| Death Letter Blues | Geoff & Maria Muldaur | 6:15 | ||
| Western Stars | k.d. lang | 3:15 | ||
| Tears Only Run One Way | Robbie Fulks | 2:49 | ||
| The Man Who Couldn't Cry | Loudon Wainwright III | 6:15 | ||
| Montgomery in the Rain | Steve Young | 4:28 | ||
| Creosote | Son Volt | 4:12 | ||
| Rain Roll In | Eilen Jewell | 2:47 | ||
| I've Been Gone | Zoe Muth and the Lost High Rollers | 4:28 | ||
| Thinking About You | Jimmie Dale Gilmore | 3:16 | ||
| Red Bird | Terry Allen, The Panhandle Mystery Band | 4:22 | ||
| I Don't Know Anybody in This Town | Greg Brown | 3:27 | ||
| Braver Newer World | Jimmie Dale Gilmore | 5:00 | ||
| If I Can't Trust You with a Quarter (How Can I Trust You with My Heart?) | Zoe Muth and the Lost High Rollers | 5:07 | ||
| Enjoy Yourself | Todd Snider | 3:27 | ||
| Tonight I Think I'm Gonna Go Downtown | The Flatlanders | 2:41 |