THE BEST PRISON MOVIES OF ALL TIME

Check out and consider this guide a quick reference in order to try out a prison movie you may otherwise would have never given a crap about.

FOR DRAMA

1. The Shawshank Redemption (1994) Of course this is usually at the top of any prison movie list. Not only that, but perhaps even ranking as one of the greatest movies of all time. Relationships and redemption, I mean come on, that’s some powerful stuff. If you must see one movie on this list, it would be this. I always viewed it as a sort of Disney-esque movie with a bit of a twisted, dark undertone lurking in the background. Watch it…. you’ll see what I mean.
2. Midnight Express (1978) The opening minutes set the tone for this nightmarish experience, and what you come away with is an unforgettable movie. That and DON’T EVER SMUGGLE DRUGS OUT OF THE COUNTRY KIDS.
3. American History X (1998) Edward Norton is a skinhead who becomes lost going down life’s dark paths, all while still keeping his little brother from following the same tragic one. An incredible movie with great acting and directing, and I rank it as one of the best.
4. Cool Hand Luke (1967) The hell with prison, right? Paul Newman is a Florida prisoner who marches to the beat of his own drummer and is well…. cool. Who’s gonna win, him or the a-hole warden?
5. The Old Man and The Gun (2018) I watched this with high expectations, as it had been a while since I saw a good bank robber/prison escapee movie, and I tell you it exceeded my expectations. You follow the career of smooth and charming criminal Forrest Tucker (Robert Redford) in his chosen profession.
6. Escape From Alcatraz (1979) Clint Eastwood in his acting prime as he plans an escape from the inescapable. Did he escape? Did he die? Who the hell knows. Nail biting and tense though.
7. The Green Mile (1999) Although it’s a pretty good movie, I’d probably watch this film only once in my lifetime. If you have the patience and the bladder to endure the grueling length (3 hours), you’ll come away appreciating it more if you were a little high. Just sayin.
8. An Innocent Man (1989) Tom Selleck’s mustache gets incarcerated under false pretenses in this drama/thriller. Now I know this film would hardly qualify to stand up to other powerful films on this list, but I really don’t care. It’s my list, I loved the 80’s, liked this movie, and can do what I want…. so screw off.

FOR COMEDY

1. Stir Crazy (1980) When comedians look to and talk about what had inspired them to be comedians, you hear one name more than any other: Richard Pryor. Look him up kids. One of the best duos was pairing him opposite Gene Wilder. Now just add prison into the equation and you have comedy gold.
2. Get Hard (2015) Kevin Hart and Will Ferrell do stupid shit with lots of prison cliches thrown in, but nonetheless something decent that doesn’t require a lot of thinking.
3. Madea Goes To Jail (2009) What can I say…. Watching this movie at times feels like a real punishment, however there are a handful of funny scenes, and at times it’s so bad it’s good.

FOR DRAMEDY

1. I Love You Phillip Morris (2009) I was watching one of my favorite shows (I Almost Got Away With It), and saw the interview they did with Steven Russell. I was fascinated with his passion for life, love, and the ingenuity to preserve all of it at whatever cost. Intrigued, I searched for it, and lo and behold, it was on Netflix at the time. It’s incredibly entertaining to watch Jim Carrey portray Russell, and the lengths he went to. Check it out, you’ll like it.
2. The Longest Yard (1974) This isn’t the pile of s*** Sandler put out some years back, this is the good one. The one with classic 1970’s Burt Reynolds as an ex-football star turned prisoner, turned prisoner football star. Classic.
3. Out of Sight (1998) Smooth, yet (un)successful bank robber Jack Foley (George Clooney) falls for someone on the other side of the law, Federal Marshall Karen Sisco (Jennifer Lopez). I mean, if you’re gonna screw up your life and fall in love with a Federal Agent, might as well be J-LO. A great prison crime caper.

FOR ROMANCE

1. Labor Day (2014) When you think of romantic movies, prison is not the first thing that necessarily comes to mind. Who the hell knows, maybe it does. I won’t judge you. Anyways, I searched for other movies to put in this genre and really couldn’t find them, but I wanted to find a place for this one as I really liked this movie. But beware though, this movie can definitely invoke a lot of emotions, especially if you’re sitting there with your significant other, and having endured some legal setbacks. You’ve been warned…. and yes, if you cry like a little bitch at the end, you should get a pass.

FOR ACTION

1. Con air (1997) A great Nicholas Cage movie, and quite honestly my favorite. Long before he lost his mind and went crazy, he made a few good films. High jinks ensues when an airplane full of criminals take over a flight en route to a new supermax. Good times.
2. The Next 3 Days (2010) Even though critics bashed this film, I really, really enjoyed it. Russel Crowe is always amazing, and he plays a single dad raising his son after his wife is convicted of murder and sent to prison. Awe shucks. After years of exhausting appeals and having no other option, he does what any good family man would do…. break her out of prison. Check it out.

FOR DOCUMENTARY

1. The Survivors Guide to Prison (2018) A little bit of a different and unique feature length film with some great info for anybody out there wanting a glimpse into just how messed up the system is. Best advice: DON’T GO TO PRISON. You can check this one out on Netflix.
2. 13th (2016) The beauty of the American prison industry are on full display, complete with racial inequality and injustice. Yeah, I’m being sarcastic. Just try watching this without getting pissed off at the system. That and throwing the remote at the tv.
3. Long Shot (2017) Now although the running time (39 mins) doesn’t necessarily qualify it as a full length film, I have to say I loved it. Follow Juan Catalan, the gaping holes in the criminal justice system, and the hit show Curb Your Enthusiasm for an unbelievably true story.

FOR INDIE

1. Shot Caller (2017) So I was messing around on Amazon Prime, and I discovered this bad ass flick. When I read the title and the premise I thought this was gonna be something stipid I’d fast forward through, and turn off after a few minutes. I didn’t. Better yet, I really, really liked it. Although it can be a little bleak at times (hey, so is life), it was a great prison movie you should see.
2. Brawl in Cell block 99 (2017) Based off the stupid title and cover when I rented it on Redbox, I thought this was gonna be some garbage. However, it was like a Christmas morning discovering this little gem. I was pleasantly surprised at the steady amount of gratuitous violence and strong language dosed throughout the film, making you want more. I was especially pleased at the different role Vince Vaughn takes being a former boxer turned drug courier turned ass-kicking machine thrown in prison.
3. Bad Boys (1983) No, this isn’t the one you’re thinking of. No Will Smith, No Martin Lawrence, No Miami backdrop. Just a bunch of juvenile delinquents cramped together in lock up beating each other’s ass up for supremacy. Also starring Sean Penn…. Oh yeah, you’re going to like this one.
4. Bronson (2008) I love me some Tom Hardy, and the transformation he goes through to portray Charles Bronson, (Britain’s most feared and violent prisoner) is quite intense. This based on a true story is one part beauty, one part psychotic, but all enjoyable.
5. O.G (2018) HBO generally makes really good movies, and this was no exception. I loved Jeffrey Wright on Boardwalk Empire (HBO), and even more as Louis Menkins (The O.G.). He captures the hesitation and nervousness of a prisoner on the eve of being released from a 24 year prison sentence, and all the emotional baggage that comes with.

HONORABLE MENTIONS

BEST BANK ROBBERY MOVIE (WHICH LEADS TO PRISON)

1. HEAT (1995) Hollywood kingpins Robert De Niro and Al Pacino play cat and mouse in Michael Mann’s phenomenal ode to taking scores. All star cast here with so much great dialogue and action scenes that you even forget the movie runs almost 3 hours.
2. The Town (2010) For some reason beyond me, I can watch this movie over and over, yet never get tired of it. It’s so very bow-sten. It’s a thrilling and intense ride as you follow the lives of professional bank robbers and the choices they make moving forward.
3. The Place Beyond the Pines (2012) Although it’s a bit tragic, I still loved, loved this movie. Ryan Gosling, Bradley Cooper, Eva Mendes. I mean come on. Anyways, a story about family, relationships, kids, and consequences for your actions. This movie can definitely be heavy on the heart. Once again, you’ve been warned.
4. Set It Off (1996) I remember watching this movie high as a kite, and it didn’t disappoint. Now some of the reviews I’ve read have not been very favorable, making me question if it was what I smoked, the movie being good, or a combination. Either way I would try the combo to see for yourself.
5. Hell or High Water (2016) This movie didn’t get a lot of hype when it was released, yet I checked it out and thought it was pretty good. Bank robbing brothers in the mid-west who are trying to save their family land from foreclosure. Awe, how sweet. Don’t worry, it’s still awesome.

There you have it. Sit back, get comfy, and give these prison flicks a watch.

–The Educated Felon