This chapter discusses how an unusual group of works, featuring a character nicknamed Simple, help us think about the complexities of Black political consciousness. The Simple stories appeared in the Chicago Defender over the course of twenty-three years, and were also collected in The Best of Simple and other volumes. Characters therein debate race and class from the local standpoint of the neighborhood of Harlem and extending into other worlds. Hughes’s movement across literary genres (having written in so many) takes shape in these stories as a question about the porous boundary between realist and imaginative modes, when Black people are pondering the limits of freedom and mobility. And the resemblance between Simple’s main interlocutor, an intellectual narrator, and the author is an example of how Hughes sees himself as implicated. Ultimately, in formalistic and affective terms, the Simple stories advance multiplicity as central to the experience of Blackness.