Reg. E. Gains and Savion Glover -- "Pawn Shop"; Tommy Chunn -- "Computer Wordplay"; Scorpio Blues -- "Second Guessing"; Gemineye -- "Penny For Your Thoughts"; Emmanuel Xavier -- "Nueva York"; Mayda Del Valle -- "To All the Boys I've Loved Before"; Rev. Run -- "Peter Piper"; Aulelei Love -- "Same Cell, A poem for Women in Prison"; Mike Booker -- "Hoodology"; Smokey Robinson -- "Gang Bangin'"
| Name | Type | Role | |
|---|---|---|---|
| Rev. Run | Guest Star |