| Ernie Hudson | Warden Leo Glynn |
| Terry Kinney | Tim McManus |
| Rita Moreno | Sister Peter Marie Reimondo |
| Harold Perrineau | Augustus Hill |
| J.K. Simmons | Vern Schillinger |
| Lee Tergesen | Tobias Beecher |
| Eamonn Walker | Kareem Said |
| Dean Winters | Ryan O'Reily |
| Betty Buckley | Suzanne Fitzgerald |
| John Doman | Edward Galson |
| Rick Fox | Jackson Vahue |
| Zeljko Ivanek | Governor James Devlin |
| George Morfogen | Bob Rebadow |
| Brían F. O'Byrne | Padraic Connelly |
| Austin Pendleton | William Giles |
| Luke Perry | Reverend Jeremiah Cloutier |
| Luna Lauren Velez | Dr. Gloria Nathan
(as Lauren Vélez) |
| Scott William Winters | Cyril O'Reily |
| Michael Wright | Omar White |
| Granville Adams | Zahir Arif |
| Anthony Chisholm | Burr Redding |
| Robert Clohessy | Officer Sean Murphy |
| Seth Gilliam | Clayton Hughes |
| Lord Jamar | Kevin 'Supreme Allah' Ketchum |
| Tom Mardirosian | Agamemnon Busmalis |
| Method Man | Carlton 'Tug' Daniels |
| Kathryn Meisle | Mrs. Rockwell |
| Craig muMs Grant | Poet
(as muMs) |
| Sandra Purpuro | Katherine McClain |
| Kristin Rohde | Officer Claire Howell |
| David Zayas | Enrique Morales |
| Chuck Zito | Chucky Pancamo |
| Kirk Acevedo | Miguel Alvarez
(archive footage) |
| Jerome Preston Bates | Officer Travis Smith |
| Peter Hans Benson | Reporter
(as Peter Benson) |
| Timothy L. Brown | Officer Jason Armstrong |
| Sean Dugan | Timmy Kirk |
| Cyrus Farmer | Officer Adrian Johnson |
| Jon Korkes | Officer Tom Robinson |
| Jenna Lamia | Carrie Schillinger |
| Carlos Leon | Carlos Martinez |
| Tom Ligon | Alvin Yood |
| Larry Pine | Arnie Zelman |
| Blake Robbins | Officer Dave Brass |
| R.E. Rodgers | James Robson |
| Bert Rotundo | Prisoner |
| Otto Sanchez | Chico Guerra |
| Philip Scozzarella | Officer Joseph Mineo
(as Philip V. Scozzarella) |
| Thomas G. Waites | Harry Stanton |
| Alex Webb | Dave Rockwell |
| Bill Boggs | Self
(uncredited) |
| Frank Bonsangue | Sicilian Crew
(uncredited) |
| Ty Copeman | Corrections Officer
(uncredited) |
| Peter Dinklage | Murder Victim
(uncredited) |
| Gordon Elliott | Self
(uncredited) |
| Raymond Michael Karl | Officer #2
(uncredited) |
| Peter James Kelsch | Jim Burns
(uncredited) |
| Joan Bennett Kennedy | Self
(uncredited) |
| Seth William Meier | Liam Meaney
(uncredited) |