Guest Stars Leon Rippy as Dr. Milton Beauregard Jeananne Goossen as Nikki Ben Cotton as Yapper Glynn Turman as Emmitt Little Mahershala Ali as Clarence Montgomery Co Starring Tim Perez as Police Chief Kimberly Sustad as Charlotte Christine Chatelain as Megan Palmer Marc Senior as Young Emmitt Little Barry Nerling as Mess Hall Guard James Bamford as White Inmate Michael Bardach as ND Prisoner #2 John Murphy as Frank 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