| Title | Performer | Writers | Original release |
|---|
| 1. | "Border Lord" | Kris Kristofferson | Kristofferson, Stephen Bruton, Donnie Fritts, Terry Paul | From the album Border Lord (Monument, 1972) |
| 2. | "The Sabre and the Rose" | Kris Kristofferson | Kristofferson | From the album Easter Island (Monument, 1978) |
| 3. | "Broken Freedom Song" | Kris Kristofferson | Kristofferson | From the album Spooky Lady's Sideshow (Monument, 1974) |
| 4. | "Jesus Was a Capricorn (Owed to John Prine)" | Kris Kristofferson | Kristofferson | From the album Jesus Was a Capricorn (Monument, 1972) |
| 5. | "Shandy (The Perfect Disguise)" | Kris Kristofferson | Kristofferson | Spooky Lady's Sideshow |
| 6. | "Sugar Man" | Kris Kristofferson | Kristofferson | Jesus Was a Capricorn |
| 7. | "The Last Time" | Kris Kristofferson | Kristofferson | From the album To the Bone (Monument, 1981) |
| 8. | "Nobody Wins" | Kris Kristofferson | Kristofferson | Jesus Was a Capricorn |
| 9. | "I'd Rather Be Sorry" | Kris Kristofferson & Rita Coolidge | Kristofferson | From the album Breakaway (Kris Kristofferson & Rita Coolidge, Monument, 1974) |
| 10. | "Highwayman" | The Highwaymen (Kris Kristofferson, Waylon Jennings, Willie Nelson & Johnny Cash) | Jimmy Webb | From the album Highwayman (The Highwaymen, Columbia, 1985) |
| 11. | "Don't Cuss the Fiddle" | Kris Kristofferson | Kristofferson | From the album Who's to Bless and Who's to Blame (Monument, 1975) |
| 12. | "The Bigger the Fool, the Harder the Fall" | Kris Kristofferson | Kristofferson, Bruton, Michael Utley | Easter Island |
| 13. | "Stranger" | Kris Kristofferson | Kristofferson | Who's to Bless and Who's to Blame |
| 14. | "If You Don't Like Hank Williams" | Kris Kristofferson | Kristofferson | From the album Surreal Thing (Monument, 1976) |
| 15. | "Here Comes that Rainbow Again" | Kris Kristofferson | Kristofferson | From the album The Winning Hand (Kris Kristofferson, Willie Nelson, Dolly Parton & Brenda Lee, Monument, 1982) |
| 16. | "Once More with Feeling" | Kris Kristofferson | Kristofferson, Silverstein | From the album Shake Hands with the Devil (Monument, 1979) |
| 17. | "How Do You Feel About Foolin' Around" | Kris Kristofferson & Willie Nelson | Kristofferson, Bruton, Utley | From the soundtrack album Music from Songwriter (Kris Kristofferson & Willie Nelson, Columbia, 1984) |
| 18. | "Why Me" | Kris Kristofferson | Kristofferson | Jesus Was a Capricorn |
| 19. | "Please Don't Tell Me How the Story Ends" | Kris Kristofferson | Kristofferson | From the album The Austin Sessions (Atlantic, 1999) |
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