Guest Stars Syam M. Lafi as Hasan Khan Chris McKinney as Rikers Head CO Mustafa Shakir as Victor 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 Babs Olusanmokun as Marvin Jason Ralph as TBD Malachi Weir as TBD Paul Carafotes as Rose Aida Turturro as Rehab Worker Wallace Smith as Holding Cell Inmate Jennifer Onvie as Janine 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 Brian Tarantina as Bar Patron Roosevelt Davis as Holding Cell Guard Punchin' Pat Nwamu as Freddy's Boxing Opponent