Ernie Hudson Ernie Hudson ... Warden Leo Glynn 56 episodes, 1997-2003
J.K. Simmons J.K. Simmons ... Vern Schillinger 56 episodes, 1997-2003
Lee Tergesen Lee Tergesen ... Tobias Beecher 56 episodes, 1997-2003
Dean Winters Dean Winters ... Ryan O'Reily 56 episodes, 1997-2003
George Morfogen George Morfogen ... Bob Rebadow 56 episodes, 1997-2003
Terry Kinney Terry Kinney ... Tim McManus 55 episodes, 1997-2003
Rita Moreno Rita Moreno ... Sister Peter Marie Reimondo 55 episodes, 1997-2003
Harold Perrineau Harold Perrineau ... Augustus Hill 55 episodes, 1997-2003
Eamonn Walker Eamonn Walker ... Kareem Said 51 episodes, 1997-2003
Craig muMs Grant Craig muMs Grant ... Poet 49 episodes, 1997-2003
Luna Lauren Velez Luna Lauren Velez ... Dr. Gloria Nathan 48 episodes, 1997-2003
Granville Adams Granville Adams ... Zahir Arif 48 episodes, 1997-2003
Tom Mardirosian Tom Mardirosian ... Agamemnon Busmalis 47 episodes, 1998-2003
Kirk Acevedo Kirk Acevedo ... Miguel Alvarez 48 episodes, 1997-2003
BD Wong BD Wong ... Father Ray Mukada 46 episodes, 1997-2003
Chuck Zito Chuck Zito ... Chucky Pancamo 46 episodes, 1998-2003
Philip Scozzarella Philip Scozzarella ... Officer Joseph Mineo / ... 46 episodes, 1997-2003
Scott William Winters Scott William Winters ... Cyril O'Reily 45 episodes, 1998-2003
Otto Sanchez Otto Sanchez ... Chico Guerra 40 episodes, 1998-2003
Christopher Meloni Christopher Meloni ... Chris Keller 38 episodes, 1998-2003
Robert Clohessy Robert Clohessy ... Officer Sean Murphy 38 episodes, 1999-2003
R.E. Rodgers R.E. Rodgers ... James Robson 36 episodes, 1998-2003
Kristin Rohde Kristin Rohde ... Officer Claire Howell 35 episodes, 1999-2003
Carl DiMaggio Carl DiMaggio ... Officer Len Lopresti / ... 34 episodes, 1999-2003
Evan Seinfeld Evan Seinfeld ... Jaz Hoyt 33 episodes, 1998-2003
Adewale Akinnuoye-Agbaje Adewale Akinnuoye-Agbaje ... Simon Adebisi 32 episodes, 1997-2000
Timothy L. Brown Timothy L. Brown ... Officer Jason Armstrong 32 episodes, 1997-2003
Zeljko Ivanek Zeljko Ivanek ... Governor James Devlin 27 episodes, 1997-2003
Steven Wishnoff Steven Wishnoff ... Tony Masters 27 episodes, 1999-2003
David Zayas David Zayas ... Enrique Morales 26 episodes, 2000-2003
Sean Dugan Sean Dugan ... Timmy Kirk 26 episodes, 1998-2003
Anthony Chisholm Anthony Chisholm ... Burr Redding 23 episodes, 2001-2003
Edie Falco Edie Falco ... Officer Diane Whittlesey 23 episodes, 1997-2000
J.D. Williams J.D. Williams ... Kenny Wangler / ... 23 episodes, 1997-2000
Michael Wright Michael Wright ... Omar White 22 episodes, 2001-2003
Todd Etelson Todd Etelson ... Mario Seggio
J.K. Simmons J.K. Simmons ... Vern Schillinger 56 episodes, 1997-2003
Lee Tergesen Lee Tergesen ... Tobias Beecher 56 episodes, 1997-2003
Dean Winters Dean Winters ... Ryan O'Reily 56 episodes, 1997-2003
George Morfogen George Morfogen ... Bob Rebadow 56 episodes, 1997-2003
Terry Kinney Terry Kinney ... Tim McManus 55 episodes, 1997-2003
Rita Moreno Rita Moreno ... Sister Peter Marie Reimondo 55 episodes, 1997-2003
Harold Perrineau Harold Perrineau ... Augustus Hill 55 episodes, 1997-2003
Eamonn Walker Eamonn Walker ... Kareem Said 51 episodes, 1997-2003
Craig muMs Grant Craig muMs Grant ... Poet 49 episodes, 1997-2003
Luna Lauren Velez Luna Lauren Velez ... Dr. Gloria Nathan 48 episodes, 1997-2003
Granville Adams Granville Adams ... Zahir Arif 48 episodes, 1997-2003
Tom Mardirosian Tom Mardirosian ... Agamemnon Busmalis 47 episodes, 1998-2003
Kirk Acevedo Kirk Acevedo ... Miguel Alvarez 48 episodes, 1997-2003
BD Wong BD Wong ... Father Ray Mukada 46 episodes, 1997-2003
Chuck Zito Chuck Zito ... Chucky Pancamo 46 episodes, 1998-2003
Philip Scozzarella Philip Scozzarella ... Officer Joseph Mineo / ... 46 episodes, 1997-2003
Scott William Winters Scott William Winters ... Cyril O'Reily 45 episodes, 1998-2003
Otto Sanchez Otto Sanchez ... Chico Guerra 40 episodes, 1998-2003
Christopher Meloni Christopher Meloni ... Chris Keller 38 episodes, 1998-2003
Robert Clohessy Robert Clohessy ... Officer Sean Murphy 38 episodes, 1999-2003
R.E. Rodgers R.E. Rodgers ... James Robson 36 episodes, 1998-2003
Kristin Rohde Kristin Rohde ... Officer Claire Howell 35 episodes, 1999-2003
Carl DiMaggio Carl DiMaggio ... Officer Len Lopresti / ... 34 episodes, 1999-2003
Evan Seinfeld Evan Seinfeld ... Jaz Hoyt 33 episodes, 1998-2003
Adewale Akinnuoye-Agbaje Adewale Akinnuoye-Agbaje ... Simon Adebisi 32 episodes, 1997-2000
Timothy L. Brown Timothy L. Brown ... Officer Jason Armstrong 32 episodes, 1997-2003
Zeljko Ivanek Zeljko Ivanek ... Governor James Devlin 27 episodes, 1997-2003
Steven Wishnoff Steven Wishnoff ... Tony Masters 27 episodes, 1999-2003
David Zayas David Zayas ... Enrique Morales 26 episodes, 2000-2003
Sean Dugan Sean Dugan ... Timmy Kirk 26 episodes, 1998-2003
Anthony Chisholm Anthony Chisholm ... Burr Redding 23 episodes, 2001-2003
Edie Falco Edie Falco ... Officer Diane Whittlesey 23 episodes, 1997-2000
J.D. Williams J.D. Williams ... Kenny Wangler / ... 23 episodes, 1997-2000
Michael Wright Michael Wright ... Omar White 22 episodes, 2001-2003
Todd Etelson Todd Etelson ... Mario Seggio