John Prine recorded "Christmas In Prison" for his third album, in 1973, two years after he recorded "Paradise." In the interest of actually getting something posted today (sorry for the slack over the weekend), I won't tell you all about each individual track, but there's a decent amount of variety here, so be sure to get 'em all. As always, I recommend the zipfile.
Also, there are a lot of covers on YouTube. (1 2 3 4 5 should get you started.)
(Edited to point out that John -- and everyone else -- cusses a tiny bit in this song. If you mind blasphemy in your Christmas music, just move on to the next post. Sorry!)
Come back tomorrow for more Christmas-y prison-y songs!
John Prine 1 2
Emmy The Great and The Lightspeed Champion 1 2
Joshua James 1 2
The Boxmasters 1 2
Billy Button Band (live 12-08-06) 1 2
Rory McLeod 1 2
Honky Tonk Confidential 1 2
Doug Legacy 1 2
Will Kimbrough 1 2
The Conestokers 1 2
John Prine (live) 1 2