This study explores the reciprocal relationship between technology, politics, and the arts. When computers brought about an automation of mental work, it became imaginable, as well as practicable, to use computers to produce verbal and visual art, as well as certain types of dramatic performance. Responses of artists diverge, however: one embraces the automating potential of the computer, and another resists it. By contrasting the work of novelist J.M. Coetzee and artist William Kentridge, I extend research on automation to wider cultural understandings of computing—among them, the ethical and political meaning given to automation (whereby tasks previously done by workers are done by machines), and to human–computer interaction. The peculiar meaning given to automation and computerization in apartheid South Africa, where the labor market was distorted by racial “job reservation,” I argue, profoundly informs the diverging responses of these two South African artists.