Since the 1920s, American writers have evinced a fascination with and investment in fictional representations of jazz music and jazz musicians. As this essay demonstrates, part of jazz’s appeal for fiction writers is that it offers the opportunity to explore various kinds of border crossing. This essay surveys several jazz fictions to explicate how these fictions portray jazz as a local event, often focusing on musicians who may not be known beyond their own communities, but who live to play the music. Using Nathaniel Mackey’s concept of artistic othering, this essay investigates how writers portray the jazz musician’s search for a space to belong, where artistic forms of risk-taking are affirmed and the contingencies jazz musicians face, whether it be in the form of substance abuse, underemployment, self-doubt, or social injustice can be managed through instances where self-repair, improvisation, and community constitute the foundations of the musician’s lifeworld. Jazz fiction, in other words, is deeply concerned with the contradictions of American life and how playing jazz music involves the act of containing contradictions.