In “Creeping into the Conversation,” I examine canonical texts from the African American Literary Tradition, including Ann Petry’s The Street (1946) and Toni Morrison’s The Bluest Eye (1970), alongside contemporary, oft marginalized novels, including Sapphire’s PUSH (1997), and Sister Souljah’s The Coldest Winter Ever (1999). This project considers literal and figurative streets as historical markers of class, race, and socio-economic status, but also as a link between literary periods. Placing canonical literature in the same conversations as “street literature” and Hip Hop literature is a way to diversify critical conversations in contemporary African American literature. Embracing street literature and Hip Hop literature as parts of a larger critical conversation provides a lens through which one can examine the cultural, racial, and political impacts they have in popular culture and in academia. “Creeping into the Conversation” is an intertextual study which showcases diverse conversations among texts across a large trajectory of African American literature. These diverse conversations give fresh insight to texts already considered mainstays in African American literature. Additionally, these intertextual analyses bring more contemporary narratives and authors into academic discourses. On the whole, “Creeping into the Conversation” bridges the gap between the critical and the literary in contemporary African American literature.