Let's Go to Prison (2006) on Netflix

John Lyshitski is a car stealing slacker, with a weed problem, and has been in Illinois' Rossmore State Penitentiary so many times, he knows its entire population of both staff and cons by their first names. Cursed with the old ill luck of being in the wrong place, at the wrong time, in possession of the wrong car, he's been deemed a lost cause repeat offender in the eyes of everyone else. When the heartless judge, who has been behind most of his sentences, goes to the big court house in the sky, John decides to ruin the man's legacy by having the judge's only offspring, Nelson Biederman IV, thrown in the slammer along with him. Here, the world-class selfish jerk learns a certain old lesson the hard way: Do unto others as you would have others do unto you. But has John gone too far in the payback department?