Guest Stars Delaney Williams as Sgt. Jay Landsman Robert F. Chew as Joseph "Proposition Joe" Stewart Michael Kostroff as Maurice "Maury" Levy Jermaine Crawford as Duquan "Dukie" Weems Maestro Harrell as Randy Wagstaff Dan Deluca as UM Professor David Parenti Julito McCullum as Namond Brice Jeffrey Lorenzo as Karim Williams Shamika Cotton as Michael's Mother Dion Graham as Rupert Bond Edward Green as Spider Nathan Corbett as Donut Susan Duvall as Assistant Principal Marcia Donnelly Stacie Davis as Ms. Duquette Jonnie Brown as Officer Eddie Walker Susan Rome as State's Attorney Ilene Nathan Rashad Orange as Sherrod Melvin T. Russell as Jamal Ed Norris as Detective Edward Norris Sam Coppola as Former Mayor Tony Melissa D. Madison as Lieutenant Grayson Greg Ainsworth as Richard Switowski