The Boondocks (2005)

S3E9 A Date with the Booty Warrior

After overcoming his anxiety about prison rape, Tom decides to take the initiative and lead Huey, Riley, and a few classmates on a field trip to jail as part of the Scared Stiff program. However, chaos ensues when a riot erupts, forcing Tom to find a way to safely escort the kids—and himself—out of the chaotic situation without any harm coming to them.