A concentrated analysis of Branden Jacobs-Jenkins’s play An Octoroon (2014), this chapter explores how representations of Black people have been utilized and appropriated by white America. Jacobs-Jenkins uses minstrelsy-style theatre and lynching photos to force the audience into recalling a past when people of color were corporeally represented on stage by white actors in colored face paint. In a manner similar to the play on which Jacobs-Jenkins bases his play – The Octoroon (1859) by Irish playwright Dion Boucicault – An Octoroon debuted at a time when the American political landscape was fraught with civil and racial unrest; Jacobs-Jenkins uses humor, Brechtian theatrical devices, and self-referential framing to illustrate how the threat of violence functions in modern America to debilitate Black Americans and maintain the construct of racial hierarchism.