This chapter examines the work of Richard Pryor and his comic successors, who build on his work while taking it in dynamic and unprecedented directions. In particular, this chapter focuses its attention on comedy albums that combine the live stand-up of the comics with recorded bits that reinforce critiques in other forms. So, Pryor’s Bicentennial Nigger uses skits to help reject the romanticized narrative of the United States at the bicentennial. One of the most immediate successors to Pryor was Whoopi Goldberg, whose Direct from Broadway pulls from the template that Moms Mabley constructed by directly confronting the oppression that sits at the intersection of race and gender. However, Goldberg expands on Pryor’s work not through the inclusion of a female voice but by transforming the exploration of black life into a female-centric critique of white, Western, supremacist, patriarchal hegemony. This chapter argues that Chris Rock most effectively realizes Pryor’s legacy of comic rage. Rock’s work, from Bring the Pain (1996) to Never Scared (2004), engages directly with the historical moment of post–civil rights America and is most clearly represented in Rock’s infusion of hip-hop into the structure and style of mainstream stand-up comedy.