The 50 Saddest Movies to Watch on Amazon Prime

Understated in budget but lavished with praise, this semi-autobiographical drama by Daniel Destin Cretton flings its audience into the chaotic lives and personal crises of at-risk youths and the passionate social workers that aid them. In his first feature film, the young director draws the viewers into the storm of events and the emotional ups-and-downs of social work in America, going from uplifting to depressing and back – and every emotion in-between.

Set in the real-life and eponymous group home Short Term 12, devoted but troubled foster-care worker Grace is played by Brie Larson, whose shining performance in her first leading role was lauded by critics. Fans will also recognize the supporting actors Lakeith Stanfield and Rami Malek, who broke out in this movie. Short Term 12 is now considered one of the most important movies of 2013 – some say of the decade – owing to its immaculate writing, intimate camerawork, and gripping performances.

Aptly named ‘Rupert Grint on speed’ by one critic, Antoine-Olivier Pilon plays Steve, an abusive ADHD adolescent who just got out of a juvenile care facility for setting fire to the school cafeteria and injuring a fellow student. Similarly, his mother Diane, played by Anne Dorval, is a type of Lorelai Gilmore on speed – and to say that sparks fly when they clash is an understatement. But help comes from unexpected places: ‘Die’ makes friends with Kyla, an anxious teacher living across the street, who then gets sucked into this crazy, volcanic mess.

Mommy is the fifth feature film by French-Canadian don’t-call-him-a-hipster director Xavier Dolan and won the Cannes Jury Prize for its originality. It is shot in the 1:1 ‘portrait’ format, but every now and then a moment of exhilaration will crack open the frame. The brutality on screen is sugar-coated by an all-over-the-place soundtrack that includes the Counting Crows, Celine Dion, and Blue (Da Ba Dee) by Eiffel 65.

Shrill, violent, and demented, this out-of-control dark comedy will punch you in the guts. But it also aims straight for the heart and doesn’t miss. Prepare to be continually torn between laughing out loud, clawing your seat, and covering your mouth in shock.

Legend has it that director Derek Cianfrance had the co-stars and co-executive producers Michelle Williams and Ryan Gosling live together in the same house for a month in preparation of their roles. The fictional couple they play in Blue Valentine lived in the same house. True or not, this created the harsh proximity, intensity, and claustrophobia that is a hallmark of this production. Blue Valentine brings us painfully close to the couple’s attraction as well as their agony.

In this way, Blue Valentine is a heart-breaking examination of the decaying shell of a once-bright marriage. As sad as it is sexy, it mixes intense flashbacks of past desire with the grim reality of married life’s monotony. It boasts an electrifying performance from Michelle Williams and Ryan Gosling, who seamlessly combine tenderness and lust, rage and sadness. This is a guaranteed tear-jerker, so make sure you’ve brought your Kleenexes!

Revealing the gaps in the social safety net, I, Daniel Blake, is a tale centered around a blue collar worker navigating the welfare system in England. At a time where class and social mobility could not be more politically salient, this film calls into question the notion of the “citizen” and exposes the inaccessibility to the social protections in which one presumes entitlement.

At the forefront of this, is a heart-warming parable of paternal companionship between Daniel (played by Dave Johns) and a single mother – Katie – (played by Hayley Squires) who is wading through similar terrain. The acting in the film is unfathomably raw which cultivates the deepest source of gut wrenching compassion. Ken Loach has created a film that exposes the true power of empathy, leaving you feeling helplessly human.

A very poetic film by Tony Kaye (American History X) about an English Literature teacher (Adrien Brody – “The Pianist”) who only works as a substitute in schools which are located in very poor urban areas. The reason behind his choice is that he doesn’t want to bond too much with his students and colleagues because he is trying to control his dark emotions about life and the triviality of our existences (although it sounds depressing it is absolutely not). He also takes care of his last family connection, his grandfather, to whom he is very close and who lives in an elderly home. Unsurprisingly, their relationship is very emotional and deep. Every time you think about your existence, your place in the world, your interactions with other people; watch Detachment.

Joshua Oppenheimer’s daring feat is a documentary unlike anything ever done. Despite it being one of the most difficult things to watch for any human being (or because of it), The Act of Killing received praise across the board, including an Academy Award nomination. Without Oppenheimer’s efforts, you might have never heard of the unspeakable events that happened when, in 1965-66, Suharto overthrew the then-president of Indonesia and a gangster-led death squad killed almost a million people. Did they pay for their crimes? Quite the contrary: said gangsters went on becoming political mainstays in modern-day Indonesia, are still now heralded as heroes, and admit to all these crimes with a smile and not a hint of regret. The gruesome twist of this documentary is that Oppenheimer asks them to re-enact the killings in surreal, sadistic snuff movies inspired by the murderer’s favorite action movies. You are forced to stand idly by as they re-create brutal mass murder and joke about raping a 14-year-old. However, somewhere amidst this terrifying farce, the killers, too, have fleeting moments of realization that what they’re doing is wrong. If you make it through this in one piece, try watching its more victim-focused follow-up The Look of Silence. Bone-chilling but very powerful stuff.

There are movies that leave you matured after you finished watching. You mature because you are forced to walk in someone’s shoes and confront yourself with issues that you are not affected by. The Sea Inside is one of those movies –⁠ and won an Academy Award and a Golden Globe for it. Directed by Alejandro Amenábar, who you might know as the director of The Others, it tells the true story of Ramón Sampedro’s decade-long fight for the right to end his own life. After he became quadriplegic after a diving accident, he was confined to the same bed in the same room for 26 years, except when he visited the hospital. Not an easy subject to say the least but Amenábar helps the fascinating story along with stylish directing, while Javier Bardem delivers a stellar performance to go with it. Thanks also to Ramón Sampedro’s sunny real-life nature, this heart-wrenching watch also has plenty of uplifting moments.

In Aftersun, Sophie recalls a holiday she took as an eleven-year-old in the ‘90s with her father. Video recordings help jog her memory, but she’s looking for more than just a blast from the past. Rather, she seems to be seeking answers to fill in the gaps between who she knew as her father and who he really was: an immensely nice but deeply troubled man.

At first, Aftersun looks like a simple but beautiful story about father and daughter bonding over the course of a summer trip. But within minutes, it’s clear that there are layers to Aftersun, emotionally and editorially, that aren’t always explained but nonetheless enrich the movie with profound meaning. Stirring, complex, and surprisingly inventive, it’s not surprising that Aftersun is one of the most beloved films of the past year. 

It has become increasingly rare to find films made in Afghanistan, so when a movie like Osama comes along, it becomes nothing short of essential viewing. This is a profoundly depressing but beautifully crafted story of a young girl made to look like a boy so as to go unnoticed by Taliban forces while trying to help her family. It’s a simple film wherein this character’s budding awareness of her girlhood is set against a terrifying backdrop of violence, abuse, and fundamentalist extremism—all of which director Siddiq Barmak keeps off the screen.

Barmak knows exactly what to point his camera at, covering multiple angles of life in Taliban-controlled Afghanistan without calling attention to himself, and still finding ways to show the smallest shreds of sympathy and support hiding within this society. And in the lead role, a teenage Marina Golbahari delivers a towering, heartbreaking performance that never registers as anything but authentic. The fear that she embodies is almost too real to watch without becoming afraid yourself. Osama is incredibly difficult viewing, but it’s a truly valuable work of art that deserves to be preserved.

Nebraska is a poem distilled into a film. Peter Travers from Rolling Stone says “is it a comedy or a drama? Both at the same time, as life itself.” Everything about it is perfect: the acting, the photography, the story. In case that’s not enough and you need to know the plot to get convinced, I’ll tell you that it’s a road movie about a senile old man and his son. If you still want more information, you can Google it, but come on! You’ll just be wasting time that would be better spent on watching this masterpiece.