This chapter identifies two recurring themes that, beginning with Teodoro Ramos Blanco and Alberto Peña in the 1920s–1930s, has continued to define the conceptual basis of many Afro-Cuban artists up to the present. One is their efforts to conceptualize and celebrate their African cultural heritage. The other direction focuses on Afrodescendants’ social conditions and engages with political struggles against structural racism. Challenging the established historical arc accepted by the scholarship, the chapter identifies the 1940s as the most radical moment of Afrodescendant rupture in Cuban arts. It involved the revolutionary visual language of Uver Solis, Roberto Diago Querol, and Wifredo Lam, as well as the reformist executions of unknown artists such as Nicasio Aguirre, grounded on ideas of racial inclusion and black honorability. It also questions the assumed divide between pre- and post-1959, noting how revolutionary institutions continued to function under the common sense of the superiority of Western-centric art. It points to how the defining feature of the supposedly “new” revolutionary art, socially engaged figurative expression, was long established in Republican Cuba. The serious explorations of African-based cultures pioneered in the 1940s also continued in the 1960s–1970s with Grupo Antillano.