Having conquered his fear of prison rape, Tom volunteers to lead Huey, Riley, and some classmates on a trip to jail as part of a "Scared Stiff" program, but when a riot breaks out, Tom is pursued by an imprisoned rapist while trying to get the kids out safely; during the riot, Huey and Riley help black prisoners organize a riot committee that makes outrageous demands.
Tropes:
- An Aesop: One of the rioting prisoners, exhausted from their botched hostage situation, confides in Huey and Riley that he deeply regrets the criminal decisions he made that caused him to wind up in prison."You know, I spend a lot of time, you know, thinking about all the shit I could've done. I mean, I wake up in the morning and I think, I could've been the motherfucking president. Shit. Nigga, I wish things had've been different. I mean, I'd do anything in the motherfucking world just for things to be different. I guess I'm just gonna be raping niggas' asses for the rest of my motherfucking life."
- But Not Too Black: Tom's "medium-brown" skin is noted to be an attractive quality by the prisoners.
- Cluster F-Bomb: The prisoners are incredibly foul-mouthed, but their argument on who should be the "chief executive" stands out.
- Deliberate Values Dissonance: The prisoners decide to call off the riot after they realize that Tom helped most of the children (and Ruckus) escape, implying with their speech of having "no hostages" that they don't consider Huey and Riley to have any "strategic leverage" as black kids.
- Double Standard: Rape, Male on Male: Played straight in the Cold Open. Discussed throughout the episode, and averted by Tom against the Booty Warrior. Both Played for Laughs and Played for Drama.
- Even Evil Has Standards: The prisoners are proud rapists but they balk at the suggestion they would do so to children.
- Manly Gay: Booty Warrior is a dark example of this, but even some of the prisoners talking at the seminar rudely express genuine attraction to Tom rather than simply seeing his rape as a way to display manhood or pass the time.
- Missing Episode: In-universe example; the Cold Open shows a clip from an unaired 2005 episode of Dateline: To Catch a Predator, where Chris Hansen confronts the Booty Warrior on trying to have sex with a minor. The criminal has no issue accepting his arrest, but there's one little problem. The criminal was never after the boy. He was actually interested in a "man's butt", specifically Hansen's. As a result, Hansen himself ends up anally raped onscreen.
- Scare 'Em Straight: Tom takes the Freeman boys and some other school students to a local prison for this purpose, but it goes south in a hurry. However, Huey and Riley at least get to learn how awful it is to be in jail and how much they'd regret making the choices that land them there when one of the inmates tiredly lets himself be vulnerable with his angst.
- Took a Level in Badass: Tom not only faces his fears of getting anally raped in prison, he manages to defeat the Booty Warrior to literally save his butt.
