All Time Favorite Prison Movies

It seems fitting on the day after “The Oscars” to talk about movies. Last week, my husband and I watched an old favorite of ours on Netflix. It was “Escape from Alcatraz” with Clint Eastwood. This led to a discussion of our favorite prison movies. Now, if someone had asked me if I liked prison movies, I probably would have said something like…”Not particularly”. Imagine how surprised I was to realize that some of my favorite movies are prison based. I made a list. I’m willing to bet that some of these could be on your favorites too. You might even think of some that I missed.


So here goes- my favorite prison movies:

1. “The Shawshank Redemption” – this has got to be my all time favorite. It has a stellar acting team, a fantastic plot (innocent man found guilty), an unbelievable escape, characters you love to hate, a perfect get even moment, the good guys being evil and vice versa, and a suspenseful story twist you just aren’t expecting. It even has a happy ending. This is as close to perfection as storytelling gets.

2. “Cool Hand Luke”- this is a close tie with #3 for me. If you are in the younger generation and have never seen this movie, you are missing out. Paul Newman stars as an irrepressible young con driving the “man” crazy and becoming a legend to his fellow inmates. Most quotable line-“It seems that what we have here is a failure to communicate.” Newman was outstanding in this role.

3. “The Green Mile”- again, a stellar cast, unforgettable characters, good guys and bad guys on both sides of the bars and a story that leaves you breathless. I end up sobbing every time I watch it. This movie too is close to perfection.

4. “Brubaker”- Robert Redford stars in this seventies gem as a new warden of a very corrupt southern prison system. If I remember correctly, this movie was based on a true story. Best beginning ever, Brubaker enters his prison as an inmate to see first hand the mistreatment of prisoners. Then when a near riot ensues, an inmate is clamoring to see the warden and he identifies himself to both the jailors and the jailed. Great “Oh, s..t!” moment.

5. “Con Air” – this one has the best action scenes, a twisting, suspenseful plot and riveting evil people. This movie is one wild ride and hanging on for dear life applies to viewers as well as convicts. I find myself watching this one when I’m angry and want to see people “getting what’s coming to them”. It’s great therapy! I love the “never leave a man behind” theme.

6. “Escape from Alcatraz”- I think this pioneered the good guys/ bad guys being on both sides of the bars. Is it possible to hate anyone more than we hate the warden as he takes Doc’s painting privileges away? I don’t think so.

7. “The Longest Yard” – I like the Adam Sandler version of this best which is unusual for me. I tend to dislike remakes and I’m not a huge Sandler fan but the rest of the cast in his movie makes it. Standout prison types, a good funny man, and a resurrected Burt Reynolds make this a fun one.

8. “Papillon” – this is another old classic worth digging up and watching. Steve Mcqueen and Dustin Hoffman give amazing performances illustrating the downfall and breaking of the spirit of man. This, too, is based on truth and one man’s determination to be free no matter the cost.



We couldn’t decide if the next three movies are more war movies than prison movies but we thought they deserved a shout out; “The Dirty Dozen”, “The Great Escape” and “Bridge over the River Kwai”. We love all three.

So why do we love these movies? I think because we are reminded that people are people even when being treated as animals. And that no matter our circumstances we all still have that one great choice to make- who are we going to be? Also, we love to root for the underdog and we love it even more when he wins at the expense of “the man” whom we love to hate. Especially when that win involves someone who has refused to let his spirit be broken. That’s the view from my side of the street, what’s yours?