I thought I'd compile a list here of prison movies and documentaries that I like– just so we'd have them for the holidays. I am including material that I think adds to the discussion in some substantive way.

Documentaries
Fruitvale Station
Gideon's Army
Shakespeare Behind Bars
The House I Live In
The Dhamma Brothers
Concrete, Steel and Paint
Tattoed Tears
Titicut Follies
Attica
Well Contested Sites
 

Films
Shawshank Redemption
Somebody Has to Shoot the Picture
The Hurricane
The Green Mile
Dead Man Walking
Snitched
Conviction
Schindler's List
Stranger Inside
Short Eyes
Weeds
Caesar Must Die
Kiss of the Spider Woman
Micky B
 

Many movies I have not seen can be found here . Real Cost of Prisons Projects and Prison Photography has their list of the best docs. Films and Docs I want to see mentioned on these sites!

Herman's House
Kids for Cash
Mothers of Bedford
Women Behind Bars
Sweethearts of the Prison Rodeo
Broken on All Sides
Girlhood
Red Hook Justice
Killer Poet
Carandiru
Slam
In the Name of the Father
The Big House