As soon as he steps on stage in the Prologue, BJJ introduces himself as a “Black playwright,” though he also asserts that he does not know what this term means. Though Branden Jacobs-Jenkins’s work often explores constructions of race and racism as an ongoing theme, and this is particularly true with An Octoroon, the implication is that he is never sure how to define the expectations that come with the label “Black playwright.” Faced with the conundrum of finding no white male actors willing to perform in such an unfashionably melodramatic play, BJJ takes on the roles of both the white protagonist and the white villain, for which he puts on whiteface makeup. Whiteface, which certainly doesn’t produce the same cultural gut-punch as the blackface that was used in the original Boucicault melodrama, serves as a reminder of race as a constructed set of social hierarchies.

Jacobs-Jenkins plays with the visibility and invisibility of race, commenting on how race can often be difficult to quantify or definitively identify while also having immense material consequences. Whereas whiteness is often treated as invisible, or as the racial norm or default, white makeup on a Black actor makes it forcefully visible.