|Season 3, Episode 9(39)|
|Air date||June 27, 2010|
|Written by||Aaron McGruder|
|Directed by||Young Chan Kim|
|The Boondocks Season 3|
|May 2, 2010 – August 15, 2010|
The Story of Lando Freeman
As a punishment for fighting, Huey and Riley have to attend a "Scared Stiff" program at William Horton Prison. Tom Dubois, having recently conquered his phobia of "being sent to prison and anally raped", volunteers to lead the group. The session quickly devolves into an in-depth discussion of committing prison rape, culminating in the Scared Stiff prisoners instigating a full-scale riot which Tom caused because he brought a sharpened toothbrush to the prison. The prisoners are taking the children and Uncle Ruckus hostage while Tom escapes.
As the Scared Stiff prisoners (who have styled themselves "The Executive Riot Committee") formulate demands, Tom leads Ruckus and all of the white children to safety. Realizing that the Freeman boys are missing, Tom returns for them, only to encounter the Booty Warrior in a shower room. Tom fights and defeats the Booty Warrior.
The Executive Riot Committee, noticing that their hostages have escaped, vote to disband and surrender to authorities. Tom arrives and he and the Freeman boys leave the prison.
- The introduction of this episode parodies the Dateline NBC series "To Catch A Predator", where investigator Chris Hansen confronts chat room predators looking to set up sexual liaisons with minors.
- Tom marches in a rally against Proposition 8, a 2008 constitutional amendment which initially banned same-sex marriage in California (it was overturned in 2013). He also references Sean Penn playing assassinated San Francisco politician Harvey Milk in the 2008 film Milk.
- YouTube clips of Fleece "Booty Warrior" Johnson from Lockup and the "Tossed Salad Man" are parodied throughout the episode. Both characters, especially Fleece Johnson, are satirized.
- Before the Booty Warrior tosses a bar of soap at Tom in the shower room, he says "Tom, come out to play" a reference to the movie The Warriors.
- William Horton Prison is named after American convicted felon Willie Horton.
- Director John Landis guest stars in the show.
- The Attica Prison riot is referenced to during the prison riot by one of the prisoners after he realizes that there was no plan beforehand by stating "I thought this was suppose to be some Attica type shit!"
- The "Scared Stiff" program parodies and satirizes the "Scared Straight" programs, portrayed in film and television.
- Tom's fear of being raped in prison is first introduced in the Season 1 episode, "A Date With The Health Inspector".
- This episode features Butch Magnus' third appearance and his second appearance with no dialogue.
- This is the second time Huey attempts to organize social activism for an organization of strangers. The first was in "...Or Die Trying".
- The word "pause" is used several times in the episode, referencing the previous episode "Pause".
- Tom finally conquers his fear of prison rape.
Leonard Pierce of The A.V. Club graded the episode a B. Pierce called it "a flawed episode, but still a vast improvement over its season 1 predecessor" but found it to be "a bit of a step back from the rolling thunder of the last month or so, with a bit too much padding and a pretty trite confrontation at the end, but only in comparison -- it's better than most of what we got in season 1, and certainly isn't a loser".