The Boondocks S03 E09 A Date with the Booty Warrior

"Satire, chaos, and black humor."

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 has to get the kids, and his delicate backside, out of jail in one piece.