In the 1930 novel Not without Laughter, Langston Hughes represents Black life in the Midwest through the experiences of Sandy Rodgers and his family in small-town Stanton, Kansas (a stand-in for Hughes’s childhood home of Lawrence, Kansas). Much of the criticism on Not without Laughter focuses on the influences of Sandy’s grandmother and aunts, but this chapter centers his father, Jimboy. While he rarely instructs Sandy on how to be a man, Jimboy models a Black blues masculinity that draws together multiple aspects of early twentieth-century American culture. By reading Jimboy within the novel’s Midwestern cultural and historical context, this chapter foregrounds him as a consequential figure within both the novel and Sandy’s life. Jimboy’s demeanor, musicality, and mobility suggest how Sandy might learn to cope with life in the modern Midwest – notably, however, in ways that do not align with the conventionally respectable aspirations of his female relatives.