Guest Stars Vincent Pastore as Fat Larry Andrea-Rachel Parker as Mama Ganja Stephen McKinley Henderson as Uncle Hollis Kecia Lewis as Aunt Goldie Anthony Chisholm as Old Chess Player Jorge Lendeborg Jr. as Jah Son Ja'Quan Cole as B-Black Co Starring Ebony Obsidian as Nia Justus Davis Graham as Randy Diggs Amyrh Harris as Darren Coles Samuel McKoy-Johnson as Darius Coles Delissa Reynolds as Ann Coles Trayce Malachi as Young Bobby Nicholas Richardson as Stockbroker Lucas Papaelias as Salesman Joey Auzenne as Fredo Popa Wu as Five Percenter Hank Strong as Prisoner #2 Teniece Divya Johnson as Woman William Oliver Watkins as Bobby's Father CJ McBath as Dealer Rachel Lu as Asian Cashier Robbie Tate-Brickle as Man Myles Marable as Customer Will Ehren as Worker Dexton P. Cummings as Prisoner #1 Chris Jarell as Orin