The 50 Saddest Movies to Watch on Amazon Prime

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.

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.

Putting the inherent eeriness of stop motion animation to perfect use, Charlie Kaufman and Duke Johnson’s Anomalisa create a legitimately disturbing experience of a man’s paranoid delusions, as he tries desperately to make a real human connection while perceiving everyone around him as the same person. It’s that (unfortunately) rare animated film that understands that this medium can tell complex, even terrifying, stories for grown-ups while respecting their intelligence. And it’s still gorgeously put together, with seamless movements from the character puppets and evocative lighting and cinematography that puts the film firmly in the uncanny valley. It’s a tougher watch than it looks, but the depth of feeling it captures is nothing short of totally human.

Andrew Garfield is a single father living with his own single mother in their family home. In the aftermath of the financial crisis, they find themselves evicted from their home by a businessman – Michael Shannon in a role as intriguing as Gordon Gekko in Wall Street, if not more. Desperate for work, Garfield’s character starts working for the same businessman, ultimately evicting other people. A star-packed, gritty and sobering tale on capitalism and our the lengths to which we’re ready to go to save face – while at the same time risking our most important relationships.

Known for his horror films, Kiyoshi Kurosawa shifts gears and presents a family drama in Tokyo Sonata. In the film, father Ryuhei, who’s expected to be the breadwinner, loses his prestigious job and chooses to hide his firing from his family. While this premise isn’t overtly scary, the film understands the terror of being unable to maintain the current comforts of your family. And the consequences: lose your status (at best) or your life (at worst). Teruyuki Kagawa’s performance crystallizes that sense of losing control, as each expression on his face betrays how secretly afraid Ryuhei feels. The disasters that this family faces threaten to never stop, and Kurosawa executes them perfectly through excellent story structure and performance.

As time goes by, the youth doesn’t recognize how connected they are to previous tragedies, more so when it comes to war. Some even say that they have no part in it. Nobuhiko Obayashi’s later years have been preoccupied in countering this idea. Casting Blossoms to the Sky is the first of Obayashi’s anti-war trilogy, with the film inviting its audience to follow a journalist rediscovering the city of Nagaoka after the 2011 Tohoku earthquake. There’s a certain dreamlike approach to the way the various war stories are weaved together, with vibrant frames, simple CGI, and prominent green screen that grants some distance between the audience and the actual wartime reality, but it’s no less potent as Reiko interviews those that remember the scars of the past, and the rituals, practices, and art they’ve taken up in response. Casting Blossoms is a depressing story about war and disaster, one that is a tough one to watch. But it never forgets the humanity, the kindness and love that allowed Japan to recover, the very qualities we must protect and remember in ourselves.

Five orphaned sisters are put under house arrest by their uncle and grandmother after they are seen horsing around with local boys from school. While their actions were purely innocent, their behavior is viewed as scandalous and shameful by the conservative elders in their small Turkish village. After this incident, their grandmother turns her attention towards marrying off her granddaughters. Each of the five sisters rebel in their own way, but it is the youngest and rowdiest sister, Lale, who is the central protagonist of the film. She watches helplessly as each of her older sisters is married off with an increasing sense of dread and desperation. While this may sound hopelessly depressing, the movie is equal parts beautiful and tragic and floats across the screen in a dreamlike manner. Not all of the sisters escape their oppressive surroundings or their assigned fate, but the message is clear: it’s crucial to try.

This is the type of movie I completely fell in love with but cannot articulate exactly why. Maybe it’s the mixture of beauty and pain portrayed, maybe it’s the intricate sounds and beautiful imagery, maybe it’s the story, maybe it’s all of the above. A woman is hit with sudden disability after an accident and calls on an unlikely companion, a night club bouncer by the name of Ali. Together they explore her new predicament and its implications, while forming a special bond. This is a movie that will call upon your internal strength, while portraying how us humans can become strong together. Most of all it provides an immensely powerful, ultimately simple story that is both touching and will stay with you for a very long time. Directed by Jacques Audiard (A Prophet).

A powerful but quiet movie directed by Paul Dano and based on a novel of the same name by Richard Ford. It stars Carey Mulligan and Jake Gyllenhaal as a couple who move to a new town with their only child during the 1960s. Their relationship transforms after Gyllenhaal’s character loses his job as a butler and chooses to leave for a more dangerous profession, firefighting. This movie is about his wife’s response to this event and the implications of both parents’ behavior on their kid. There are no twists or turns, exciting action or plot; but Wildlife doesn’t need any of that. This moving story about a decaying family unit is portrayed in the sadness that comes with such events. The only joy comes from watching the outstanding (but expected) performances of the cast.

While being known for co-writing the Dogme 95 manifesto, Lars von Trier’s first film after breaks his rules with built sets and music added in post. Still, Breaking the Waves has plenty of von Trier’s thematic preoccupations, challenging the notions between faithfulness and sexuality by positing a married couple who cannot indulge in marital pleasure, due to being paralyzed. While the premise leads to explicit scenes, it’s more harrowing than sexy, really. It’s terribly heartbreaking as Bess does all she can for her marriage, first by praying for her husband’s return, and then following his perverse wish, partly from guilt, but partly from pleasure, even when it goes contrary to her repressive church and community. Breaking the Waves may not be an easy watch, but regardless of what you personally feel about the morality of Bess’ actions, von Trier will nevertheless bring you to empathy.