Robert and Riley enlist A Pimp Named Slickback (voiced by Katt Williams ) to teach Tom "assertiveness" through a crash course in "chronic bitch dependency".
The Boondocks episode remains one of the series' most iconic satires, blending celebrity worship, relationship dynamics, and a legendary guest appearance (of sorts) into a twenty-minute masterclass in cringe comedy. The Real Story Behind the Satire [S2E2] Tom, Sarah and Usher
In one of the show's most famous musical moments, Tom breaks into a stylized, clumsy version of Usher's "Burn," complete with a backup choir. Robert and Riley enlist A Pimp Named Slickback