This chapter examines fictional depictions of African American presidents as a popular trope in U.S. film, television, and literature, as producing a discourse of “black presidentialism” that implicitly embeds a logic of passing that comes into relief in sketch-comedy performances by Richard Pryor and David Chappelle. This chapter argues that Chappelle’s “counterburlesque” as “Black President Bush,” which rearticulates George W. Bush’s Iraq War policy and its justifications rearticulates in terms of black hypermasculinity and street vernacularities, exposes how popular culture’s discourse of black presidentialism, in its post–Civil Rights era instantiations, invokes what the traditional passing narrative understands as the disconnect between its protagonist’s appearance and presumed essence of his or her identity, with acute attention to the role gender plays in racial semblance. In the case of the black president trope, that dualism is recoded as the tension between the abstracted white manhood of the office of the presidency and black masculine racial particularity.