| 1 | Commentary: Herbie Hancock, Jimmy Heath | Herbie Hancock, Jimmy Heath | 0:22 |
| 2 | Milestones | Miles Davis | 5:42 |
| 3 | Commentary: Greg Tate | Greg Tate | 0:19 |
| 4 | Donna Lee | Charlie Parker with Miles Davis | 2:32 |
| 5 | Commentary: Ashley Kahn, Symphony Sid Introduction | Ashley Kahn, Symphony Sid Torin | 0:37 |
| 6 | Moon Dreams | Miles Davis | 3:16 |
| 7 | Commentary: George Wein | George Wein | 0:28 |
| 8 | 'Round Midnight | Miles Davis | 5:55 |
| 9 | Commentary: Carlos Santana | Carlos Santana | 0:20 |
| 10 | It Never Entered My Mind | Miles Davis Quintet | 5:22 |
| 11 | Commentary: Vincent Bessieres | Vincent Bessières | 0:44 |
| 12 | Générique (Mono Version) | Miles Davis | 2:47 |
| 13 | Commentary: Jimmy Cobb | Jimmy Cobb | 0:21 |
| 14 | So What | Miles Davis | 9:05 |
| 15 | Commentary: Gil Evans | Gil Evans | 0:11 |
| 16 | New Rhumba | Miles Davis | 4:35 |
| 17 | Commentary: Frances Taylor Davis | Frances Taylor Davis | 0:37 |
| 18 | The Pan Piper | Miles Davis | 3:55 |
| 19 | Commentary: Jack Chambers | Jack Chambers | 0:22 |
| 20 | Someday My Prince Will Come | Miles Davis | 9:02 |
| 21 | Commentary: Wayne Shorter | Wayne Shorter | 0:34 |
| 22 | Footprints | Miles Davis | 9:45 |
| 23 | Commentary: Carlos Santana, Quincy Troupe | Carlos Santana, Quincy Troupe | 0:27 |
| 24 | Miles Runs the Voodoo Down (45-rpm Single Edit) | Miles Davis | 2:49 |
| 25 | Commentary: Marcus Miller | Marcus Miller | 0:17 |
| 26 | Tutu | Miles Davis | 5:14 |
| 27 | Commentary: Erin Davis | Erin Davis | 0:13 |
| 28 | Hail To the Real Chief | Miles Davis | 3:40 |