Fortunately there are some really excellent movies on this subject.
In this category four films rise to the top.
1 - Cool Hand Luke - This is my favorite Paul Newman film (and there are a bunch of great Newman films - like Butch Cassidy, Hud, The Hustler, Torn Curtain, Cat on A Hot Tin Roof and Exodus). He was nominated for best actor but Rod Steiger won the award for the film In The Heat of the Night. Well deserved but a tough call still. 1967 was a pretty strong Best Actor year with Dustin Hoffman (The Graduate), Warren Beatty (Bonnie & Clyde) and Spencer Tracy (Guess Who's Coming to Dinner). Newman only ever won one Oscar; Best Actor in The Color of Money. "Takin' it off here boss" is a well-known phrase from the film that has endured over many years as is "What we have heyah is a failyuh ta communicate." And, the hard boiled egg sequence would be in contention for best all-time individual scenes. (Trailer)
2 - Shawshank Redemption - This movies could just as easily be number one on my list. By far, Morgan Freeman's best work. Tim Robbins also did a terrific job in this film. It was nominated for 7 Oscars, including Best Actor and Best Picture. And, this movie is rated #1 on IMDb's Top 250 List. One of the few where almost the entire picture takes place in the prison. This film can be watched several times. (Trailer)
3 - Midnight Express - The first 15 minutes of this film are as heart pounding as you will ever see. They even use a beating heart as part of the soundtrack and it really works. If you weren't convinced before that foreign prisons are not a great place to hang out, you will be after seeing William Hayes (try pronouncing it the way the Turks do) in there for a while. (Trailer) Excellent soundtrack and theme song. Whatever happened to star Brad Davis (maybe top 10 for One Hit Wonders in the movies)?
4 - The Green Mile - This film is a bit unusual for a prison movie. But it is powerful. Tom Hanks performs beautifully as the righteous southern prison guard. Nominated for four Oscars, including Best Picture. I think the most memorable line is "Coffey...just like the drink only spelt different." Michael Duncan does a fabulous job as John Coffey and somehow they make him seem 7 feet tall from every angle. (Trailer)
The remaining films getting 5 to 10 ;-) are:
Carandiru - Subtitle alert - but worth it. The most brutal prison in Brazil, through the eyes of an AIDS doctor. VERY intense movie.
Papillion - Steve McQueen as Henri Charrier, The Butterfly. And, Dustin Hoffman as his compatriot, Louis Dega. See Steve run and run and run. Seems very realistic in terms of the conditions they must have endured. And, watch out for that self-abuse stuff; it can be very dangerous.
Murder in the First - Christian Slater, Gary Oldman, William Macy and Kevin Bacon (another excellent one for the Seven Degrees game) in a very creepy film. Based on a true story that led to the closing of Alcatraz.
Dead Man Walking - Susan Sarandon gets the Best Actress Oscar. Sean Penn also stars and Tim Robbins directed (and got nominated). The Hurricane - Denzel as Ruben "Hurricane" Carter, made somewhat more famous by the Bob Dylan tune of the same name. Outstanding song. Movie not quite as good; but it did help get the guy out of jail.
Stir Crazy - This may violate my own rule (because it is not predominantly filmed at the prison) but Pryor and Wilder are just too funny together to leave this one off the list.
Nearly got paroled but didn't make it include:
In the Name of the Father - Daniel Day Lewis in another strong performance. Where did he get that hairdo?
Brubaker - A little over-the-hill, Robert Redford plays con and warden. Somehow he is too clean cut for either part. Still entertaining.
The Last Castle - James Gandolfini is excellent as the warden. Another one with Robert Redford pretty far past his prime.
In Cold Blood - This is a chilling movie. Based (very closely) on a true and grisly story. Truman Capote wrote the book and inspired multiple movies on the subject. Robert Blake was freaky as a murderer years before he did it for real.
The Count of Monticristo - This movie has been made about 18 different times - literally. There is an animated and an anime' version, one made for TV and a mini-series; one made in 1908 and several more made in the 40's and 50's. I like the 2002 version.
Special Mention: Primal Fear - a great performance by Edward Norton, Jr., but I put this in the Courtroom Drama Category (Top 10).
Don't ask about: Escape from Alcatraz or The Birdman of Alcatraz - I just didn't like them (too slow...)
Also, Gideon's Trumpet was good but it was made for TV so it doesn't count.
And, last, The Rock. A very entertaining film with Sean Connery and Nicholas Cage, but breaking into a museum that used to be a prison doesn't qualify for this category.
