This dissertation reconsiders the relationship between fiction and slavery in American literary culture. “Prisoners of Style” shows how writers from the middle of the nineteenth to the middle of the twentieth century, including Hannah Crafts, Mark Twain, Charles Chesnutt, and William Faulkner, wrestled with enslavement. They found it not only a subject to be written about, but also a problem of characterization. Slavery and the ontological sorcery through which it produced a new kind of individual—the individual who is also a thing—led these authors to rethink basic formal assumptions about realist fiction, especially about what constitutes a literary character. The writers I discuss did not set out to argue for the slave’s humanity or to render her interiority, but instead sought to represent the systematic unmaking of black personhood perpetrated by the laws and institutions that governed chattel slavery in the US. They set out to reveal the ideological violence perpetrated against enslaved blacks, and they did so by writing characters who embodied the categorical uncertainty of the slave, characters who were not allegories for real, full people. The tradition of writing I describe does not represent the fullness of enslaved “persons”; instead it renders something far more abstract: the epistemology that undergirded enslavement—those patterns of thought that preconditioned slavery itself. The authors I study understood fictionality as a thorny ethical, epistemological, and political problem. In my chapter on Crafts, for example, I look at The Bondwoman’s Narrative alongside a set of non-fiction texts about Jane Johnson, the slave who preceded her in John Hill Wheeler’s household. Reading the novel against legal documents, pamphlets, and histories about Johnson and her escape from Wheeler, the chapter explores what fiction could do that these other modes of writing could not. In moments of sleep, amnesia, and daydreaming, Crafts resists the normative logic of subjecthood and individual rights that underpins the representations of Johnson. In the second half of the project, I demonstrate the significance of fictionality to American literary realism’s evolution into modernism. The final chapter, on Faulkner, places two of his Yoknapatawpha novels within the context of his interest in modernist painting and sculpture. Work by Picasso, Matisse, and other visual artists inspired his concern with surfaces and flatness, leading to a meditation on artifice that runs throughout his major novels. I argue that his flatness—his insistence on the non-referential quality of fiction—is crucial for understanding his characterization and philosophy of history history, in particular the history of Southern plantation slavery.