Nikolaj Coster-Waldau Jacob 'Money' Harlon Omari Hardwick Kutcher Jon Bernthal Frank 'Shotgun' Lake Bell Kate Harlon Emory Cohen Howie Jeffrey Donovan Bottles Holt McCallany Jerry 'The Beast' Manning Evan Jones Chopper Benjamin Bratt Sanchez Chris Browning Toby 'Redwood' Simms Max Greenfield Tom Jessy Schram Jennifer Juan Pablo Raba Herman Gomez Matt Gerald Phil Cole Michael Landes Steve Keith Jardine Ripper Sarah Minnich Janie Jonathon McClendon Joshua Harlon Derek Dinniene Young Joshua Harlon Monique Candelaria Lola Gomez Cru Ennis Jason Horvath Danny Winn Doyle David House Capt. Freeman Diego Joaquin Lopez Cellmate Lopez Bobby Lee Osborn Lenny Brendan Kelly Large Biker Dylan Kenin Trustee Matthew Page SHU Guard Mark Sivertsen LT. Roberts John Christian Love Young Black Inmate Chris Adams Inmate Esodie Geiger Judge Michael Sheets Lead Officer Mike Ostroski Banker-Type Nathaniel Augustson Chef J. Nathan Simmons Prison Inmate Howard Ferguson Jr. Basketball Opponent Joshua R. Aragon Inmate Jacob Browne AD Seg Guard Jetto Dorsainville Bailiff Marika Day Punk-Rocker Girl David Miller Prisoner Diana Gaitirira R&R Guard Joseph P. Santillanes Back-Up Police Officer Cajardo Lindsey Chino Guard Rodger Larance Pedestrian