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 Lyshitski's release. So, to get revenge on Biederman III, Lyshitski decides to get the obnoxious rich-kid Nelson Biederman IV (Arnett) 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 ensure that Biederman has the worst time possible.
This film contains examples of:
- Accidental Suicide: When Nelson gets on the wrong side of Lynard, the leader of the white supremacist gang, he decides to kill himself by injecting a deadly chemical into his veins. Before he can do it though, Lynard enters his cell to kill him. Lynard sees the syringe, assumes it to be heroin, and injects himself with it. The other white supremacists, thinking Nelson killed Lynard, now respect him.
- Affably Evil: With the exception of Leonard, the Neo-Nazis are portrayed as polite, stick together, listen to orders without question, and as said by the abused henchmen "[Leonard] was giving Neo-Nazis a bad name!"
- Briar Patching: Used by Nelson on Leonard. Leonard found a syringe filled with poison Nelson was going to use to avoid facing the former. Nelson, thinking on his feet, convinced Leonard that it was heroin, causing him to inadvertently commit suicide. Even discussed shortly, after the fact.
- Butt-Monkey: Biederman, oh so much. That is, until he gets Leonard killed and begins to grow a spine.
- Chastity Couple: Nelson and Barry. Despite Barry's earlier desire to "butt fuck" Nelson (as he put it himself), he seems perfectly fine with not having sex. Simply being in Nelson's company is more than enough for him.
- Chewbacca Defense: What Biederman IV's lawyers use to ensure he's locked up; they claim that Biederman's crime was just a special effect, comparing the security-camera footage of the robbery to Jeff Goldblum getting eaten by a dinosaur in Jurassic Park.
- Cluster F-Bomb: Biederman when he loses his case and gets hauled off to prison.
- Dirty Cop: The prison seems to be full of them. Even the warden wanted to put money on Lyshitski and Biederman's big fight.
- The Dreaded: After getting the credit for Leonard's accidental suicide by boat cleaner, this becomes Nelson's general reputation, everyone having assumed it was the violent murder of the former most dangerous man in prison.
- 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, telling Nelson to never lie to him again.
- Even Evil Has Standards: Even the "White Kingdom" neonazi gang thinks that their former leader Leonard is a guy who "gives neonazis a bad name."
- Everyone Has Standards: Barry is appalled by Nelson wanting to abandon Lyshitski, who is still buried alive after their escape plan, and convinces him to do the right thing simply because it’s bad karma on Nelson’s part.
- Faking the Dead: Biederman and Lyshitski do this to get out of prison in the end.
- Faux Yay: Nelson, after making peace with Barry
- Foreshadowing: As Lyshitski and Biederman enter the prison, Lyshitski comments that there's only one way to get out quickly: in a body bag. Eventually, that becomes the crux of their escape plan.
- Get into Jail Free
- Hanging Judge: Judge Biederman III is ridiculously harsh.
- In Name Only: The movie claims to be adapted from the book "You Are Going To Prison" by Jim Hogshire, a work of nonfiction in which the author gives advice for those going through the legal system, from arrest, trial and incarceration. While a few of its lines are quoted in the movie, the book is devoid of narratives and characters.
- Jerkass: Both Lyshitski and Biederman are assholes, though Biederman is definitely the lesser of the evils.
- Jerk with a Heart of Gold: If Nelson saving Barry, a man who has repeatedly harassed him, from being attacked by Nazis is any indication - he isn't completely heartless.
- Jerk with a Heart of Jerk: Leonard - in Lyshitski's words: "Don't be fooled. Underneath all those swastikas, he's a real prick."
- Loophole Abuse: Nelson is automatically made chairman of his father's foundation after his father's death, per the foundation's rules to transfer control to Biederman's son, but is then automatically removed from the chairmanship when he's convicted of a felony. He gets around this by using Barry’s love to his advantage. He legally adopts Barry as his son, making him chairman.
- Manly Gay: Barry. Later, Nelson fits this trope when he feigns homosexuality to avoid Barry’s wrath.
- Nice Guy: Barry, deep down. Especially after he and Nelson, the object of his affection, become the best of friends.
- Phrase Catcher: Biederman's 'tough face', which prompts everyone who sees it to comment that he looks like he "has to take a shit."
- Prison Rape: Subversion. Scary Black Man Barry forces heterosexual Nelson into a relationship with threats of extreme violence shall he ever lie or reject his advances. However, Barry does try to woo him with toilet-made Merlot and a romantic environment in his cell. They eventually form a genuine friendship, which prompts Nelson to just play along with the “relationship”. However, Nelson’s facial expressions and awkward body language strongly hints that he is still uncomfortable with Barry’s affection.
- Scary Black Man: Subverted with Barry. Though he can be scary, he's actually quite the romantic.
- Sinister Shiv: An inmate gets stabbed right in the cafeteria right at Biederman's table on his first day. Later in the movie Biederman and Lyshitski are trying to shiv each other in a prison fight orchestrated by the guards for entertainment.
- Sins of Our Fathers: With the judge that repeatedly sentenced him dead, Lyshitski decides to get revenge on his son instead.
- Straight Gay: Barry's sexuality is never put as the focus of his character, and the most flamboyant thing about him is his affinity for toilet wine.
- Those Wacky Neo Nazis: The White Kingdom.
- Unishment: Well, Lyshitski did want to go to prison the fourth time. Also Biederman going to the hole... Until it drove him crazy at least.
- Unsympathetic Comedy Protagonist: Lyshitski, and to a lesser extent, Nelson.
