Guy Cry Cinema

5 Prison Movies That Make Guys Cry

Guy Cry Green Mile

There have been plenty of tough prison movies, but some have emotional story lines or endings. Even guys can’t help but get a little teary.

The goal of this series is to show that being “manly” and being disconnected with your emotions do not necessarily go hand-in-hand. While the approach to these articles is one of comedy and satire, the emotional core of these movies is very valid. Manly movies often times have the potential to make guys cry, for example:

“Prison Movies”

If there’s one thing that gets guys excited about a movie, it’s seeing the main character either think or punch their way out of a situation. Between the excitement of seeing the antagonist thwarted and the escapism of pretending it’s the audience doing the outsmarting/punching, defeating an external foe is good manly movie fodder. When we look at prison movies, the external foe is literally everything. The guards are the foe, the walls are the foe, even the daily routine is the foe. With such insurmountable odds all around, the defeat of the foe is all the more cathartic. A great prison movie doesn’t necessarily have to include an escape in the literal sense; even retaining your mental freedom in such an oppressive local is a win. But with every win comes with a cost, and every cost carries the potential for tears.

1. The Green Mile

One of the two Stephen King prison films on this list, and you’d think that list would be shorter. This film has a perfect mixture of real-world drama and mystical magic to keep any viewer enthralled. Some watch for Michael Clarke Duncan’s amazing portrayal of a simple man who’s framed for murder and may be some sort of wizard. Others watch to see bees (flies?) shoot out of a magic giant man. Whatever your poison, this film shows that while not all guards in prison are mean, neither are all prisoners.

There’s a moral dilemma that occurs in this film, in the character played by Tom Hanks. Throughout the film it’s made crystal clear not only that Michael didn’t do the crime, but that he has miracle powers. As not-corrupt as Tom is, he still has to follow the system that he’s a part of. Michael is still put to death, but not before “cursing” Tom with extended life to suffer the guilt of destroying an according-to-Hoyle miracle merely because it’s his duty. My first response is “Hey, Tom was a good guy, how come he gets cursed?” and then I remember Michael was a good guy who got punished too. Then I get sad. 

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2. The Shawshank Redemption

The film that makes up 50% of all TNT viewing schedules, this is a fantastic movie. Andy Dufresne (pronounced Doofrain) is also put in prison for a crime he didn’t commit. While there he meets prison friends, fights off rape and prison corruption, builds a lovely chess set, and crawls through poo water to freedom. The interesting part about this movie is that although it ends with a prison break, the main plot thread is not escaping. If anything it’s a story about the world trying to break Andy and failing to do so. Now THAT’S what guys like to see. 

The film’s intense oppressive vibe really weights on the viewer. Andy is attacked by a rape gang, and we’re told in no uncertain terms that he didn’t always win the fight. A new prisoner comes who can prove Andy’s innocence, and is murdered by the guards to keep Andy in prison. But the most depressing part is Brooks. Brooks was in prison so long that he lost the ability to operate without it. Once released, he hung himself. This unseen foe of entropy is the scariest part of this film in my opinion. Andy can steel himself from abuse, retreat into his mind when punished, and plan his escape all he wants – but if he takes too long, the invisible enemy of entropy will win. Eventually he will lose the ability to resist, and seeing what that looks like in Brooks was heartbreaking. 

3. Cool Hand Luke

This film is the source of the famous line “What we’ve got here is a failure to communicate.”  It could also be titled “Paul Newman gets beaten up and eventually killed” because that’s what happens. Sure, he retains his mental freedom, but his multiple escape attempts were less than successful when compared with Andy from Shawshank. And his continued escapes, all of which lead to the most severe punishments, show Luke as an unstoppable force of free will and free thought. But he’ll never be a free man again. The film never deludes us that Luke’s hijinks are exactly that…shenanigans to prove that he’s still a man and not just a husk of one.

The sad part for me is the fact that he not only doesn’t escape, but doesn’t escape regardless of the predictable, formulaic movie logic that builds up around him. You watch a movie with such a charismatic character as Luke, and when he learns that his mother had died you think “Oh, he’s totally going to escape, cause now he has a reason.” But no, he kinda makes it out but is then captured again and tortured. If we complain that current movies treat us all like children and condition us to expect a happy or balanced ending, this movie will make you expect the worst. 

4. Escape from Alcatraz

Remember when Clint Eastwood was an action star, instead of a crazy old man and an overrated director? This film does.  Based on true events, Clint plays a man who may or may not have been part of the only escape from Alcatraz. The ambiguity is that the real prisoner might have drowned, though a body was never recovered. It’s a well-made “escape from prison” movie, and really the prototypical one. The successful use of paper-mache dolls to fool the guards makes me wonder if this truly was the only successful escape, though. I mean, who knows how long some guys might be gone?

Yes it was based on a true story and the escapees were actual big fat criminals who deserved to be locked up on The Rock. That doesn’t make the fact that Butts (yes, his name was Butts) backed out of the escape at the last moment any less disheartening. As much as Clint may have survived, Butts would have made it just as far. It’s like that “Twilight Zone” episode where the old fogies kick a can and become young, but the cranky old man who didn’t participate stays old. Like Butts, he was close enough to touch what he wanted more than anything, and his reluctance was perfectly understandable. That’s somehow more sad than the idea that the Man With No Name drowned in icy cold water less than half a mile from civilization. 

5. The Great Escape

Remember when I said a good prison movie doesn’t necessarily need an escape in it? Well this film’s the exception. The whole film is built around escaping, more so than even Escape from Alcatraz. The prison in this one is specifically to house previous escapees, and the jailers are Nazis during WWII. 

This thing that makes this film hard to watch with dry eyes is the scope of the failure. This film  doesn’t focus on one man trying to fight the power, but a group trying to free 250 people from the enemy. Fast forward to the end, and only three escaped. After so much careful planning, faking documents, and throwing together the resourceful brains of everyone involved the majority gets out briefly only to be recaptured and shot. Even Steve “Cooler Than Everyone Ever” McQueen was thrown back in prison after his extensive “motorcycling across Europe” plan. Sure, we hear him throwing his baseball in the end, suggesting he hadn’t been mentally beaten and the triumph of his spirit will get him there some day, but 3 out of 250 escaping and not one of them is the main character? It’s tough to call that a win. 

Like what you see? Secure enough in your masculinity for more? Check out more Guy Cry Cinema or watch Dan on No Right Answer, the weekly debate show that knows what’s really important: Pointlessly arguing about geek culture.


About the author

Daniel Epstein
Father, filmmaker, and writer. Once he won an Emmy, but it wasn't for being a father or writing.