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| Dax Shepard | John Lyshitski |
| Will Arnett | Nelson Biederman IV |
| Chi McBride | Barry |
| Dylan Baker | Warden |
| David Koechner | Shanahan |
| Michael Shannon | Lynard |
| Miguel Nino | Jesus |
| Jay Whittaker | Icepick |
| Amy Hill | Judge Eva Fwae Wun |
| David Darlow | Judge Biederman |
| Joseph Marcus | Pawn Broker |
| Jerry Minor | Breen Guard |
| Nick Phalen | John (8 Years) |
| A.J. Balance | John (18 Years) |
| Bob Odenkirk | Duane |
Career criminal John Lyshitski wants revenge on the now-dead judge who put him away. He gets a prime opportunity when the judge's son, though innocent of a crime, is convicted and sent to jail. John immediately has himself thrown back in the clink to become Nelson's cellmate and make sure he gets the full prison experience.
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