This chapter describes how much of early African American literature takes shape within competing demands and analyzes how early Black writers negotiate it. Indeed, many early African American writers produced their works within a literary double bind that pressured them to be truthful, to write with the highest level of exactitude, to imitate reality precisely, and to produce perfectly mimetic texts; and at the same time, to use their imagination, to create something beautiful, and to produce an aesthetically valuable text. I explore how George Liele, David George, Boston King, and Venture Smith negotiate this literary double bind at the end of the eighteenth century, a time that saw significant historical transitions including the Zong massacre, the American Revolutionary War, the ratification of the US Constitution, and the French and Haitian Revolutions, all against the backdrop of transatlantic slavery and efforts to eradicate it. In these narratives, although white editors, amanuenses, and interlocutors claim that these texts tell the “simple truth,” each exceeds and problematizes the description that emphasizes the texts’ transparent mimetic exactitude by creatively utilizing literary structures of expression, rupturing what Christina Sharpe describes as the episteme of racial slavery.