Let's Go to Prison

Let's Go to Prison is a 2006 comedy film starring Dax Shepard and Will Arnett. The movie was loosely based on the non-fiction book, You Are Going to Prison by Jim Hogshire.

Since John Lyshitski (Shepard) was eight, he's been in and out of prison, all because of one man--Judge Nelson Biederman III. (Well, okay, it's mostly his own fault, but Biederman's sentences are indiscriminately harsh.) Lyshitski plots his revenge while completing his third sentence, only to find out that Beiderman died three days prior to Lythitski's release. So, to get revenge on Biederman III, Lyshitski decides to get the obnoxious rich-kid Nelson Biederman IV framed for theft. It works, mostly due to Biederman's lawyers intentionally sabotaging the case, and Lyshitski gets himself locked up in the same prison to insure that Biederman has the worst time possible.

Tropes used in Let's Go to Prison include:

Affably Evil: The entire time the neonazis are portrayed as polite, stick together, listen to orders without question, and as said by the abused henchmen "He was giving neonazis a bad name!"
Break the Cutie: Lampshaded Nelson
Chewbacca Defense: What Biederman IV's lawyers use to insure he's locked up; they claim that Biederman's crime was just a special effect.
Cluster F-Bomb: Biederman when he loses his case and gets hauled off to prison.
Complete Monster: Well the movie IS set in a prison. However, special mention must go to Leonard, the swastika tattooed, father killing, drug shooting, neonazi leader of the "White Kingdom."
Crowning Moment of Funny: Barry threatening that he will cut Biederman's nuts off and put them in a shoebox. Twice.
Dirty Cop: The prison seems to be full of them. Even the warden wanted to put money on Lyshitski and Biederman's big fight.
Driven to Suicide: Nelson at one point decides to end it with a lethal injection he obtained at one point. He's interrupted by Leonard, who mistakes the needle for Heroin and kills himself with it.
Does This Make Me Look Fat?: Barry asks Nelson if his butt is big when the latter says no Barry threatens him with a knife.
Even Evil Has Standards: Even the "White Kingdom" neonazi gang thinks that their former Complete Monster leader Leonard is a guy who "gives neonazis a bad name."
Get Into Jail Free^[context?]
Hey, It's That Guy!: GOB is Biederman IV.
Jerkass: Both Lyshitski and Biederman are assholes.
Magnificent Bastard: Biederman by the end.
Manly Gay: Barry.^[context?]
Nice Guy: Barry after he and Biederman become "close friends."
Prison Rape: Subversion. Scary Black Man Barry actually woos Nelson with toilet-made Merlot and a romantic environment in his cell. They eventually become life partners.
Scary Black Man: Barry at first.^[context?]
Invisible to Gaydar: Barry and Nelson's sexualities are never put as the focus of their characters, and the most flamboyant thing about either of them is their affinity for toilet wine.
Those Wacky Neo Nazis: The White Kingdom.