Black peoples’ influence on videogames’ historical development is often relegated to much later points in medium’s evolution (that is, after the 1960s). Nonetheless, Harlem Renaissance (about 1917–1935) literary figures like W.E.B. Du Bois, Langston Hughes, and George Schuyler meditated on questions at the root of future debates about race and videogames’ capacity for social change. Schuyler explores such questions through his satirical novel Black No More (1931) using a combined lens of race, technology, and play, where play is one vehicle for experiential world-building. Through a close-reading of Black No More alongside Canadian author Margaret Atwood’s ustopia complicating notions of good and bad outcomes in world-building, this chapter describes play as a racialized political activity rife with contradictory political potential. It complicates strict judgments about play experiences in that they either uphold or dismantle notions of race and racism. This essay argues that Schuyler’s meditation on race, technology, and play urges that we resituate Black artistic thought prior to the invention of videogames in the medium’s historical developmental trajectory. In doing so, this essay aims to offer scholars a literary method for exploring the videogame medium’s historical entanglements with race.