This revealing portrait of comedian, activist, pop-culture icon and thought leader Dick Gregory documents his many personal reinventions throughout the decades, from celebrity to civil rights hero and beyond, while hearing from the incredible entertainers who have been inspired by his blueprint.
| Actor | Role |
|---|---|
 Dick GregorySelf | Self |
 Chris RockSelf | Self |
 Harry BelafonteSelf | Self |
 Kevin HartSelf | Self |
 Lena WaitheSelf | Self |
 Dave ChappelleSelf | Self |
 Wanda SykesSelf | Self |
 Nick CannonSelf | Self |
 Rob SchneiderSelf | Self |
 W. Kamau BellSelf | Self |
 Lawrence O'DonnellSelf | Self |
| LLillian GregorySelf | Self |
| SSteve JaffeSelf | Self |
| RRock NewmanSelf | Self |
 Robert LipsyteSelf | Self |
| CChristian GregorySelf | Self |
| AAyanna GregorySelf | Self |
| YYohance GregorySelf | Self |
| CCathy HughesSelf | Self |
 Ed BradleySelf (archive footage) | Self (archive footage) |