The 50 Saddest Movies to Watch on Amazon Prime

The 50 Saddest Movies to Watch on Amazon Prime

June 13, 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.

1. Short Term 12 (2013)

best

9.9

Country

United States of America

Director

Destin Cretton, Destin Daniel Cretton

Actors

Alex Calloway, Angelina Assereto, Brie Larson, Diana Maria Riva

Moods

Challenging, Depressing, Inspiring

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.

2. Mommy (2014)

best

9.7

Country

Canada

Director

Xavier Dolan

Actors

Alexandre Goyette, Anne Dorval, Antoine-Olivier Pilon, Catherine Brunet

Moods

Challenging, Depressing, Discussion-sparking

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.

3. Blue Valentine (2010)

best

9.5

Country

United States of America

Director

Derek Cianfrance

Actors

Alan Malkin, Ashley Gurnari, Barbara Troy, Ben Shenkman

Moods

A-list actors, Challenging, Depressing

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!

4. Love and Mercy (2014)

best

9.5

Country

United States of America

Director

Bill Pohlad

Actors

Bill Camp, Brett Davern, Brian Wilson, Carolyn Stotesbery

Moods

Depressing, Emotional, Sunday

If you’re a fan of the Beach Boys’ legacy, or you want to find out more about Wilson, the person, this movie will give you what you need. It has been widely praised as being true to the facts – even by Bryan Wilson himself. But thanks, in part, to the incredible writing by Oscar-nominated Oren Moverman and the work of director Bill Pohlad, this is much more than a fact-based fictionalization of a famous musician’s biography. It is a singularly convincing account of the artistic process and the effects of mental illness.

Love and Mercy tells the tale of two Bryan Wilsons: the first of a young and slightly square-looking musical pioneer in the 1960s, when Wilson was working on Pet Sounds, the Beach Boys’ most ambitious and ground-breaking album. Paul Dano’s performance here is nothing short of perfect. And, second, the tale of the tormented, middle-aged Bryan Wilson, played by John Cusack, during a time when he was under treatment for his deteriorating mental health in the late 1980s. The juxtaposition of these two very different people and the brilliant performances of Cusack and Dano will completely absorb you and change the way you look at things. A unique and beautiful film!

5. I, Daniel Blake (2016)

best

9.5

Country

Belgium, France, UK

Director

Ken Loach

Actors

Briana Shann, Dan Li, Dave Johns, Dave Turner

Moods

Character-driven, Depressing, Emotional

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.

6. Farewell My Concubine (1993)

best

9.2

Country

China, Hong Kong

Director

Chen Kaige

Actors

Dan Li, David Wu, Fei Zhenxiang, Ge You

Moods

Challenging, Character-driven, Depressing

Thirty years after its release, the first ever Chinese language Palme d’Or winner has finally been made more accessible through Criterion Channel through its uncut 4K restoration. Farewell My Concubine is one of those classical epics that is considered essential viewing, but even with its near 3 hour runtime, the film still holds up all these decades later with its startlingly heartrending love story and depiction of the tumultuous shifts of 20th century China. Director Chen Kaige masterfully balances both sides, tapping into the pain Dieyi (Leslie Chung) chooses as he clings to the classical opera, the very art form that allows him a sliver of his unrequited love to be realized, but that is also limited depending on whichever government is in charge at the moment. It’s possibly one of the most beautiful and most miserable films ever made.

7. The Farewell (2019)

best

9.1

Country

China, United States of America, USA China

Director

Female director, Lulu Wang

Actors

Aoi Mizuhara, Awkwafina, Chen Han, Diana Lin

Moods

Depressing, Emotional, Inspiring

Many things clash in this beautifully layered, semi-autobiographical film of American director Lulu Wang: cultures, morals, and emotions. The result is a type of comedy that is complex and bittersweet⁠—and based on a true lie: this is the story of a Chinese grandma whose family won’t tell her that she is fatally ill. Instead, they organize a fake wedding in China, where everyone gets together to bid a farewell to the unwitting matriarch (played by Zhao Shuzhen). The fake wedding is, in fact, a premature funeral for a person unaware that she is going to die. Played by rapper and comedian Awkwafina, Billi, a New-York-based Chinese-American with a complicated relationship to China, embodies the cultural and moral question at the heart of this story: is it right or wrong not tell grandma? It is thanks to Wang’s deft writing and Awkwafina’s outstanding performance that The Farewell homes in on answers without ever being melodramatic. Warm, honest, and beautiful.

8. Detachment (2012)

best

9.0

Country

United States of America

Director

Tony Kaye

Actors

Adrien Brody, Betty Kaye, Blythe Danner, Bryan Cranston

Moods

Challenging, Dark, Depressing

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.

9. The Act of Killing (2012)

9.0

Country

Denmark, Finland, Germany

Director

Christine Cynn, Female director

Actors

Adi Zulkadry, Anwar Congo, Haji Anif, Herman Koto

Moods

Dark, Depressing, Discussion-sparking

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.

10. The Sea Inside (2004)

best

9.0

Country

France, Italy, Spain

Director

Alejandro Amenábar

Actors

Adolfo Obregón, Alberto Amarilla, Alberto Jiménez, Alberto Jiménez

Moods

Dark, Depressing, Discussion-sparking

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.

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