Boondocks follows Huey, a 10-year-old revolutionary-in-training, and Riley, his 8-year-old brother and future gangsta. The boys have been moved from their home on Chicago's South Side to the suburban "boondocks" to live with their grandfather, where they get into trouble and comment freely upon the idiosyncracies - to put it mildly - of the white people in whose culture they are now immersed.

Granddad sneaks the boys into the movies to be cheap. Sarah's obsession with Usher after meeting him threatens her relationship with Tom. Riley and Granddad refuse to talk with cops about two local thieves, even after Granddad's car is stolen. Stinkmeaner's spirit possesses Tom and he tries to get revenge on Granddad. Riley joins the basketball team, and the boys fight over who will be boss while Granddad's on vacation.