Kirk Acevedo Miguel Alvarez Actor Adewale Akinnuoye-Agbaje Simon Adebisi Actor Ernie Hudson Warden Leo Glynn Actor Terry Kinney Tim McManus Actor, Director 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 Kathryn Erbe Shirley Bellinger Guest Star Edie Falco Officer Diane Whittlesey Guest Star Luis Guzmán Raoul 'El Cid' Hernandez Guest Star Mark Margolis Antonio Nappa Guest Star Christopher Meloni Chris Keller Guest Star Luna Lauren Velez Dr. Gloria Nathan Guest Star BD Wong Father Ray Mukada Guest Star Philip Casnoff Nikolai Stanislofsky Guest Star Scott William Winters Cyril O'Reily Guest Star Ernie Hudson Jr. Hamid Khan Guest Star Barry Levinson Executive Producer Tom Fontana Executive Producer, Writer Nick Gomez Director Bradford Winters Writer Matt Dillon Director Sunil Nayar Writer Keith Samples Director Steve Buscemi Director Adam Bernstein Director Chazz Palminteri Director