Director Marc Levin travels to Chicago with hip-hop legend Chuck D (from Public Enemy) and Marshall Chess (son of Leonard Chess and heir to the legacy of Chess Records) to explore the heyday of the Chicago blues and how they come together to produce an album that seeks to bring veteran blues players along with contemporary hip hop musicians. Along with never before seen footage from Howlin 'Wolf, Muddy Waters and Paul Butterfield Blues Band, they are original performances by Koko Taylor, Otis Rush, Magic Slim, Ike Turner and Sam Lay.
| Actor | Role |
|---|---|
| MMarshall ChessSelf | Self |
 Bo DiddleySelf (archival) | Self (archival) |
 Paul ButterfieldSelf | Self |
 Chuck DSelf | Self |
 Mick JaggerSelf | Self |
 CommonSelf | Self |
| WWillie DixonSelf (archival) | Self (archival) |
 Public EnemySelf (archival) | Self (archival) |
 Ike TurnerSelf | Self |
 Muddy WatersSelf | Self |
| SSonny Boy Williamson IISelf | Self |
 Howlin' WolfSelf | Self |