| Ernie Hudson | Warden Leo Glynn |
| 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 |
| Kevin Conway | Seamus O'Reilly |
| John Doman | Edward Galson |
| Rick Fox | Jackson Vahue |
| George Morfogen | Bob Rebadow |
| Austin Pendleton | William Giles |
| Luke Perry | Reverend Jeremiah Cloutier |
| Luna Lauren Velez | Dr. Gloria Nathan
(as Lauren Vélez) |
| Scott William Winters | Cyril O'Reily |
| BD Wong | Father Ray Mukada |
| 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 |
| Erik King | Moses Deyell |
| Tom Mardirosian | Agamemnon Busmalis |
| Method Man | Carlton 'Tug' Daniels |
| Craig muMs Grant | Poet
(as muMs) |
| Sandra Purpuro | Katherine McClain |
| Lance Reddick | John Basil |
| Kristin Rohde | Officer Claire Howell |
| Jacques C. Smith | Leroy Tidd /
Salah Yudin
(as Jacques Smith) |
| David Zayas | Enrique Morales |
| Chuck Zito | Chucky Pancamo |
| Greg Ainsworth | Weatherman |
| Dena Atlantic | Floria Mills |
| Jerome Preston Bates | Officer Travis Smith |
| Peter Hans Benson | Reporter
(as Peter Benson) |
| Timothy L. Brown | Officer Jason Armstrong |
| Angela Bullock | Dawn |
| Carl DiMaggio | Officer Len Lopresti |
| Sean Dugan | Timmy Kirk |
| Cyrus Farmer | Officer Adrian Johnson |
| M.G. Gong | Jia Kenmin
(as Michael Gregory Gong) |
| Elain R. Graham | Lenore Hughes
(as Elain Graham) |
| Joshua Harto | Carl Jenkins |
| Edward James Hyland | Jeffrey Seitz
(as Ed Hyland) |
| Jenna Lamia | Carrie Schillinger |
| Tom Ligon | Alvin Yood |
| Melissa Maxwell | Reporter #3 |
| Blayne Perry | Samuel Gougeon |
| R.E. Rodgers | James Robson |
| Otto Sanchez | Chico Guerra |
| Philip Scozzarella | Officer Joseph Mineo |
| Evan Seinfeld | Jaz Hoyt |
| Frank Bonsangue | Sicilian Crew
(uncredited) |
| John Carpenter | Self
(uncredited) |
| Jimmy DellaValle | Prisoner
(uncredited) |
| Brian Donahue | Correction Officer
(uncredited) |
| Gordon Elliott | Self
(uncredited) |
| Jim Lavin | Corrections Officer
(uncredited) |
| Grant Shaud | Self
(uncredited) |
| Steven Wishnoff | Tony Masters
(uncredited) |