Toni Morrison, in Playing in the Dark, observes the pervasive silence that surrounds race in nineteenth-century canonical literature. Observing the ways in which the “Africanist” African-American presence pervades this literature, Morrison has called for an investigation of the ways in which whiteness operates in American canonical literature. This thesis takes up that challenge. In the first section, from Chapters One through Three, I explore how whiteness operates through the representation of the African-American figure in the works of three eminent nineteenth-century American writers, Harriet Beecher Stowe, Walt Whitman, and Mark Twain. The texts studied in this regard are: Uncle Tom’s Cabin, Leaves of Grass, and Adventures of Huckleberry Finn. This section is not concerned with whether these texts constitute racist literature but with the ways in which the study of race, particularly whiteness, reveals the contradictions and insecurities that attend (white American) identity. As such, Morrison’s own fiction, written in response to white historical representations of African-Americans also deserves attention. The second section of this thesis focuses on Morrison’s attempt to produce an authentically “black” literature. Here I look at two of Morrison’s least studied but arguably most contentious novels particularly because of what they reveal of Morrison’s complex position on race. In Chapter Four I focus on Tar Baby and argue that this novel reveals Morrison’s somewhat essentialist position on blackness and racial, cultural, and gendered identity, particularly as this pertains to responsibilities she places on the black woman as culture-bearer. In Chapter Five I argue that Paradise, while taking a particularly challenging position on blackness, reveals Morrison’s evolving position on race, particularly her concern with the destructive nature of internalized racism. This thesis concludes that while racial identities have very real material consequences, whiteness and blackness are ideological and social constructs which, because of their constructedness, are fallible and perpetually under revision.