Prison comedy in which a serial con is banged up with the son of the judge who put him indoors. John Lyshitski (Dax Shepherd) is a helpless career con. He's not even good at it - in fact he gets caught so often he's on first name terms with the entire staff at Rossmore State Pen in fact. One judge, Biederman, has been behind most of his sentences over the years so there's naturally an ill-will between them. Judge Biederman finally kicks the can and Lyshitski decides that the next time he's going away, he's taking Biederman Junior with him.