This conversation addresses the social meanings and aesthetic role of the N-word in stand-up comedy, where its power, utility, and relation to Blackness are hashed out in performances and in dialogues among artists. We turn our attention to stand-up comedy as a vital cultural space for deconstructing and repurposing the N-word. We discuss how the stand-up comedian, as a sociopolitical commentator who subverts audiences’ expectations and calibrates sets through ongoing exchanges with the audiences, uses humor to wrestle with discomfort surrounding the N-word. Our dialogue focuses on the work of Richard Pryor, Chris Rock, Dave Chappelle, Wanda Sykes, and Sam Jay, with some consideration of Louis C. K., George Carlin, and Hasan Minhaj. We make the case that to discuss the N-word in stand-up comedy is to engage with public understandings of Blackness and humanity.