Guest Stars Leon Rippy as Dr. Milton Beauregard Jeananne Goossen as Nikki Ben Cotton as Yapper Mahershala Ali as Clarence Montgomery Glynn Turman as Emmitt Little Co Starring Tim Perez as Police Chief Kimberly Sustad as Charlotte Christine Chatelain as Megan Palmer John Murphy as Frank James Bamford as White Inmate Marc Senior as Young Emmitt Little Barry Nerling as Mess Hall Guard Michael Bardach as ND Prisoner #2 Ryan Bruce as Young Republican Drummond Macdougall as Right Winger Sarah Blondin as Kate Aubrey Sixto as Barber Eric Fell as Club Manager Greig Thorlacius as ND Prisoner #1 Panos Bilalakis as Cell Guard