| # | Title | Artist | Rating | Length |
|---|
| 1 | The Pilgrim: Chapter 33 | Emmylou Harris, Sam Bush, Jon Randall, Byron House & Randy Scruggs | | 3:51 |
| 2 | Maybe You Heard | Todd Snider | | 3:30 |
| 3 | The Circle | Marta Gómez | | 4:21 |
| 4 | Lovin' Him Was Easier (Than Anything I'll Ever Do Again) | Rosanne Cash | | 3:38 |
| 5 | Come Sundown | Rodney Crowell | | 3:17 |
| 6 | For the Good Times | Lloyd Cole & Jill Sobule | | 3:26 |
| 7 | Jesus Was a Capricorn | Marshall Chapman | | 3:53 |
| 8 | The Silver Tongued Devil & I | Shooter Jennings | | 5:09 |
| 9 | Sunday Mornin' Comin' Down | Gretchen Wilson | | 6:01 |
| 10 | Sandinista | Patty Griffin & Charanga Cakewalk | | 4:14 |
| 11 | Darby's Castle | Russell Crowe & The Ordinary Fear of God | | 3:59 |
| 12 | Me and Bobby McGee | Brian McKnight | | 5:01 |
| 13 | Smile at Me Again (instrumental) | Randy Scruggs | | 2:44 |
| 14 | The Captive (feat. Vance Haines) | Jessi Colter | | 3:55 |
| 15 | Help Me Make It Through the Night | Bruce Robison & Kelly Willis | | 3:05 |
| 16 | Why Me | Shawn Camp | | 3:36 |
| 17 | The Legend | Willie Nelson | | 6:32 |
| 18 | Please Don't Tell Me How the Story Ends | Kris Kristofferson | | 3:15 |
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