Earl (Jason Lee) begins his jail sentence and discovers that life is not easy behind bars. He persistently tries to find out the best approach to surviving in his new environment. Meanwhile, Joy (Jaime Pressly) finds out, after a few failed attempts, the perfect gift to pay Earl back for taking her spot in jail comes in the form of taking care of Randy (Ethan Suplee), who is also having a hard time adjusting to his new life without Earl. In prison, Earl is sought out by a bully, who has lived most of his life in jail as a result of Young Earl's mischief. This new life for Earl behind bars must mean years of bad karma or does it?