| # | Title | Artist | Rating | Length |
|---|
| 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 | | 2:56 |
| 4 | The Taker (live) | Ryan Bingham | | 2:48 |
| 5 | The Captive (live) | Jessi Colter | | 3:07 |
| 6 | Nobody Wins (live) | Lee Ann Womack | | 3:05 |
| 7 | Jesus Was a Capricorn (Owed to John Prine) (live) | Jack Ingram | | 3:42 |
| 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 | | 3:12 |
| 12 | From the Bottle to the Bottom (live) | Dierks Bentley & The Travelin' McCourys | | 3:53 |
| 13 | Help Me Make It Through the Night (live)- recorded at:
- Bridgestone Arena in Nashville, Tennessee, United States (on 2016-03-16)
- live cover recording of:
- Help Me Make It Through the Night (on 2016-03-16)
- lyricist and composer:
- Kris Kristofferson
- publisher:
- BMG Songs Ltd., Combine Music Corp., EMI Songs Australia Pty. Ltd., EMI Songs Ltd., Keith Prowse Music Publishing Co. Ltd. and KPM
- sub-publisher:
- Air Music Scandinavia AB
- cover recording of:
- Help Me Make It Through the Night
- lyricist and composer:
- Kris Kristofferson
- publisher:
- BMG Songs Ltd., Combine Music Corp., EMI Songs Australia Pty. Ltd., EMI Songs Ltd., Keith Prowse Music Publishing Co. Ltd. and KPM
- sub-publisher:
- Air Music Scandinavia AB
| Lady Antebellum | | 4:10 |
| 14 | Under the Gun (live) | Darius Rucker | | 4:13 |
| 15 | For the Good Times (live)- recorded at:
- Bridgestone Arena in Nashville, Tennessee, United States (on 2016-03-16)
- live recording of:
- For the Good Times (on 2016-03-16)
- lyricist and composer:
- Kris Kristofferson
- publisher:
- Careers Music, Inc., Careers-BMG Music, Careers‐BMG Music Publishing, Universal Music Publishing International MGB Ltd., Universal Music Publishing MGB Ltd., Valentine Music Ltd. and Universal Music Careers (in 1968)
- cover recording of:
- For the Good Times
- lyricist and composer:
- Kris Kristofferson
- publisher:
- Careers Music, Inc., Careers-BMG Music, Careers‐BMG Music Publishing, Universal Music Publishing International MGB Ltd., Universal Music Publishing MGB Ltd., Valentine Music Ltd. and Universal Music Careers (in 1968)
| Alison Krauss & Jamey Johnson | | 4:23 |
| 16 | Casey’s Last Ride (live) | Alison Krauss | | 3:57 |
| 17 | If You Don’t Like Hank Williams (live) | Hank Williams, Jr. | | 3:09 |
| 18 | To Beat the Devil (live) | Eric Church | | 6:45 |
| 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 |