The 50 Saddest Movies to Watch on Amazon Prime

Fear of abandonment is at the heart of The Vanishing. Lovers Rex and Saskia are separated on their way to France after the latter vanishes without a trace. For the next three years, Rex dedicates his life to finding out what happened to Saskia in whatever way possible, endangering his own safety in the process. George Sluizer’s chilling psychological thriller shows the evils that curiosity and obsession can bring, and is a uniquely perverse look at the ugly side of truth-seeking.

In Playground, we follow seven-year-old Nora as she navigates friends and school. Through her eyes (and often on her eye level), we witness her and her brother trying and often failing to fit in.

The film is an unfiltered account of their formative years, and possibly a reflection of our own. Commercials and kid-friendly media would have us believe that childhood is simple and pure, but the truth is it isn’t exempt from the major pitfalls of humanity. Children will mimic whatever they see, reasonable or otherwise, and the resulting order won’t always be ideal. Case in point: in the schoolyard, free of adult supervision, Nora and her peers push and tease and harass one another. 

It’s painful but relatable, a microcosm of our own complicated world, and though the film doesn’t shy away from the cruelties of bullying, it’s also filled with moments of empathy and warmth.

It’s heartbreaking to realize that Happening, a film set in 1960s France tracking a young woman’s journey to dangerously and desperately terminating her pregnancy, is still very much relevant and relatable to this day. Around the world, abortion is still inaccessible, if not completely illegal, and women still struggle to lay full claim to their bodies. A lot of girls grow up with pregnancy statistics meant to instill fear, but Happening brings all that to brilliant life in intimate and unrestrained detail. The fears and wants of our protagonist Anne (played precisely by Anamaria Vartolomei) are palpable throughout. Nothing is held back in this film, and if you find yourself sick in parts, then it has achieved its goal of realistically conveying what it’s like to stay alive in a society that fails to recognize your needs. 

Clocking in at just under four hours, Hu Bo’s first and last feature film—before his tragic death at the age of 29—is a sprawling indictment of a country that the filmmaker must have viewed as positively hostile and suffocating. Following several characters whose paths intersect as they try to escape their current circumstances, An Elephant Sitting Still creates a truly oppressive atmosphere that may not lead you to the answers you expect, but it should leave you feeling haunted for a long, long time. Beautifully scored, shot, and acted, Hu’s film offers practically no hope but it keeps on moving with a sense of freedom and determination all its own. This is as honest a film can get; Hu has left behind a moving legacy.

Based on the Austrian novel, The Piano Teacher is as brilliant and as disturbed as its protagonist. The film follows Erika Kohut (Isabelle Huppert), the repressed masochist in question, and the trainwreck of a relationship that she develops with her student Walter Klemmer (Benoît Magimel). Their dynamic is undeniably toxic. Austrian auteur Michael Haneke frames each scene with clinical detachment, but it is absolutely brutal how the two characters try to assert control over each other, engage in sadomasochism, and repeatedly violate each other’s boundaries. Huppert’s heartrending performance fully commits to the merciless treatment Erika receives. But more tragic is the way Erika’s unusual relationship could’ve freed her, could’ve helped her process her abuse, and instead, reinforces her repression. It’s scary to make yourself vulnerable by admitting your desires, only for them to be used against you.

You’ve probably watched and heard about enough Holocaust films to expect a formula, but you might want to put all that aside going into The Boy in Striped Pajamas. Bruno, the son of a WWII Nazi commandant forms an unlikely friendship with a Jewish kid his age in his father’s concentration camp. The film is World War II told through Bruno’s eyes, and while you might not get why this movie is so highly praised in its first scenes, the twisting and profound second half will have you recommending it to everyone in need of a moving story well executed, or quite simply a good cry.

In the first few minutes of Mass, hushed tones, solemn movements, and awkwardly averted eyes hint at an unspoken tragedy that haunts everyone in the film. The four main characters discuss it during a sit-down, but even then it remains unspeakable; such is the dedication of first-time full-length director Fran Kranz in depicting the reality of tragic events. Not much is done in the way of plot twists and shocks, but in place of those, Mass makes clever use of close-up shots and unmoving settings to portray the privacy and paralysis of grief. For this reason, Mass often feels like a masterful play brought to life, but also more than that, a brilliant portrait of healing—or at the very least, coping with the everlasting aftermath of loss. 

While the film adapts some of Shakespeare’s histories, you don’t need to know Shakespeare to appreciate My Own Private Idaho. In fact, instead of focusing on the Prince Hal character, Scott Favor (Keanu Reeves), the film centers on his narcoleptic friend Mike Waters (River Phoenix). Both of them are young street hustlers in Portland. However, unlike Favor, Waters has no reliable family, inheritance, or support system waiting for him to give up his job. Waters only has his body. Writer-director Gus Van Sant doesn’t really focus on the sex or the narcolepsy – these flash by us only as a state-of-mind experience, with time-lapses and freeze-frames to impart to us Waters’ detachment. Instead, Van Sant cares more about Waters’ seeking connection. It’s why the surreal shots speed by us so fast, and why the natural, lived-in scenes remain in our heads. It’s why Waters’ campfire confession, crackling under Phoenix’s earnest voice, feels so powerful. And it’s also why his later rejection feels so painful.

The story of the Von Erich family is excruciatingly sad, but Iron Claw doesn’t dive right into the tragedy. Instead, it takes care to paint a picture of a close-knit family that’s filled with just as much warmth, jealousy, affection, and resentment as the next bunch. Durkin masterfully draws you into their circle so that everything that happens next is sure to cut deep. The choreography, chemistry, color—everything is carefully and beautifully set up, but the casting is what stands out the most. This wouldn’t have worked as well if it weren’t for the inspired move to pair Zac Efron, Jeremy Allen White, Harris Dickinson, and Stanley Simons as brothers and partners. On the internet, people have been dubbing The Iron Claw as “Little Women and The Virgin Suicides for men” and it’s not hard to see why. Apart from the sibling bond over glory and growing pains, all these films are also powerful explorations of gender. Iron Claw is a vicious takedown of toxic masculinity, while also being a searing family drama and an incredible showcase for Efron and company.

Prophet’s Prey is a documentary on the sect known as Fundamentalist Latter-Day Saints and its leader, Warren Jeffs. Claiming to have inherited a direct connection to God, Jeffs has used this pretext to control a closed society of thousands of individuals on a shockingly personal level, as well as marry dozens of underage girls and harvest the community’s financial resources on behalf of “the church.”

The subject is deftly handled by filmmaker Amy Berg (Deliver Us From Evil). Here she presents most of the story via interviews with the people whose tenacity was instrumental in exposing  Jeffs. Woven throughout the film, too, is the haunting, disembodied voice of Jeffs himself, in recorded words to his followers, along with film footage of present-day FLDS communities. What emerges is the picture of a terrifying madman who still wields a disturbing amount of power over thousands of active congregants. Absolutely riveting.