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 Cliff Moylan as Arraignment Bailiff Jack Gilpin as Doctor Adam LeFevre as Judge Racquel Bailey as Ciara Max Casella as Edgar Jason Ralph as TBD Babs Olusanmokun as Marvin Paul Carafotes as Rose Malachi Weir as TBD Wallace Smith as Holding Cell Inmate Aida Turturro as Rehab Worker Roosevelt Davis as Holding Cell Guard 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 Punchin' Pat Nwamu as Freddy's Boxing Opponent