Disc 1

1. I Ain't Living Long Like This  - Rodney Crowell  - Chris Stapleton  - Morgane Stapleton
2. Whistlers and Jugglers  - Jesse Dayton  - Shooter Jennings  - Shel Silverstein
3. Mona  - Jessi Colter  - Mirriam Eddy
4. Only Daddy That'll Walk the Line  - Bobby Bare  - Ivy J. Bryant
5. Ride Me Down Easy  - Billy Joe Shaver  - Lee Ann Womack
6. Yours Love  - Harlan Howard  - Buddy Miller  - Lee Ann Womack
7. Freedom to Stay  - Bill Hoover  - Jamey Johnson
8. The Wurlitzer Prize  - Bobby Emmons  - Chips Moman  - Kacey Musgraves
9. Are You Sure Hank Done It This Way  - Waylon Jennings  - Robert Earl Keen
10. I Do Believe  - Waylon Jennings  - Kris Kristofferson
11. Rainy Day Woman  - Ryan Bingham  - Waylon Jennings
12. Dreaming My Dreams With You  - Alison Krauss  - Allen Reynolds
13. I Ain't the One  - Jessi Colter  - Mirriam Eddy  - Jamey Johnson  - Alison Krauss
14. Honky Tonk Heroes  - Toby Keith  - Billy Joe Shaver
15. Lonesome, On'ry and Mean  - Eric Church  - Stephen Young
16. Till I Gain Control Again  - Rodney Crowell  - Willie Nelson
17. Mammas Don't Let Your Babies Grow Up to Be Cowboys  - Patsy Bruce  - Toby Keith  - Willie Nelson
18. My Heroes Have Always Been Cowboys  - Willie Nelson  - Chris Stapleton  - Sharon Vaughn
19. Highwayman  - Shooter Jennings  - Jamey Johnson  - Kris Kristofferson  - Willie Nelson  - Jimmy Webb
20. Luckenbach, Texas (Back to the Basics of Love)  - Bobby Emmons  -  Full Ensemble  - Chips Moman  - Willie Nelson

Disc 2

21. I Ain't Living Long Like This  - Chris Stapleton
22. Whistlers and Jugglers  - Shooter Jennings
23. Luckenbach, Texas (Back to the Basics of Love)  -  Full Ensemble  - Willie Nelson
24. Credits
25. Mona  - Jessi Colter
26. Only Daddy That'll Walk the Line  - Bobby Bare
27. Ride Me Down Easy  - Lee Ann Womack
28. Yours Love  - Buddy Miller  - Lee Ann Womack
29. Memories of You and I  - Sturgill Simpson
30. The Wurlitzer Prize  - Kacey Musgraves
31. Freedom to Stay  - Jamey Johnson
32. Are You Sure Hank Done It This Way  - Robert Earl Keen
33. I Do Believe  - Kris Kristofferson
34. Rainy Day Woman  - Ryan Bingham
35. Dreaming My Dreams With You  - Alison Krauss
36. I Ain't the One  - Jamey Johnson  - Alison Krauss
37. Honky Tonk Heroes  - Toby Keith
38. Lonesome, On'ry and Mean  - Eric Church
39. Till I Gain Control Again  - Willie Nelson
40. Mammas Don't Let Your Babies Grow Up to Be Cowboys  - Toby Keith  - Willie Nelson
41. My Heroes Have Always Been Cowboys  - Willie Nelson  - Chris Stapleton
42. I Can Get Off on You  - Willie Nelson  - Sturgill Simpson
43. Highwayman  - Shooter Jennings  - Jamey Johnson  - Kris Kristofferson  - Willie Nelson
44. Blackbird Opening Titles
45. Waylon Jennings Opening Titles
46. I Ain't Living Long Like This  - Chris Stapleton
47. Whistlers and Jugglers  - Shooter Jennings
48. Mona  - Jessi Colter
49. Only Daddy That'll Walk the Line  - Bobby Bare
50. Ride Me Down Easy  - Lee Ann Womack
51. Yours Love  - Buddy Miller  - Lee Ann Womack
52. Freedom to Stay  - Jamey Johnson
53. The Wurlitzer Prize  - Kacey Musgraves
54. Are You Sure Hank Done It This Way  - Robert Earl Keen
55. I Do Believe  - Kris Kristofferson
56. Rainy Day Woman  - Ryan Bingham
57. Dreaming My Dreams With You  - Alison Krauss
58. I Ain't the One  - Jamey Johnson  - Alison Krauss
59. Honky Tonk Heroes  - Toby Keith
60. Lonesome, On'ry and Mean  - Eric Church
61. Till I Gain Control Again  - Willie Nelson
62. Mammas Don't Let Your Babies Grow Up to Be Cowboys  - Toby Keith  - Willie Nelson
63. My Heroes Have Always Been Cowboys  - Willie Nelson  - Chris Stapleton
64. I Can Get Off on You  - Willie Nelson  - Sturgill Simpson
65. Highwayman  - Shooter Jennings  - Jamey Johnson  - Kris Kristofferson  - Willie Nelson
66. Luckenbach, Texas (Back to the Basics of Love)  -  Full Ensemble  - Willie Nelson
67. Credits
68. Waylon in a Word
69. Waylon's Influence
70. The Highwaymen
71. First Heard Waylon
72. Gone Fishin'
73. Highwaymen Family
74. Outlaws