Ernie Hudson Warden Leo Glynn Actor Terry Kinney Tim McManus Actor Harold Perrineau Augustus Hill Actor Eamonn Walker Kareem Said Actor Kirk Acevedo Miguel Alvarez Guest Star Edie Falco Officer Diane Whittlesey Guest Star Leon Jefferson Keane Guest Star Rita Moreno Sister Peter Marie Reimondo Guest Star Tony Musante Nino Schibetta Guest Star J.K. Simmons Vern Schillinger Guest Star Lee Tergesen Tobias "Toby" Beecher Guest Star Sean Whitesell Donald Groves Guest Star Dean Winters Ryan O'Reily Guest Star Luna Lauren Velez Dr. Gloria Nathan Guest Star Jon Seda Dino Ortolani Guest Star Darnell Martin Director Barry Levinson Executive Producer Tom Fontana Executive Producer