Guest Stars Syam M. Lafi as Hasan Khan Mustafa Shakir as Victor Chris McKinney as Rikers Head CO Lord Jamar as Tino Fisher Stevens as Saul the Pharmacist Albert Jones as District Attorney Adam LeFevre as Judge Jack Gilpin as Doctor Cliff Moylan as Arraignment Bailiff Racquel Bailey as Ciara Max Casella as Edgar Jason Ralph as TBD Daniel J. Watts as Holding Cell Inmate Aida Turturro as Rehab Worker Babs Olusanmokun as Marvin Malachi Weir as TBD Wallace Smith as Holding Cell Inmate Paul Carafotes as Rose Roosevelt Davis as Holding Cell Guard Jennifer Onvie as Janine Erik McKay as DeVaughn Mellini Kantayya as Principal Will Cobbs as Holding Cell Inmate Damien Lemon as Defendant Brian Tarantina as Bar Patron Punchin' Pat Nwamu as Freddy's Boxing Opponent