Gary is falsely accused of beating his insane ex-girlfriend Charlotte, and he is sentenced to 30 days in Merkin Penal, a privately run prison. Once behind bars he runs into his old friend Smitty, who's in the 2nd year of his 9 month stay, due to a run in with the TSA. Smitty is "insane Charlotte's" older brother. Smitty and Gary met while Gary and Charlotte were an item. They are forever bonded together by their shared celebration of hatred for Charlotte. After a First Class, welcoming tour of the prison via Smitty, and a run-in with Emmett O'Donald, from upper Prison Management, Gary realizes his original sentence of 30 days was all Bulls@!t. He may never get out.