 Carl LumblyMiles Davis (voice) | Miles Davis (voice) |
| RReginald PettySelf - East St. Louis Resident | Self - East St. Louis Resident |
| QQuincy TroupeSelf - Writer | Self - Writer |
| FFarah GriffinSelf - Writer | Self - Writer |
| LLee Annie BonnerSelf - Childhood Friend | Self - Childhood Friend |
| AAshley KahnSelf - Writer | Self - Writer |
| BBenjamin CawthraSelf - Historian | Self - Historian |
 Jimmy HeathSelf - Musician | Self - Musician |
| JJimmy CobbSelf - Musician | Self - Musician |
| DDan MorgensternSelf - Writer | Self - Writer |
| GGreg TateSelf - Writer | Self - Writer |
 Gerald EarlySelf - Writer | Self - Writer |
 Quincy JonesSelf - Musician | Self - Musician |
 Wayne ShorterSelf - Musician | Self - Musician |
| TTammy L. KernodleSelf - Musicologist | Self - Musicologist |
 Juliette GrécoSelf - Singer | Self - Singer |
| VVincent BessièresSelf - Writer | Self - Writer |
| GGeorge WeinSelf - Jazz Promoter | Self - Jazz Promoter |
| EEugene RedmondSelf - East St. Louis Resident | Self - East St. Louis Resident |
 Carlos SantanaSelf - Musician | Self - Musician |
 Herbie HancockSelf - Musician | Self - Musician |
 Marcus MillerSelf - Musician | Self - Musician |
| CCortez McCoySelf - Friend | Self - Friend |
| SSandra McCoySelf - Friend | Self - Friend |
| JJack ChambersSelf - Historian | Self - Historian |
 Frances DavisSelf - Dancer / 1st Wife | Self - Dancer / 1st Wife |
| RRené UrtregerSelf - Musician | Self - Musician |
 Joshua RedmanSelf - Musician | Self - Musician |
 James MtumeSelf - Musician | Self - Musician |
 Lenny WhiteSelf - Musician | Self - Musician |
