| # | Title | Artist | Length |
|---|
| 1 | Sunday Morning Coming Down | Kris Kristofferson | 5:20 |
| 2 | Hobo's Meditation | Emmylou Harris & Linda Ronstadt | 3:18 |
| 3 | Homeless | Guy Clark | 4:24 |
| 4 | Sam Stone | John Prine | 4:16 |
| 5 | Deportee (Plane Wreck at Los Gatos) | Nanci Griffith | 5:21 |
| 6 | Man of Constant Sorrow | Dwight Yoakam | 4:16 |
| 7 | Bloody Mary Morning | Willie Nelson | 2:48 |
| 8 | The Ballad of Hollis Brown | Tony Joe White | 0:03 |
| 9 | Blue Wind Blew | Townes van Zandt | 2:39 |
| 10 | I'm So Lonesome I Could Cry | Jimmie Dale Gilmore | 3:40 |
| 11 | CCKMP | Steve Earle | 4:31 |
| 12 | Stagger Lee | The Youngbloods | 3:17 |
| 13 | Darkest Hour Is Just Before the Dawn | Emmylou Harris | 3:25 |
| 14 | When Will You Ever Come Down | Allison Moorer | 2:38 |
| 15 | El Paso | Michael Martin Murphey | 4:52 |
| 16 | Well, Well, Well | John Sebastian | 2:23 |
| 17 | Dying Boy's Prayer | Dudley Connell | 4:02 |
| 18 | The Death of Floyd Collins | Ronnie Hawkins | 3:06 |
| 19 | Folsom Prison Blues | Jerry Lee Lewis | 3:41 |
| 20 | T for Texas | The Everly Brothers | 3:31 |
| 21 | Banks of the Ohio | Ed McCurdy | 2:04 |
| 22 | When I First Came to This Land | The Limeliters | 3:19 |
| 23 | Long Black Veil | John Anderson | 3:14 |
