The aim of this article is to analyze W.E.B. Du Bois's educational thought for its key contributions to contemporary Africana philosophy of education. To succinctly explore Du Bois's philosophy of education, the article outlines some of the ways his pedagogical theories and practices are inextricable from, and virtually incomprehensible without critically considering, his philosophy of history, concepts of culture, economic thought, and social and political philosophy. Arguing that many scholars have both masked and marred Du Bois's contributions to philosophy of education by focusing almost exclusively on his "talented tenth" theory, this study examines his educational thought after he produced the classic, "The Talented Tenth" (1903), essay. The article advances that Du Bois's revision of the talented tenth into a theory of the "guiding hundredth," which stresses struggle, sacrifice and service, group leadership, and African historical and cultural grounding, provides Africana philosophy of education with a pedagogical paradigm and provocative point of departure.