The Boondocks - Season 3 - Eps 9: A Date with the Booty Warrior
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.
About The Boondocks

Title: The Boondocks
First Air Date: 2005-11-06
Last Air Date: 2014-06-23
Status: Ended
Rating: 8.1/10 (from 366 votes)
Language: EN
Seasons: 5
Total Episodes: 55
Network: Adult Swim
Genres: Action & Adventure, Comedy, Animation
Production Companies: Sony Pictures Television, Adelaide Productions, Rebel Base, Sony Pictures Animation
Synopsis
When Robert “Granddad” Freeman becomes legal guardian to his two grandsons, he moves from the tough south side of Chicago to the upscale neighborhood of Woodcrest (a.k.a. "The Boondocks") so he can enjoy his golden years in safety and comfort. But with Huey, a 10-year-old leftist revolutionary, and his eight-year-old misfit brother, Riley, suburbia is about to be shaken up.
Cast

Regina King
Huey Freeman / Riley Freeman (voice)

John Witherspoon
Robert Freeman (voice)

Cedric Yarbrough
Tom Dubois (voice)

Jill Talley
Sarah Dubois (voice)

Gary Anthony Williams
Uncle Ruckus (voice)

Gabby Soleil
Jazmine Dubois (voice)