong with Alice (Julianne Moore, in one of her best roles in a career principally composed of “best roles”) comes care of an ironic twist: the linguistics professor can’t remember a word. It’s a small thing, a tiny bump, a brain trick wholly relatable to everyone, but Alice — and us, the audience — instantly know it’s indicative of so much more. Richard Glatzer and Wash Westmoreland’s finely tuned drama follows Alice and her family (including Kristen Stewart as her quietly heartbroken and immensely dedicated daughter) as they attempt to navigate a world suddenly ruled by her early-onset Alzheimer’s, a disease that damages all of them in very different ways. It’s the care and grace that every member of the production put into it — Moore herself made it a priority to spend time with those effected by the disease and studied for months, co-star Kate Bosworth was clear with Glatzer and Westmoreland how personal the material was to her, and Glatzer himself was suffering from ALS during shooting — that set “Still Alice” apart and makes it hurt so deeply, because it hurts so truthfully. -Kate Erbland

“Keep the Lights On”

“Keep the Lights On”

One mark of a great film is a scene so raw and unexpected that it stays with you for years, and Ira Sachs’ films are filled with them. For his heartbreaking mid-career feature, the New York-based filmmaker drew from personal experience to tell a story of a man left shattered by his partner’s debilitating drug addiction. Sachs delivers one of the most excruciating love scenes ever put to film; Erik (Thure Lindgardt) holding Paul’s (Zachary Booth) hand as he is pounded from behind by a stranger. Addiction runs rampant in some gay communities, but Sachs is far too nuanced a filmmaker to ever make an obvious “issue” film. Like his equally stunning “Love Is Strange,” “Keep the Lights On” is about the pain of romantic love and its inevitable disappointments. It’s not a fun story, but it’s a profoundly brave one. -Jude Dry

Blue Valentine

“Blue Valentine”

There’s a sad sense of inevitability to how Dean (Ryan Gosling) and Cindy’s (Michelle Williams) love story crumbles. The slow-motion dissolution of both their marriage and their family happens as they realize it. It’s two people narrating the decline of a relationship, almost powerless to stop it from happening. All of this would be devastating enough to watch unfold, but Derek Cianfrance’s film bounces back and forth between present and past, showing how the two got together. To see genuine affection in sequences like Gosling’s ukelele serenade curdle into twin silos of sorrow of self-doubt is a crushing downward spiral. “You Always Hurt the One You Love,” he sings in that moment of handheld pre-trouble bliss. It’s all the more gutting to know that these two knew it all along. -Steve Greene

“The Tale of the Princess Kaguya”

“The Tale of the Princess Kaguya”

When it comes to movies adapted from ancient folklore, it’s never wise to hold out hope for a happy ending — the storytellers of yore weren’t quite as gentle as the movie executives who followed in their wake. In other words, people raised on Disney movies might not be prepared for what’s in store for them at the end of Isao Takahata’s “The Tale of the Princess Kaguya,” which is based on a 10th century Japanese legend and builds to a degree of emotional devastation unseen in any animated film this side of Takahata’s own “Grave of the Fireflies.” There’s a bittersweet sparseness drawn in to Takahata’s style, but the fairy tale story is so simple and gently told that its finale still manages to sneak up on you. It starts when a humble woodcutter finds a glowing miniature girl in a bamboo shoot, and decides to raise the enchanted child with his wife. Young Kaguya grows into a beautiful young woman whose natural radiance condemns her to a revolting life of royalty. In a fit of frustration, she prays to return to her life on the moon (she’s from the moon, by the way). Tragically, her prayers are answered just as Kaguya has reacquainted herself with the bucolic splendor of her childhood and the warmth she found there, the princess spirited away into outer space with no memory of the love that she’s leaving behind. The film ends with an extraordinary celestial parade, an explosion of color descending from the heavens, but all of that beauty only makes things that much sadder. -DE

“Rabbit Hole”

“Rabbit Hole”

A meditation on grief that never hits a false note, John Cameron Mitchell’s big screen version of David Lindsay-Abaire’s play of the same name (the playwright also penned the screenplay) stunningly dramatizes every parent’s worst nightmare. Nicole Kidman and Aaron Eckhart are the ill-fated Corbetts, a seemingly everyday couple who have lost their young son to a tragic accident — and that it really was an accident somehow seems to make things worse — and who are unable to find solace in each other or various attempts to heal up. As their grief grows, so too does a gulf between them, with Howie Corbett opting to pursue more traditional ways of healing (a group of similarly situated parents, a new friend) while Becca Corbett masterminds a plan to befriend the young man who technically killed their son (a wrenching Miles Teller in his first big screen role). The question looms: what will hurt most? and will it be worth it? -KE

“Moulin Rouge!”

"Moulin Rouge!" Musical

“Moulin Rouge!”

Fox/Kobal/REX/Shutterstock

Director Baz Luhrmann’s third feature — a frenetic, glimmering reverie set in Paris on the eve of the 20th century — remains his most critically-acclaimed, having earned eight Oscar nominations and awards for art direction and costume design. “Moulin Rouge!” also reignited the currently-thriving movie musical genre with its tale of a ambitious, bewitching Satine (Nicole Kidman), who wants to wrench control of her body and talent away from the men in her lives. Most of the film is devoted to planning a theatrical extravaganza called “Spectacular Spectacular,” interwoven with multiple cases of mistaken identity — Satine first assumes that the show’s goodhearted writer, Christian (Ewan McGregor) is a rich duke (Richard Roxburgh) who will only exchange an investment for a night in her bed. She and Christian prove ill-fated soulmates: Satine learns that she has highly-contagious tuberculosis, never tells him, and dies at the end of her lone performance in their beloved production. –Jenna Marotta

“Beasts of the Southern Wild”

“Beasts of the Southern Wild”

Beast it! Benh Zeitlin’s debut is vibrant and joyous, but it’s also terribly sad. All the aurochs and fireworks in the world can’t distract from the fact that, at its heart, this Bayou-set drama is about a little girl learning that her father isn’t immortal and she’ll one day be on her own. Well, not entirely — the Bathtub is a singular community that takes care of its own, even with a great flood threatening to wash it away. Quvenzhané Wallis is heartbreakingly good as Hushpuppy, whose story vacillates between the hyperreal and the fantastical. We’re still waiting for Zeitlin’s follow-up five years later, and we’ll have tissues ready when the time comes. -Michael Nordine

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