Since slavery, African and African American humor has baffled, intrigued, angered, and entertained the masses. Rolling centers Blackness in comedy, especially on television, and observing that it is often relegated to biopics, slave narratives, and the comedic. But like W. E. B. DuBois's ideas about double consciousness and Racquel Gates's extension of his theories, we know that Blackness resonates for Black viewers in ways often entirely different than for white viewers. Contributors to this volume cover a range of cases representing African American humor across film, television, digital media, and stand-up as Black comic personas try to work within, outside, and around culture, tilling for content. Essays engage with the complex industrial interplay of Blackness, white audiences, and comedy; satire and humor on media platforms; and the production of Blackness within comedy through personal stories and interviews of Black production crew and writers for television comedy. Rolling illuminates the inner workings of Blackness and comedy in media discourse.