Disc 1
1. Highwayman – The Highwaymen
2. Silver Stallion – The Highwaymen
3. The Greatest Cowboy of Them All – The Highwaymen
4. Take It to the Limit – Johnny Cash
5. Help Me Make It Through the Night – Waylon Jennings & Willie Nelson
6. The Taker – Willie Nelson
7. Just to Satisfy You – Waylon Jennings & Willie Nelson
8. Moment of Forever – The Highwaymen
9. Eye of the Storm – Kris Kristofferson & Willie Nelson
10. The Pilgrim (Chapter 33) – Kris Kristofferson
11. Sunday Mornin’ Comin’ Down – Johnny Cash
12. Casey’s Last Ride – Kris Kristofferson & Willie Nelson
13. Born and Raised in Black and White – The Highwaymen
14. The Devil’s Right Hand – The Highwaymen
15. There Ain’t No Good Chain Gang – Johnny Cash and Waylon Jennings
16. The Road Goes On Forever – The Highwaymen
17. I Wish I Was Crazy Again – Johnny Cash
18. Desperados Waiting for a Train – The Highwaymen
Disc 2
1. Good Hearted Woman – Waylon Jennings & Willie Nelson
2. A Backstage Pass – The Highwaymen
3. How Do You Feel About Foolin’ Around – Willie Nelson
4. Luckenbach, Texas (Back to the Basics of Love) – Waylon Jennings
5. The Night Hank Williams Came to Town – Johnny Cash
6. If You Don’t Like Hank Williams – Kris Kristofferson
7. Are You Sure Hank Done It This Way? – Waylon Jennings
8. Big River – The Highwaymen
9. Deportee (Plane Wreck at Los Gatos) – The Highwaymen
10. Me and Bobby McGee – Kris Kristofferson
11. The Last Cowboy Song – The Highwaymen
12. Mamas Don’t Let Your Babies Grow Up to Be Cowboys – Waylon Jennings & Willie Nelson
13. Even Cowgirls Get the Blues – Johnny Cash and Waylon Jennings
14. Nowhere Road – Waylon Jennings & Willie Nelson
15. It Is What It Is – The Highwaymen
16. Living Legend – The Highwaymen
17. Love Is the Way – Johnny Cash and Waylon Jennings
18. Live Forever – The Highwaymen