This article presents one of the main theoretical results of a doctoral dissertation in Education developed in the light of Historical-Dialectical Materialism and Historical-Critical Pedagogy. Its central objective is to explicate the category of Artistic Problematization, preceded by the categories of Theoretical Foundation and Technical Instrumentalization, taking as its axis the concepts of artistic knowledge and aesthetic knowledge within the philosophical thought of education formulated by Dermeval Saviani and by Historical-Critical Pedagogy. By recognizing that the philosophical dimension of this theory organizes and guides the school educational process in its critical, artistic, and aesthetic dimensions, the study advances by proposing Artistic Problematization as the initial stage of pedagogical work. This stage articulates the students’ syncretic practice with the synthetic elaborations constructed by the teacher, in an intentional and dialectical movement aimed at elevating social practice to a level of elaborated understanding. The discussion is grounded not only in Saviani’s contributions but also in the foundations of historical materialism, especially in Karl Marx and Friedrich Engels, in addition to engaging with the Marxist aesthetic thought of Theodor Adorno and Adolfo Sánchez Vázquez. As a result, the article proposes critical-aesthetic pathways for the initial training of educators, organized in the triad Artistic Problematization, Theoretical Foundation, and Technical Instrumentalization. By highlighting the centrality of world aesthetics and art in the teaching–learning process, the research reaffirms the relevance of Historical-Critical Pedagogy for understanding human development and structuring educational practices that articulate theory, knowledge’s socialization and pedagogical action.