| 1 | Please Don’t Tell Me How the Story Ends (live) | Buddy Miller | 4:10 |
| 2 | Kristofferson (live) | Jon Randall, Jessi Alexander & Larry Gatlin | 3:04 |
| 3 | Here Comes That Rainbow Again (live) | Martina McBride | 2:55 |
| 4 | The Taker (live) | Ryan Bingham | 2:47 |
| 5 | The Captive (live) | Jessi Colter | 3:07 |
| 6 | Nobody Wins (live) | Lee Ann Womack | 3:04 |
| 7 | Jesus Was a Capricorn (Owed to John Prine) (live) | Jack Ingram | 3:41 |
| 8 | Worth Fighting For (live) | Jennifer Nettles | 5:01 |
| 9 | Loving Her Was Easier (Than Anything I’ll Ever Do Again) (live) | Rosanne Cash | 3:25 |
| 10 | Chase the Feeling (live) | Emmylou Harris & Rodney Crowell | 3:42 |
| 11 | The Pilgrim: Chapter 33 (live) | Kris Kristofferson & Emmylou Harris | 3:11 |
| 12 | From the Bottle to the Bottom (live) | Dierks Bentley & The Travelin' McCourys | 3:53 |
| 13 | Help Me Make It Through the Night (live) | Lady Antebellum | 4:09 |
| 14 | Under the Gun (live) | Darius Rucker | 4:13 |
| 15 | For the Good Times (live) | Alison Krauss & Jamey Johnson | 4:22 |
| 16 | Casey’s Last Ride (live) | Alison Krauss | 3:56 |
| 17 | If You Don’t Like Hank Williams (live) | Hank Williams, Jr. | 3:08 |
| 18 | To Beat the Devil (live) | Eric Church | 6:44 |
| 19 | Me and Bobby McGee (live) | Reba McEntire | 4:21 |
| 20 | Sunday Mornin’ Comin’ Down (live) | Kris Kristofferson & Willie Nelson | 4:29 |
| 21 | Why Me (live) | Kris Kristofferson | 4:41 |