Kirk Acevedo Miguel Alvarez Actor Ernie Hudson Warden Leo Glynn Actor Terry Kinney Tim McManus Actor Rita Moreno Sister Peter Marie Reimondo Actor Harold Perrineau Augustus Hill Actor J.K. Simmons Vern Schillinger Actor Lee Tergesen Tobias "Toby" Beecher Actor Eamonn Walker Kareem Said Actor Dean Winters Ryan O'Reily Actor Adewale Akinnuoye-Agbaje Simon Adebisi Guest Star George Morfogen Bob Rebadow Guest Star Luna Lauren Velez Dr. Gloria Nathan Guest Star Edie Falco Officer Diane Whittlesey Guest Star BD Wong Father Ray Mukada Guest Star Austin Pendleton William Giles Guest Star LL Cool J Jiggy Walker Guest Star Eddie Malavarca Peter Schibetta Guest Star Luis Guzmán Raoul 'El Cid' Hernandez Guest Star Barry Levinson Executive Producer Tom Fontana Executive Producer, Writer Alan Taylor Director