This chapter explores the nonfiction of Toni Morrison, which explicates how she theorizes alienation. While this chapter grounds Morrison’s theorization of alienation in terms of her early readings of William Faulkner and Virginia Woolf, appearing in her often-overlooked master’s thesis from 1955, this chapter constructs how Morrison approaches alienation alongside bell hooks’s theorization of black looking relations. Like hooks, Morrison’s sense of black looking relations shapes how those that are alienated self-regard at the margins, as a way to keep a hold on life, if drawing upon bell hooks’s own early readings of Morrison’s The Bluest Eye and Sula from hooks’s often-overlooked doctoral dissertation from 1983. Just as Morrison’s 1955 thesis self-regards at the margins of Morrison’s body of fictional work, the same is true for hooks’s 1983 doctoral dissertation, which also self-regards at the margins of hooks’s body of theoretical work. At the heart of both hooks and Morrison are looking relations between the two about the dynamics of black female intellectual life, which self-regards at the margins by deploying an oppositional gaze.