| Ernie Hudson | Warden Leo Glynn |
| Terry Kinney | Tim McManus |
| Harold Perrineau | Augustus Hill |
| Eamonn Walker | Kareem Said |
| Kirk Acevedo | Miguel Alvarez |
| Edie Falco | Officer Diane Whittlesey |
| Leon | Jefferson Keane /
Tizi Ouzou |
| Rita Moreno | Sister Peter Marie Reimondo |
| Tony Musante | Nino Schibetta |
| J.K. Simmons | Vern Schillinger |
| Lee Tergesen | Tobias Beecher |
| Sean Whitesell | Donald Groves |
| Dean Winters | Ryan O'Reily |
| BD Wong | Father Ray Mukada |
| Zeljko Ivanek | Governor James Devlin |
| Adewale Akinnuoye-Agbaje | Simon Adebisi |
| George Morfogen | Bob Rebadow |
| Skipp Sudduth | Lenny Burrano |
| Scott Cohen | Agent Jeremy Goldstein |
| O.L. Duke | Paul Markstram |
| Goodfella Mike G | Joey D'Angelo |
| Benny Nieves | Carlos Rodrigo |
| Steve Ryan | Officer Mike Healy |
| J.D. Williams | Kenny Wangler |
| Raul Aranas | Jorge Vargas |
| Elizabeth Rodriguez | Maritza Alvarez |
| Derrick Simmons | Billie Keane |
| Philip Scozzarella | Officer Joseph Mineo |
| Eugene Ashe | Singer |
| Paul Frazier | Singer |
| Ray Frazier | Singer |
| Frank Bonsangue | Sicilian Crew
(uncredited) |
| Eddie J. Fernandez | Martinez
(uncredited) |
| Josh Mowery | Prison Guard
(uncredited) |
| Manos Pantelidis | Inmate
(uncredited) |
| Leif Riddell | Mark Mack
(uncredited) |
| Jack Shamblin | Arian Brother
(uncredited) |