Lets Go to Prison (2006)

Bob Odenkirk's jail comedy Let's Go to Prison!, stars Will Arnett as Nelson Biederman IV, the son of a judge who ends up being sentenced to serve time in Rossmore State Penitentiary. During one of his rare stints out of incarceration, career criminal John Lyshitski (Dax Shepard) learns of the conviction. John holds a grudge against Nelson's father and decides to get his revenge by going back to jail and making Nelson's stay there as horrible as possible. Chi McBride co-stars as a fellow inmate.