The Fromm–Marcuse debate in Dissent magazine published in 1955–56 was a defining moment in the intellectual careers of both theorists, and has helped define the reception of Freud for Frankfurt School scholars for over 50 years now. The literature on this debate about psychoanalytic theory and radical politics gave rise to numerous polemics between pro-Fromm and pro-Marcuse partisans, much of it now outdated as critical theorists have come to understand that they have more in common with each other than with mainstream social sciences. This chapter reviews the history of this theoretical debate on the status of Freudian theory in critical theory, and offers a synthetic reappraisal of the insights both theorists offer for a contemporary analysis of character and authoritarianism in light of contemporary debates within psychoanalysis and recent developments in Frankfurt School scholarship on the ideas and careers of both Fromm and Marcuse. The chapter discusses what a critical theory of authoritarianism offers social philosophy and social sciences in the contemporary context of capitalist crisis, cultural chaos, violence and impending environmental disaster.