| # | Title | Artist | Length |
|---|
| 1 | Chain Gang Blues | Kokomo Arnold | 3:04 |
| 2 | Big Rock Jail | Ed Bell | 2:45 |
| 3 | He's in the Jailhouse Now | Jim Jackson | 3:01 |
| 4 | Prison Blues | Alice Moore, Ike Rodgers & Henry Thomas | 3:18 |
| 5 | Jailhouse Fire | Walter "Buddy Boy" Hawkins | 2:30 |
| 6 | Christmas in Jail - Ain't That a Pain | Leroy Carr with Scrapper Blackwell | 3:13 |
| 7 | Penitentiary Bound Blues | Sylvester Weaver | 3:04 |
| 8 | Blind Lemon's Penitentiary Blues | Blind Lemon Jefferson | 2:48 |
| 9 | Midnight Special | Lead Belly | 2:04 |
| 10 | County Jail Special | Champion Jack Dupree | 3:17 |
| 11 | The County Farm Blues | Mae Glover & James Parker | 2:41 |
| 12 | New Prison Blues | Peg Leg Howell | 3:17 |
| 13 | De Kalb Chain Gang | Fred McMullen & Curley Weaver | 3:05 |
| 14 | The County Farm Blues | Bo Carter | 3:32 |
| 15 | Alabama Prison Blues | Jesse Wadley | 2:33 |
| 16 | County Jail | Tampa Red & Big Maceo | 2:55 |
| 17 | Crime Doesn't Pay | Blind John Davis, Merline Johnson, Ransom Knowling & Bill Settles | 2:47 |
| 18 | County Jail Blues | Funny Papa Smith | 2:53 |
| 19 | Big House Bound | Blind Boy Fuller & Sonny Terry | 2:42 |
| 20 | Ninety-Nine Year Blues | Julius Daniels | 3:05 |
| 21 | Doin' a Stretch | Blind Blake & Alex Robinson | 2:39 |
| 22 | Parchman Farm Blues | Bukka White | 2:40 |
| 23 | Prisoner Bound | Bill Gaither & George "Honey" Hill | 3:04 |