Despite striking similarities in their work and increased attention to the transnational Americas, there are few detailed comparisons between writers such as Toni Morrison (the most lauded African American female author of the twentieth century), and Jamaica Kincaid (the most critically and commercially successful female Caribbean writer). For example, the common approach to examining Morrison's groundbreaking novel The Bluest Eye (1970) is to foreground its national significance, or, less frequently, to apply its discourses quite generally and loosely to other cultural contexts like Latin America. However, building on relatively recent attempts to locate Morrison in broader transnational spaces, in this discussion, I propose closely examining a text from another Anglophone, African diasporic context, which utilizes many of the strategies evident in Bluest —Kincaid's Annie John (1985). By engaging the larger English-speaking Americas, such an approach highlights the transnational implications of the race and gender paradigms Morrison deploys; also, although Annie John is commonly categorized as primarily Caribbean (a precursor to Kincaid's “American” sequel, Lucy ), my proposed comparison elucidates the Western and transnational leanings of this foundational “Caribbean” work and the ways in which it implicitly expands on Morrison's representations of female autonomy and visual culture. To that end, I borrow from and expand on Cheryl Wall's notion of “worrying the line” (Wall 2005)—black women writers' emphasizing, clarification, and subversion of literary traditions—to examine how black women in different cultural contexts write themselves into visual and historical records. Contributing to burgeoning interest in the Americas as a transnational space, I argue that Kincaid appropriates Morrison's treatment of visual culture, gender, and identity, presenting similar dynamics in another African diasporic community and depicting even more autonomous female characters.