Kirk Acevedo Miguel Alvarez Actor Adewale Akinnuoye-Agbaje Simon Adebisi 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 Edie Falco Officer Diane Whittlesey Guest Star Luis Guzmán Raoul 'El Cid' Hernandez Guest Star Olek Krupa Yuri Kosygin 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 Frederick Koehler Andrew Schillinger Guest Star Scott William Winters Cyril O'Reily Guest Star Ernie Hudson Jr. Khan Guest Star Barry Levinson Executive Producer Tom Fontana Executive Producer, Writer Bradford Winters Writer Steve Buscemi Director