This dissertation is an examination of the trickster paradigm--an aesthetic, a principle that is specific to black creativity and narration and an enabling force behind the subversive rhetorical strategies of "Signifyin(g)" or double-voicedness that I trace in the African American vernacular and literary tradition. Through an analysis of the works of Zora Neale Hurston, Langston Hughes, James Baldwin, Melvin Tolson and Toni Morrison, I outline a theory of the trickster principle that is operative on several levels. My project relies on a reading of the trickster as a culture hero--figure of mediation and resistance--and codifies the importance of this figure as a "signifier" in black consciousness that has endured over centuries, encompassing acts of subjugation and transformation in response to historical changes. In addition, my discussion of the trickster tradition opens up a larger argument pertaining to the dynamics of vernacular/literary production and the ability to respond to the demands of American modernity--in terms of mobility, urbanization, industrizalization, etc. I also trace how these processes of reclaiming and recovery of vernacular expressive modes and their use in written literature reveal the unsettling issue of not just coming to terms with American capitalist modernity, but also with the American modernist literary canon. Finally, the last chapter suggests a "transnational turn" as I look into the specifics of cultural contacts between two geographically distant literary traditions--the African American and the Macedonian-- and their respective engagements with their folk past. This analysis brings to the fore the peculiarities of historic relatedness and a shared articulation of a people's "spirit" in traditions that respond to the violence and annihilation of enslavement and colonization. This kind of globalization of African American literature and theory opens up a new, exciting possibility to read black literature beyond the transatlantic and transdiasporic frames. It adopts a transnational approach that emphasizes connections among "minority literatures" across nation-states and re-defines the scope of a new global multiculturalism.