Disc 1
- I Ain't Living Long Like This - Rodney Crowell - Chris Stapleton - Morgane Stapleton
- Whistlers and Jugglers - Jesse Dayton - Shooter Jennings - Shel Silverstein
- Mona - Jessi Colter - Mirriam Eddy
- Only Daddy That'll Walk the Line - Bobby Bare - Ivy J. Bryant
- Ride Me Down Easy - Billy Joe Shaver - Lee Ann Womack
- Yours Love - Harlan Howard - Buddy Miller - Lee Ann Womack
- Freedom to Stay - Bill Hoover - Jamey Johnson
- The Wurlitzer Prize - Bobby Emmons - Chips Moman - Kacey Musgraves
- Are You Sure Hank Done It This Way - Waylon Jennings - Robert Earl Keen
- I Do Believe - Waylon Jennings - Kris Kristofferson
- Rainy Day Woman - Ryan Bingham - Waylon Jennings
- Dreaming My Dreams With You - Alison Krauss - Allen Reynolds
- I Ain't the One - Jessi Colter - Mirriam Eddy - Jamey Johnson - Alison Krauss
- Honky Tonk Heroes - Toby Keith - Billy Joe Shaver
- Lonesome, On'ry and Mean - Eric Church - Stephen Young
- Till I Gain Control Again - Rodney Crowell - Willie Nelson
- Mammas Don't Let Your Babies Grow Up to Be Cowboys - Patsy Bruce - Toby Keith - Willie Nelson
- My Heroes Have Always Been Cowboys - Willie Nelson - Chris Stapleton - Sharon Vaughn
- Highwayman - Shooter Jennings - Jamey Johnson - Kris Kristofferson - Willie Nelson - Jimmy Webb
- Luckenbach, Texas (Back to the Basics of Love) - Bobby Emmons - Full Ensemble - Chips Moman - Willie Nelson
Disc 2
- I Ain't Living Long Like This - Chris Stapleton
- Whistlers and Jugglers - Shooter Jennings
- Luckenbach, Texas (Back to the Basics of Love) - Full Ensemble - Willie Nelson
- Credits
- Mona - Jessi Colter
- Only Daddy That'll Walk the Line - Bobby Bare
- Ride Me Down Easy - Lee Ann Womack
- Yours Love - Buddy Miller - Lee Ann Womack
- Memories of You and I - Sturgill Simpson
- The Wurlitzer Prize - Kacey Musgraves
- Freedom to Stay - Jamey Johnson
- Are You Sure Hank Done It This Way - Robert Earl Keen
- I Do Believe - Kris Kristofferson
- Rainy Day Woman - Ryan Bingham
- Dreaming My Dreams With You - Alison Krauss
- I Ain't the One - Jamey Johnson - Alison Krauss
- Honky Tonk Heroes - Toby Keith
- Lonesome, On'ry and Mean - Eric Church
- Till I Gain Control Again - Willie Nelson
- Mammas Don't Let Your Babies Grow Up to Be Cowboys - Toby Keith - Willie Nelson
- My Heroes Have Always Been Cowboys - Willie Nelson - Chris Stapleton
- I Can Get Off on You - Willie Nelson - Sturgill Simpson
- Highwayman - Shooter Jennings - Jamey Johnson - Kris Kristofferson - Willie Nelson
- Blackbird Opening Titles
- Waylon Jennings Opening Titles
- I Ain't Living Long Like This - Chris Stapleton
- Whistlers and Jugglers - Shooter Jennings
- Mona - Jessi Colter
- Only Daddy That'll Walk the Line - Bobby Bare
- Ride Me Down Easy - Lee Ann Womack
- Yours Love - Buddy Miller - Lee Ann Womack
- Freedom to Stay - Jamey Johnson
- The Wurlitzer Prize - Kacey Musgraves
- Are You Sure Hank Done It This Way - Robert Earl Keen
- I Do Believe - Kris Kristofferson
- Rainy Day Woman - Ryan Bingham
- Dreaming My Dreams With You - Alison Krauss
- I Ain't the One - Jamey Johnson - Alison Krauss
- Honky Tonk Heroes - Toby Keith
- Lonesome, On'ry and Mean - Eric Church
- Till I Gain Control Again - Willie Nelson
- Mammas Don't Let Your Babies Grow Up to Be Cowboys - Toby Keith - Willie Nelson
- My Heroes Have Always Been Cowboys - Willie Nelson - Chris Stapleton
- I Can Get Off on You - Willie Nelson - Sturgill Simpson
- Highwayman - Shooter Jennings - Jamey Johnson - Kris Kristofferson - Willie Nelson
- Luckenbach, Texas (Back to the Basics of Love) - Full Ensemble - Willie Nelson
- Credits
- Waylon in a Word
- Waylon's Influence
- The Highwaymen
- First Heard Waylon
- Gone Fishin'
- Highwaymen Family
- Outlaws