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 Adam LeFevre as Judge Albert Jones as District Attorney Jack Gilpin as Doctor Cliff Moylan as Arraignment Bailiff Racquel Bailey as Ciara Babs Olusanmokun as Marvin Jason Ralph as TBD Max Casella as Edgar Aida Turturro as Rehab Worker Wallace Smith as Holding Cell Inmate Paul Carafotes as Rose Malachi Weir as TBD Mellini Kantayya as Principal Erik McKay as DeVaughn Daniel J. Watts as Holding Cell Inmate Will Cobbs as Holding Cell Inmate Damien Lemon as Defendant Jennifer Onvie as Janine Brian Tarantina as Bar Patron Roosevelt Davis as Holding Cell Guard Punchin' Pat Nwamu as Freddy's Boxing Opponent