The article presents a comparative analysis between Paulo Freire and Erich Fromm. The introduction is focused on the great importance of studying and interpreting Freire’s work nowadays and its contribution to Pedagogy and other fields. The article presents a synthesis of both Freire and Fromm’s biographies and some similar aspects that emerge, such as their experience with religion, the study of Marxism and their life in exile. Afterwards some key concepts used by the authors are analyzed. Their approaches to education, freedom, oppression, awareness and emancipation converge in many aspects and can be complementary and useful in several ways for contemporary studies.