| # | Title | Artist | Rating | Length |
|---|
| 1 | Border Lord | Kris Kristofferson | 4 | 3:37 |
| 2 | The Sabre and the Rose | Kris Kristofferson | | 5:13 |
| 3 | Broken Freedom Song | Kris Kristofferson | 4 | 5:24 |
| 4 | Jesus Was a Capricorn | Kris Kristofferson | 4 | 2:28 |
| 5 | Shandy (The Perfect Disguise) | Kris Kristofferson | | 3:39 |
| 6 | Sugar Man | Kris Kristofferson | 4 | 4:01 |
| 7 | The Last Time | Kris Kristofferson | | 4:11 |
| 8 | Nobody Wins | Kris Kristofferson | 5 | 3:06 |
| 9 | I’d Rather Be Sorry | Kris Kristofferson, Rita Coolidge | 3.5 | 3:10 |
| 10 | Highwayman | Kris Kristofferson, Waylon Jennings, Willie Nelson, Johnny Cash | | 3:03 |
| 11 | Don’t Cuss the Fiddle | Kris Kristofferson | 3.5 | 3:24 |
| 12 | The Bigger the Fool, the Harder the Fall | Kris Kristofferson | | 3:32 |
| 13 | Stranger | Kris Kristofferson | | 3:08 |
| 14 | If You Don’t Like Hank Williams | Kris Kristofferson | 3 | 3:29 |
| 15 | Here Comes the Rainbow Again | Kris Kristofferson | | 2:54 |
| 16 | Once More With Feeling | Kris Kristofferson | | 2:50 |
| 17 | How Do You Feel About Foolin’ Around | Kris Kristofferson, Willie Nelson | | 2:54 |
| 18 | Why Me | Kris Kristofferson | | 3:27 |
| 19 | Please Don’t Tell Me How the Story Ends | Kris Kristofferson | | 2:38 |
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