To what extent is Roland Barthes relevant to a significant discussion of “Afro-modernity,” especially as a theorist of language and culture? Barthes wrote, “To be modern is to know clearly what cannot be started over again.” This is the crux of the dilemma faced by theorists of modernism and postmodernism within the context of the African diaspora—an atemporal space of contestation. This chapter explores the problematic of ancestrality and the dynamics of Afro-modernity in the Brazilian context and by extension in the African diaspora. It ponders the legitimacy of “modernism” and “postmodernism” with particular emphasis on Afro-Brazilian cultural producers before and after the Semana de Arte Moderna of 1922. What is “modernity” for Afro-Brazilians? Why was the Afro-Brazilian excluded from participation in the significant literary and cultural movement of 1922? Why was the representation of the Afro-Brazilian limited to a cosmetic presence in Brazilian letters up to 1922 and after? How were the emerging writers of the time able to “correct” or challenge this situation? And how have contemporary writers defined themselves in terms of “modernity” and “postmodernity”? Roland Barthes's provocative assertion is indeed relevant, for it brings to the fore the dilemma of definition and application in the Brazilian context where these Western terminologies are not applicable. If “modernity” is defined as what cannot be started again, then it is the opposite of the African diaspora, by its own “definition” the regrouping of people of African descent in a new location other than where they originated.