This dissertation analyzes the use of satire in African American literature and culture in forming a new understanding of racialization in the 1980s through the 2010s. This "post-soul" moment, defined by authors who came of age post-Civil Rights Movement, in particular necessitates humor and the satirical as it opens up a space for play to accentuate the inherent instability and absurdity in racial categorization. By placing in conversation texts and performers as diverse as Jourdan Anderson's "To My Old Master;" damali ayo's How to Rent a Negro; Adam Mansbach's Angry Black White Boy; Percival Everett's Erasure; Lynn Nottage's By the Way, Meet Vera Stark; Mat Johnson's Incognegro and Loving Day; Chris Rock, Dave Chappelle, and Leslie Jones, it becomes possible to document the insistent satirical inclination in African American literature and to examine its trajectory from the 19th century to the 21st century. The historical trajectory of satire within African American literary resistance calls for a shift in an understanding of humor as potentially frivolous and stress that the political and social import of African American humor must not be disassociated from the laughter it inspires today. By reading these satirical texts in the contexts of historicity, postmodernism, and African American literary theory, it becomes possible and necessary to examine the evolution of African American humor as the position of African Americans to power shifts and simultaneously remains the same and as depictions of race and its significance have changed with the intent of the portrayals.