2021 Edition: Discover the Top 15 Most Heartbreaking Movies on Amazon Prime Video – Top

The saddest movies on Prime Video are some of the saddest films to be found anywhere. This doesn’t necessarily mean they’re going to be immersed fully in bleak stories, depressing characters, and hopeless endings. Some will, but the concept of a sad movie is one that can be found in a variety of genres and types of films.

Comedy can be absolutely heartbreaking, under the right circumstances, or even ask a horror fan to list off some of the saddest moments from their favorite films. This sadness can be cathartic, but it can also just as easily leave us in a state of casual-or-worse despair. The point is that a sad movie is, up to a point, a subjective matter. It is largely in the eye of the beholder.

You can see that for yourself, as I take us through some of the saddest movies you can find on Prime Video. Drama will be represented quite well here, but the idea also is to see just how many differing ways there are to watch a movie in which sadness is either the result, or something deeply ingrained in the DNA of what we’re watching.

You probably don’t want to watch more than three of these in a row.

 

The Saddest Movies on Amazon Prime Video

1. Adaptation (2002)

Director: Spike Jonze

Writer’s block is bad enough. Life can get even more charming when it combines with the unstoppable feeling that you are also going completely insane. Barring that, you’re just stressed out, and the world around you is in fact the part that’s getting stranger.

Adaptation is still probably the least depressing movie to feature a Charlie Kaufman screenplay (Synecdoche, New York). However, that’s not really saying a lot. All of his movies carry the proud torch of being some of the bleakest films ever created.

This loosely autobiographical film, which also features the bonus insanity of Nicolas Cage playing a version of Kaufman and his (fictional) twin brother, is pretty funny sometimes. However, as it mangles the life of Kaufman with that of the author of the book he’s trying to adapt (Meryl Streep, still managing to stand out here), things get uncomfortable at best, and extraordinarily sad at worst. It works pretty well.

 

2. Big Fish (2003)

Director: Tim Burton

As far as I’m personally concerned, aging goth kid Tim Burton hasn’t made a film as strikingly original and multifaceted as 2003’s Big Fish. A story of family with a decided lean into whimsy and fantasy, the movie is not in any particular depressing mode. This is not inherently a sad story.

Yet the movie certainly has the power to evoke something very powerful, and perhaps, as we separate fact from fiction in the life of Edward Bloom (brilliantly played by both Ewan McGregor and Albert Finney), something deeply personal. Of course, this kind of thing is always bittersweet. Hence the movie’s place here.

Big Fish is a wealth of memorable characters, and a story that brings to mind our own stories.

 

3. The Fisher King (1991)

Director: Terry Gilliam

The Fisher King has great warmth and humanity to it. These qualities are almost always present in the films of Terry Gilliam, but they are also sometimes obscured by chaos and general weirdness. That’s fine, but knowing this makes The Fisher King all the more impressive. It might be the most optimistic movie in Gilliam’s filmography.

But it certainly makes you work for that optimism. An alcoholic talk radio host (Jeff Bridges), in the depths of a sorrow brought about by his own callousness, finds a potential savior in a homeless man (Robin Williams, in what might be my favorite performance of his) whose life was touched in a horrible way by the actions of Bridges’ character.

Without question, this story of profound light and hope carries with it some pretty brutal darkness.

 

4. Hard Eight (1996)

Director: Paul Thomas Anderson

Losers are legion in the films of Paul Thomas Anderson. The old gambler taking on a young protégé under the relentless atmosphere of neon, opportunity, and regret in Las Vegas. This is the main thread of Hard Eight, but the film is also an odyssey of people who are on the fringes for one reason or another. The most successful people in this film, and indeed, in many Paul Thomas Anderson movies, are still losers, but with the added shade of being shaped by cruelty.

Hard Eight has an incredible, engaging energy running through it. You can appreciate that, as well as the powerful performances by Phillip Baker Hall (shame on the Academy for completely overlooking this) and John C. Reilly.

At the same time, there is no getting around the fact that this movie, which also features Phillip Seymour Hoffman and a decidedly-less-annoying-than-usual Gwyneth Paltrow, is as depressing as it is thrilling.

 

5. Husbands (1970)

Director: John Cassavetes

The justifiably celebrated works of indie film iconoclast John Cassavetes have moments of tremendous joy, anger, and perhaps, above all others, fear. His characters are often driven by utter terror at one thing or another.

More often than not, the fear of one thing (a bad business deal, the mental anguish of a spouse) is an underlying cause for something deeper. That is not the case with Husbands, which depicts three men essentially going all-in on a slow-burn nervous breakdown, when one of their friends passes away rather suddenly.

Sure, three dudes having a convoluted midlife crisis may not sound very interesting, but I can assure you that Husbands goes deeper than that. It also refuses to romanticize these men, played to perfection by Ben Gazzara, Peter Falk, and Cassavetes. We watch them fail miserably at almost everything they do. That is funny, up to a point, but watching such desperate raging against the dying of the light, smacked back towards them with barely a flicker of recognition from the universe, is dark stuff indeed.

 

6. The Lady in the Van (2015)

Director: Nicholas Hytner

Don’t get too hung up on the “mostly true” claim attached here. While indeed based in a strong measure of reality, the factualness of The Lady in the Van isn’t really important. What matters more, throughout our time with a woman who lived in a van in someone’s driveway for 15 years, is how deep into the grim reality of this story can get.

The humorous moments are certainly prominent throughout. However, with someone as versatile as Maggie Smith, and with her mere presence being enough to establish something believable, the movie’s somber moments can be devastating.

While the overall tone of The Lady in the Van, which also benefits from Alex Jennings and Jim Broadbent in the cast, is not a sad one, the movie will nonetheless leave you feeling the agony of hoping it all works out in the end.

 

7. The Last Black Man in San Francisco (2019)

Director: Joe Talbot

The very-real specter of gentrification makes the plot of The Last Black Man in San Francisco not only a pretty depressing one, but also a harrowing journey for its two protagonists. This is a frantic, inventive movie. If we were ranking the saddest movies on Prime Video, it would be somewhere near the top.

As Jimmie (Jimmie Falls) and Mont (Jonathan Majors, who particularly stands out for his performance here) unravel the history of a beautiful home with a link to Jimmie’s personal history, The Last Black Man in San Francisco hits a stride of poignant satire, character development, and a thousand little unhappy details of a world that seems at least annoyed they are around in the first place.

The Last Black Man in San Francisco is sad as hell, and also proof that originality in filmmaking is not quite as dead as some claim. If you haven’t seen this, make it a point to change that.

 

8. Only Lovers Left Alive (2013)

Director: Jim Jarmusch

Quietly hilarious and deeply depressing. Only Lovers Left Alive, a film very much in the vein of the languid, contemplative films in Jim Jarmusch’s library, manages to exist with both of those qualities from start to finish. At no point do I feel like the humor inherent in this story of two vampires who reconcile and try to make the best of the wretched 21st century overwhelms the many, many bleak elements that dominate their lives and our viewing experience.

It’s also a blast to just see actors like Tilda Swinton, Tom Hiddleston, John Hurt, and the gone-entirely-too-young Anton Yelchin in a film with dry humor and spiritual horror. You just won’t lose sight of the fact that the world is falling apart. Setting your story largely in Detroit is a good way to tell the audience exactly what they’re in for.

What you’re in for is a very odd, but very satisfying vampire story.

 

9. Reservation Road (2007)

Director: Terry George

Two very different families are brought together by an unfathomable tragedy. This movie gets sorrowful right up front, and it doesn’t really let up, as these characters and their various relationships deepen, surprising us at a relentless, almost draining pace.

Reservation Road has a cast packed with people who know how to be memorable in something like a high-concept crime drama. Actors like Joaquin Phoenix, Mark Ruffalo, Jennifer Connelly, and Mira Sorvino all have resumes consisting of characters who are made to go through absolute and unflinching hell on earth.

Their best characters hit our emotional intelligence in a way that leaves those feelings stripped down to something we sometimes don’t want to actually address. Reservation Road is an exceptional example of that. When someone we love dies, nothing is ever really the same. Reservation Road will force you to think about that.

 

10. River’s Edge (1986)

Director: Tim Hunter

A group of teenagers are thrust into something that shatters and then sadistically reshapes their lives in one of the most depressing dramas made in the 1980s. It gave Crispin Glover, Keanu Reeves, and Ione Skye Leitch early, memorable roles in one of the most enduringly popular films made in this era.

River’s Edge, which forces its complex characters to deal with a murder committed by one of their own, against one of their own, was also part of the considerable comeback Dennis Hopper made in the 80s. His unbalanced Feck is just one of the many dark threads running through a story that is as stunning in its writing and style as it is absolutely gut-punching.

Those punches never stop, but the movie doesn’t destroy you by the end. I suspect it will stay with you in a very striking way, but these characters are not punished. As bad as it gets for them, I will at least tell you that their humanity still finds a way to come through.

 

11. Sunset Boulevard (1950)

Director: Billy Wilder

“I am big. It’s the pictures that got small.”

With that line, Gloria Swanson gave us the entire sorrowful history of silent film legend Norma Desmond.

That isn’t to say the rest of the movie isn’t a fascinating character study, combined with sharp satire on Hollywood itself (some of which can still find relevance today), as we watch an ambitious, desperate screenwriter (William Holden) try to manipulate Desmond into a comeback with coattails spacious enough to accommodate him. However, the single line summarizes the character, the plot, and what we can ultimately expect in this stylized, energetic, but very sad story.

Even if the movie didn’t have that infamous opening (you’ll see), Sunset Boulevard makes it clear pretty much at the start that no one is going to experience a happy ending.

At least, and this is particularly true in the tragic end of Norma, as far as the actual waking world is concerned.

 

12. Trees Lounge (1996)

Director: Steve Buscemi

Besides being one of our best living actors, Steve Buscemi is also an accomplished film and television director. Trees Lounge remains his best and most intimate work to date, offering a glimpse into the lives of some of the most reliable losers and dirtbags you’ve met in quite some time.

Shades of Charles Bukowski and the dissatisfied, consistent alcoholic can be found throughout this film, which Buscemi also wrote and stars in. The characters here aren’t going anywhere. They are not going to be redeemed. They are not going to make good decisions. This movie can sometimes feel like either version of Shameless. Except there isn’t a dark sense of humor to break up the wretchedness.

No, I don’t think Trees Lounge is prohibitively depressing. I would still ask you to keep in mind that this movie is exactly what any trailer or synopsis suggests it will be.

 

13. Unbreakable (2000)

Director: M. Night Shyamalan

Unbreakable might just be the gentlest and saddest superhero movie of all time. That doesn’t work for everyone, especially through the filter of someone as specific and distinctive as M. Night Shyamalan, but it does establish the film as a truly unique piece of this genre. It proved then, and reminds us now, that superhero stories can be told in any number of ways.

Unbreakable gets on this list of the saddest Prime Video movies just for the ending alone. Truly, one of the most heartbreaking of anything you will find on this list.

At the same time, Bruce Willis as an (mostly) invincible man, whose super strength is supplemented by the ability to see the crimes committed by those he touches, consistently weighs the movie down with the agony of indecision, of refusing to come to terms. The film also has some pretty unhappy thoughts to share about the notion of destiny. This is really driven home in the portrayal of Mr. Glass by Samuel L. Jackson.

To date, I would still call Unbreakable his best work as an actor.

 

14. We Need to Talk About Kevin (2011)

Director: Lynne Ramsay

I’m sure having actual experience enhances watching We Need to Talk About Kevin, one of the darkest films ever made about motherhood, but I don’t think it’s a requirement. You’re almost certainly going to agree that this film is horrific in the types of sadness, often spiraling into rage, it presents. You’re also probably going to concede that this is also one of the most disturbing films ever made.

With Tilda Swinton as a woman who gives up everything for a decision that ultimately and understandably does not satisfy her, and Ezra Miller as her increasingly disturbed son (John C. Reilly is also stellar as Kevin’s father), this film hits on the emotional and psychological levels. It is very difficult indeed to watch this relationship between mother and son unfold into something hideous.

It’s also just as difficult to consider the implications of what these characters, particularly Tilda Swinton as Eva, are experiencing. We Needs to Talk About Kevin is first and foremost supremely uncomfortable in what it discusses and suggests.

However, if you simply want to take this film as pure horror, I suppose that’s fine, too.

 

15. The Wrestler (2008)

Director: Darren Aronofsky

Mickey Rourke’s own post-fame life on what some might call skid row is worth touching on. It does indeed provide the story of faded pro wrestling hero Randy “The Ram” Robinson in The Wrestler with something special and entirely unique to this film.

At the same time, as we watch Randy struggle with health, a disintegrated career, the possibility of love (Marisa Tomei is in rare form as Cassidy, a stripper Randy hangs out with), and the need to reconnect with his daughter (Evan Rachel Wood, who brings a great deal to her scenes with Rourke), we are fully immersed in a great, deeply saddening cinematic story.

The fact that Randy is in the place he is at in life is sobering enough on its own. What makes The Wrestler a devastating film, as exciting as it can sometimes be, is how deeply and permanently we watch Randy put the final nails in the coffin of a life that could only sustain but so many bad decisions.

The last decision he makes in the movie, at any rate, is his own. There is a haunting peace to this movie.

Thankfully, Mickey Rourke’s own story is a lot happier.

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