1. Commentary: Herbie Hancock, Jimmy Heath
2. Milestones (1958)
3. Commentary: Greg Tate
4. Donna Lee (Charlie Parker with Miles Davis) (1947)
5. Commentary: Ashley Kahn, Symphony Sid Introduction
6. Moon Dreams (1949)
7. Commentary: George Wein
8. ‘Round Midnight (1957)
9. Commentary: Carlos Santana
10. It Never Entered My Mind (1959)
11. Commentary: Vincent Bessieres
12. Generique (1958)
13. Commentary: Jimmy Cobb
14. So What (1959)
15. Commentary: Gil Evans
16. New Rhumba (1957)
17. Commentary: Frances Taylor Davis
18. The Pan Piper (Alborada de Vigo) (1960)
19. Commentary: Jack Chambers
20. Someday My Prince Will Come (1961)
21. Commentary: Wayne Shorter
22. Footprints (1967)
23. Commentary: Carlos Santana, Quincy Troupe
24. Miles Runs The Voodoo Down (45RPM Single Edit) (1970)
25. Commentary: Marcus Miller
26. Tutu (1986)
27. Commentary: Erin Davis
28. Hail To The Real Chief (Brand New Recording featuring unreleased Miles Davis performances; Produced by Lenny White & Vince Wilburn, Jr.)