Philosophers and practitioners of education Paulo Freire (Brazil, 1921-1997) and Lorenzo Milani (Italy, 1923-1967) promulgated pioneering theories and practices akin to critical, multiple, and multimodal literacies pedagogies, and social justice. Although they were contemporaries, Milani and Freire neither met nor exchanged their views on education. This study explores the influence of their pedagogies in two public schools in Brazil and Italy. In addition, it facilitates a dialogue between the two educators’ work, as well as among those who either worked with them or are aligned with their philosophies. Nietzsche’s concept of genealogy is combined with the discourse and power theories of Foucault, Gee, and Janks, and these interwoven dialogues are augmented with a narrative approach in the process of analyzing interviews. For data collection, I spoke with scholars and practitioners who worked with Freire and Milani, and documented observations made during extensive visits to Milani- and Freire-inspired schools. This project combines case studies and ethnography methodologies. It also employs art-based representation and performance ethnography in the literature review through an imaginary exchange of letters both between the two educators, and between me and them. In my role as both researcher and participant, I have investigated the ways that Freire’s and Milani’s pedagogies foster critical consciousness in these school communities.