I have an affinity for prison songs and Merle Haggard wrote some of the best. He did time in various California correctional institutions before making it as a Country Music star. His Sing Me Back Home was a masterpiece, IMO, and was covered by a lot of folks but I always go for the Flying Burrito Brothers recording from their first album in large part because of Sneaky Pete Kleinow's pedal steel guitar playing on it. Sing Me Back Home
Another Haggard classic is Mama Tried and my favorite version is by the good old Grateful Dead off of their epic live album nicknamed "Skull and Roses" (they wanted to call the LP "Skull Fuck" but Warner Bros. wouldn't go for it).Mama Tried

I was surprised to find out recently that another favorite, 99 Years and One Dark Day, was written by Jesse "Lonecat" Fuller, the one man band who gave us San Francisco Bay Blues, The Monkey and the Engineer, Frisco Bound and others. I've been singing it since I first heard it at a Hot Rize concert long ago. Tim O'Brien, Hot Rize' lead singer and mandolin player, arranged it and sang it on their Hot Rize LP released in 1979. 99 Years and One Dark Day