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Movies That Were Too Sad To Finish

Not all sad movies are created equal. Some might make you shed a few tears, while others might make you depressed for a couple of days. But some films are so upsetting that you can't even make it all the way to the end. These are the movies that give us characters we love, only to kill them off in dramatic fashion. These are films absolutely soaked in sorrow from the very first frame. They're set in prisons, disaster-struck cities, and cold dystopian worlds where all hope has been utterly lost. Some are little-seen indie hits, others are Oscar-winning epics, but regardless of the budget, they'll have you pressing stop on the remote and finding something far happier to do — like visiting a cemetery or listening to a playlist full of depressing songs. From death row dramas to heartbreaking biopics, these are all movies that were just too sad to finish.

A death row drama that will leave you devastated

A year after The Shawshank Redemption, Tim Robbins put on his director's hat and returned to prison with Dead Man Walking — only this 1995 drama didn't fill audiences with hope and happiness. Instead, the people who made it to the end walked away feeling absolutely wrecked.

The plot follows a Louisiana nun, Sister Helen Prejean (Susan Sarandon), who gets a letter from a prisoner named Matthew Poncelet (Sean Penn). He's been convicted of raping and murdering a young couple, and he wants Sister Helen to help with his appeal. A compassionate soul, Sister Helen decides to assist the inmate and save his soul by admitting his guilt and taking responsibility for his crimes.

Dead Man Walking takes a fair and thoughtful look at capital punishment from every angle. When Sister Helen tells the murdered girl's family that she's counseling her killer, you can totally understand their confusion and frustration. The scene when Poncelet tells his mother goodbye — and can't even hug her — would make a prison warden weep. When Poncelet is so overwhelmed by his impending death that he literally can't stand up, well, it's just devastating.

If you get this far, chances are good you'll bail during the execution scene. As Sister Helen watches, Robbins cuts between the remorseful inmate's final moments and the horrible crimes he committed. We feel sympathy and disgust at the same time. We see a cold-blooded killer and a broken, hurting human at the same time. Dead Man Walking is a hard, hard film, and we wouldn't blame you if you have to walk away.

A movie that's titanically upsetting

Okay, we know Titanic is the second highest-grossing film of all time, which means a lot of people have watched this movie more than once... but how? Sure, watching beautiful people fall in love is a lot of fun. The sets are elaborate, the costumes are gorgeous, and the practical effects are incredible. Director James Cameron really knows how to make a crowd-pleasing blockbuster. But once that ship plows into an iceberg, this high seas adventure takes a heartbreaking turn.

Honestly, how can anybody get past the scene when Jack (Leonardo DiCaprio) makes Rose (Kate Winslet) promise to never let go? Or the moment when a sobbing Rose watches Jack's frozen body sink into the cold dark of the Atlantic? Even if you cut DiCaprio and Winslet out of the movie entirely, the movie has enough sad scenes to crack the coldest heart. A stalwart band performs a hymn to comfort the dying passengers. An elderly couple holds each other in bed as water floods their cabin. A mother gently puts her children to sleep knowing full well it's the last time she'll ever see them. Titanic gets a lot of grief for that sappy Celine Dion song, but take off those cynical glasses for just a second, and you'll be the crying king of the world.

The most depressing Stephen King story ever told

Movies based on Stephen King novels (the good movies, anyway) generally do one of two things: make you scream or make you cry. The Green Mile definitely falls in the latter category. Directed by Frank Darabont, this prison drama is one big heartache after another. Just a few minutes into the film, we've got an old man weeping, and the sobbing only get worse from there. If you're one of the brave souls who made it to the end, then you probably still break down at the mention of the word "Mouseville."

The film follows the story of Paul Edgecomb (Tom Hanks), a death row guard whose life is changed when he meets an inmate named John Coffey. Played by Michael Clarke Duncan, John has the body of the Hulk and the mind of a child. But even though he's been sentenced to death, John might be the most innocent man who's ever lived. On top of that, he's a miracle worker with power over life and death. So when it comes time to lead John down the "Green Mile," Paul has to decide whether he should do his duty or spare an innocent man who's been blessed by God.

Needless to say, a movie about an innocent man condemned to death isn't going to have a lot of laughs. Almost every moment is filled with pain, from the tragic story of how John was blamed for the death of two little girls to his soul-crushing monologue about how he's ready to die because all the ugliness in the world is too much for him to bear. And then there's the final execution, a scene so sad that you'll be cursing Stephen King through your tears... if you can make it that far.

Science fiction at its absolute saddest

Released in 2001, A.I. Artificial Intelligence started as a Stanley Kubrick project before he handed it over to his bearded buddy, Steven Spielberg. The man behind E.T. carried the film down to the finish line, giving us the heartbreaking story of a little robot who wants to be a real boy.

Haley Joel Osment stars as David, a "mecha" programmed to give unconditional love to his "mother," Monica (Frances O'Connor). Monica's real son is comatose, and she hopes David can fill that lonely hole in her heart. David is more than happy to love his mommy until the end of time, but when Monica's kid wakes up, the fairy tale gets dark. After a series of unfortunate events, Monica abandons David in the woods, forcing the little mecha to search for Pinocchio's blue fairy in the hopes she can turn him into a real boy so mommy will love him again.

The plot description alone is enough to make you depressed, and that's nothing compared to watching David desperately try to please his parents, only to hurt himself or others. And the only people who don't cry when David is left by his mom are the folks who work at the Flesh Fair. The movie is one gut punch after another, and that ending — which Kubrick envisioned, not Spielberg — is horrific, but most people probably don't realize that because they were so sad that they pressed "stop" long before.

A story in the shadow of 9/11

Set in the aftermath of 9/11, 25th Hour tells the tale of Monty Brogan (Edward Norton), a convicted drug dealer who's got one day left as a free man before he's sent to prison. Once, he was a happy guy with confidence, cash, and a woman who loved him. The future looked bright. But that Monty is about to disappear. When he gets out of prison in seven years, he'll be a completely different man.

With prison looming in the future and Ground Zero literally in the background, there's a thick layer of sadness coating this entire movie. Monty spends his last 24 hours with his friends, trying to set things right before winding up behind bars. In the movie's most famous moment — when Monty stands in front of a mirror and berates everybody and everything in New York — we realize that what he hates most of all is actually himself.

Monty isn't the only character who's struggling. His girlfriend feels abandoned. One of his buddies is fighting his own confused lust for a teenage girl. Another friend is forced to do a truly terrible deed. And then there's Monty's dad, an alcoholic who wishes he could have made things easier for his son. It culminates in a final tearjerking sequence in which Monty's old man drives him to jail, dreaming about what could've been. Monty Brogan had so many opportunities, and this movie hurts so much because he ruined every one of them.

A boxing movie with an emotional uppercut

Who would've thought the guy who starred in The Good, the Bad, and the Ugly would go on to direct one of the saddest movies ever made? Million Dollar Baby tricks you into thinking it's a Rocky story, but once you drop your guard, it clocks you with a left hook of sadness.

The story follows a waitress named Maggie (Hilary Swank) who dreams of becoming a boxer. She eventually convinces a cranky old trainer, Frankie (Eastwood), to take her under his wing and show her the ropes. Maggie rises fast through the world of female fisticuffs and gets a shot at the welterweight champ. But fortune does not always smile on the bold, and after a cheap shot, she winds up paralyzed from the neck down.

There's no chance of a comeback. You can't get a rematch when the doctors take your leg. Her family tries to stab her in the back, Maggie bites her tongue off in a suicide attempt, and she eventually begs Frankie to end her pain by ending her life. There's a sadness lingering over the whole movie — from the guilt Frankie feels for his buddy (Morgan Freeman) losing an eye in a boxing match to Maggie's admission that Frankie is the only real family she's got — but the last act is pure melancholy. The ending of Million Dollar Baby is one big emotional uppercut, but you might throw in the towel long before the last round.

This wild experience will leave you wasted

Directed by Sean Penn, Into the Wild tells the true story of Christopher McCandless, a young man who donated all his money to charity, tossed away his ID cards, and set out for Alaska. McCandless was hoping to find a world where he could be connected to nature and free from materialistic wants. But when he finally set up camp in the frigid north, he quickly discovered he was in way over his head.

Played by Emile Hirsch, McCandless is a wandering nomad who encounters a collection of eccentric characters during his journeys, but more often than not, he leaves them hurting. Try to hold back the tears when his elderly friend Ron (Hal Holbrook) offers to adopt him, only to be rebuffed. Most painful of all, McCandless has abandoned his family without any word of his destination, leaving them to worry about where he might be or what's happened to him.

But really, the person McCandless hurts the most is himself. While you've got to admire his adventurous spirit, we know this trip is going to end in disaster. Through his journeys, McCandless holds to a steadfast belief that human relationships aren't worth much. Sadly, it isn't until he's starving and stranded that he realizes "happiness is only real when shared." Throughout the film, we see flash forwards to McCandless' final days, and we watch as this healthy young man becomes an emaciated wreck — dying, crying, poisoned, and alone. Into the Wild is a beautifully tragic film, but most moviegoers probably won't want to follow McCandless all the way to his doom.

Hollywood's most iconic couple breaks up

Over a decade after the Titanic set sail, Leonardo DiCaprio and Kate Winslet reunited for Revolutionary Road. But while the 1997 blockbuster was a gorgeous tale of young love, this 2008 drama spun that Titanic fantasy on its head. Perhaps it's best that Jack froze to death, because if he'd survived, maybe he and Rose would've ended up like Frank and April Wheeler.

Frank (DiCaprio) and April (Winslet) look like the perfect 1950s suburban couple. They're beautiful. Frank has a good job. April is at home raising their kids. They've got a nice house in a good neighborhood. But in reality, they're suffocating. They had big dreams, and middle age is choking those ambitions to death. The couple hopes maybe a move to Paris can solve their problems, but as they soon discover, dreams are just wishes that rarely come true.

The whole film is filled with a sense of "hopeless emptiness," as their plans to escape to Paris begin falling apart. They scream at each other, look for comfort in the arms of other people, and wither under the all-knowing eye of their very own mad prophet (a wonderfully fidgety Michael Shannon) who sees right through them. We watch the last bit of their relationship disintegrate before our eyes as they give up on their dreams, and by the time April makes a drastic decision, we've bought our own ticket to Paris so we can escape this depressing romance gone wrong.

The saddest superhero movie ever made

Super stars Juno and Dwight Schrute, and it was directed by the guy who made the Guardians of the Galaxy movies. So on paper, it doesn't really sound like a depressing film. You go in expecting some laughs, but underneath all the blood, black comedy, and oddly fitting supersuits, this is the saddest superhero movie ever made.

With James Gunn behind the camera, Rainn Wilson plays Frank Darbo, a guy who only has "two perfect memories" to "offset a life of pain." One of those memories was helping the police catch a criminal. The other is the day he got married to Sarah (Liv Tyler), a recovering addict and the woman of his dreams... who just left him for a smarmy drug dealer (Kevin Bacon).

That perfect memory now tarnished, Frank's life loses all meaning, and that leads to maybe the most upsetting depiction ever filmed of a man ugly crying. The whole movie is haunted by this scene, of Frank telling God how much he hates himself and his life. So when he finally dons a mask and declares himself to be the Crimson Bolt, it's only because his life is such a meaningless void that he's got to bash some people with a monkey wrench.

And if you can get past all the moments when Frank is humiliated and broken by the world, then you'll most likely walk away in the film's final gunfight, which is so upsetting that an offended Roger Ebert spoiled the moment in the first paragraph of his review. We think Super is an incredible movie, but you'll have to summon some genuine super strength to make it to the end credits.

A real life story that will leave you reeling

Dallas Buyers Club is a rough film. Moviegoers are tempted to turn it off from the moment Matthew McConaughey appears, with his sunken eyes and stick-thin body. The actor lost almost 50 pounds for the part, and he looks like he might blow away at any second. He's playing Ron Woodruff, a rodeo rider with HIV/AIDS, and the moment he gets his diagnosis, his eyes go wide with terror. The film is set in 1985, after all, and back then, AIDS was a guaranteed death sentence.

Desperate and afraid, Ron begins searching for experimental drugs to prolong his life, and you can feel his fear as he pleads with medical professionals to forget the rules and help him survive. Friends turn on him, his body is withering, and with every pound that disappears, it gets more tempting to turn the film off. McConaughey brings enough charm and humor to the role that it keeps us tagging along as he smuggles drugs up from Mexico. But we really start to reconsider our viewing choices once he befriends Rayon.

Played by Jared Leto, Rayon is a transwoman on death's doorstep, but she manages to break through Ron's bigotry. The two soon form a friendship, and that bond sets up some of the biggest tears in the film, like the moment Ron sticks up for Rayon against a transphobic jerk. The scene when Rayon visits her hateful father is hard to sit through, and when a terrified Rayon moans, "I don't want to die," it's a tragic reminder of what it was like to live in those scary times.