Carl Lumbly as Miles Davis (voice)

Reginald Petty as Self - East St. Louis Resident

Quincy Troupe as Self - Writer

Farah Griffin as Self - Writer

Lee Annie Bonner as Self - Childhood Friend

Ashley Kahn as Self - Writer

Benjamin Cawthra as Self - Historian

Jimmy Heath as Self - Musician

Jimmy Cobb as Self - Musician

Dan Morgenstern as Self - Writer

Greg Tate as Self - Writer

Gerald Early as Self - Writer

Quincy Jones as Self - Musician

Wayne Shorter as Self - Musician

Tammy L. Kernodle as Self - Musicologist

Juliette Gréco as Self - Singer

Vincent Bessières as Self - Writer

George Wein as Self - Jazz Promoter

Eugene Redmond as Self - East St. Louis Resident

Carlos Santana as Self - Musician

Herbie Hancock as Self - Musician

Marcus Miller as Self - Musician

Cortez McCoy as Self - Friend

Sandra McCoy as Self - Friend

Jack Chambers as Self - Historian

Frances Davis as Self - Dancer / 1st Wife

René Urtreger as Self - Musician

Joshua Redman as Self - Musician

James Mtume as Self - Musician

Lenny White as Self - Musician

Vince Wilburn Jr. as Self - Nephew

Archie Shepp as Self - Musician

Stanley Crouch as Self - Writer

Cheryl Davis as Self - Daughter

Ron Carter as Self - Musician

Clive Davis as Self - Columbia Records President

Marguerite Cantú as Self - Friend

Erin Davis as Self - Son

Mark Rothbaum as Self - Music Manager

Mike Stern as Self - Musician

Mikel Elam as Self - Personal Assistant

Jo Gelbard as Self - Painter

Wallace Roney as Self - Musician

Miles Davis as Self - Musician (archive footage)

Walter Cronkite as Self - Anchorman (archive footage)

Charlie Parker as Self - Musician (archive footage)

Dizzy Gillespie as Self - Musician (archive footage)

Thelonious Monk as Self - Musician (archive footage)

Johnny Mathis as Self - Singer (archive footage)

Louis Malle as Self - Filmmaker (archive footage)

Jeanne Moreau as Self - Actress (archive footage)

John Coltrane as Self - Musician (archive footage)

Gil Evans as Self - Music Arranger (archive footage)

Tony Williams as Self - Musician (archive footage)

Betty Davis as Self - Singer / 2nd Wife (archive footage)

Prince as Self - Musician (archive footage)