This article explores The Boondocks and its transition from daily newspaper strip to animated series. The article is particularly concerned with the ways in which the animated series exceeds the expectations set up by the printed comic strip and emerges as a complex, highly inter-textual work with a large number of subtle cultural references. In order to account for The Boondocks, transition from one medium to another, the animated series is analyzed via theories of appropriation and adaptation, with special attention paid to the series' deft cultural borrowing and the use of formal conventions typically associated with Japanese anime. The article also examines The Boondocks' relationship to The Simpsons, and establishes The Simpsons as an important forbear to The Boondocks in terms of realism and social commentary.