The 50 Saddest Movies to Watch on Amazon Prime

The 50 Saddest Movies to Watch on Amazon Prime

February 28, 2024

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With so many viewing options at our fingertips, why do we still seek out films that depress us? As counterproductive as they may seem, sad movies—when handled well—still offer a necessary release that can’t be found in hours of feel-good content. So while you may have to be in a particular mood to sit through and really process many of the films on this list we’ve put together, profound lessons still await the patient, attentive viewer. As one of the biggest streaming services in the world, Amazon Prime arguably has the widest variety of movies to offer to a mass online audience, which makes it a great place to experience every shade of depressing, cathartic, invigorating sadness.

21. The Piano Teacher (2001)

best

8.6

Country

Austria, France, Germany

Director

Michael Haneke

Actors

Anna Sigalevitch, Annie Girardot, Benoit Magimel, Cornelia Köndgen

Moods

Challenging, Dark, Depressing

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.

22. The Boy in the Striped Pajamas (2008)

best

8.5

Country

UK, United Kingdom, United States of America

Director

Mark Herman

Actors

Amber Beattie, Asa Butterfield, Béla Fesztbaum, Cara Horgan

Moods

Depressing, Dramatic, Emotional

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.

23. Mass (2021)

best

8.5

Country

United States of America

Director

Fran Kranz

Actors

Ann Dowd, Breeda Wool, Jason Isaacs, Martha Plimpton

Moods

Challenging, Character-driven, Depressing

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. 

24. To Leslie (2022)

best

8.5

Country

United States of America

Director

Michael Morris

Actors

Alan Trong, Alan Wells, Allison Janney, Andre Royo

Moods

Challenging, Character-driven, Dark

To Leslie follows the eponymous Leslie (Andrea Riseborough), a Southern woman who finds herself at the bottom of the barrel after finally using up every penny of her $190k lottery win. Out of work, friends, and family, she drowns herself in alcohol—that is until a kind soul in the form of motel owner Sweeney (Marc Maron) takes her in and gives her a shot.

To Leslie starts off a bit slow, and its premise may seem like it’ll give way to weepiness, but it’s worth sticking by till the end. The film only gets better, especially with the arrival of Maron, whose presence lends the film a much-needed buoyancy. It’s also worth noting that unlike many of its kind, To Leslie avoids the poverty porn trap by depicting issues like addiction and indigence with nuance, honesty, and humanity.

25. My Own Private Idaho (1991)

best

8.5

Country

United States of America

Director

Gus Van Sant

Actors

Chiara Caselli, Flea, Grace Zabriskie, Gus Van Sant

Moods

Depressing, Emotional, Thought-provoking

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.

26. Threads (1984)

best

8.5

Country

Australia, United Kingdom

Director

Mick Jackson

Actors

Ashley Barker, Brian Grellis, David Brierly, Dean Williamson

Moods

Challenging, Dark, Depressing

Named for all the connections that form a functioning society, Threads is a harrowing look at what might happen when those ties are rent apart by nuclear war. This British TV movie — released during the Cold War — so violently seized on the nuclear anxieties of the time that its premiere was dubbed “the night the country didn’t sleep.” Depressingly, it hasn’t lost that initial resonance, and so it remains a panic attack-inducing watch.

Threads begins in the kitchen-sink vein of a Ken Loach movie. In the northern industrial town of Sheffield, a young couple from different social classes (Reece Dinsdale and Karen Meagher) discover they’re about to be parents — but looming above their small-scale drama are the clouds of war, as televisions and radios blare out the details of escalating tensions between the US and the USSR. And then, it happens: the town is strategically bombed, and Threads unfurls into an unrelenting nightmare. In the documentary-like approach that follows, it spares no graphic or emotional detail, charting both the personal devastation caused by the bomb and the annihilating impact of the nuclear holocaust on all the vital infrastructure we take for granted. In short, one of the bleakest, most terrifying movies ever made.

27. The Iron Claw (2023)

best

8.5

Country

United Kingdom, United States of America

Director

Sean Durkin

Actors

Aaron Dean Eisenberg, Cazzey Louis Cereghino, Chad Governale, Chavo Guerrero Jr.

Moods

Action-packed, Dark, Depressing

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.

28. Prophet’s Prey (2015)

best

8.4

Country

United States, United States of America

Director

Amy J. Berg, Female director

Actors

Nick Cave

Moods

Dark, Depressing, Discussion-sparking

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.

29. Clean, Shaven (1993)

best

8.4

Country

United States of America

Director

Lodge Kerrigan

Actors

Eliot Rockett, Ismael Ramirez, J. Dixon Byrne, Jennifer MacDonald

Moods

Challenging, Depressing, Raw

How do you get rid of an irremovable stain? In Lodge Kerrigan’s psychological thriller, characters shave the dirt off in hopes of returning things to their original pristine state. In the process of doing so, however, permanent damage is incurred, which begs the question: is the eradication of filth correspond to cleansing?

Through erratic editing and an unsettling sound design, not only does Clean, Shaven put its audience in the disturbed mind of the protagonist Peter Winter, it also effectively depicts his struggle (and inability) to retain sanity amidst a prejudiced society. The film contrasts post-Cold War paranoia with the nobility of paternal love, and finds tragedy in Peter’s futile attempts to prove his “cleanliness” in a world intent to brand him as dirty.

30. Dead Man Walking (1996)

best

8.4

Country

United Kingdom, United States of America

Director

Tim Robbins

Actors

Adam Nelson, Adele Robbins, Anthony Michael Frederick, Arthur Bridgers

Moods

A-list actors, Depressing, Discussion-sparking

Told with grace and maturity without sensationalizing its subject matter, Dead Man Walking expertly walks the line between taking a moral stand and keeping the messy humanity of its characters intact. Though it may seem just like a legal drama or prison film on the surface, writer/director Tim Robbins weaves in commentary on class and the role religion is expected to play in middle class Southern communities—especially in the context of justice and crime. Sean Penn and Susan Sarandon (in the role that won her her Oscar) play every side to this drama with remarkable control, building an unlikely rapport that culminates in a finale that’s as moving as any great tear-jerker. It may be tough to watch at times, given the raw emotions that are laid bare, but Dead Man Walking remains relevant even today.

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