This project argues, even though twentieth-century Iranian intellectuals conceptualized their social discontent differently, and the critiques are scattered around different concerns, there is nonetheless a commonality that is shared across the selected critiques. I propose the selected social critiques of twentieth-century Iranian intellectuals can be interpreted as constituting different formulations of cultural alienation. I propose that Iranian intellectuals perceived alienation to be the result of a cultural translation from a European source to be out of context in Iranian society, and thus, partially or fully incomprehensible. In this research, I will ask how the main approaches of the twentieth century Iranian intellectuals to Western modernity can be understood with theories of translation—specifically the triple schemes of translation: word-by-word, sense-for-sense, and transposition— and how these approaches compares with relevant thoughts by both the postcolonial theorist Frantz Fanon and also by Frankfurt School critics, such as Walter Benjamin. Furthermore, this project explores the popular representations of the dandy as an agent of Eurocentrism and an out of tune translation in the context of Iran’s social history. Several twentieth century intellectuals described those individuals estranged from Iranian culture and familiar with European cultures and languages as dandies. The dandy came to be representative of the embodiment of alienation. I argue, dandies were perceived by their critics as performing a translation (or a copy) of European people in Iranian society without making much sense in the target society and culture of Iran. I ask what understanding of cultural translation was the basis of the critiques of the twentieth-century intellectuals who mocked dandies for being a translation (or copy) of European people in their anticolonial gestures, and how their critiques relate to prevailing colonial and anticolonial discourses. By investigating twentieth century literature and political thought the project explains the circumstances under which intellectuals considered cultural translation an enrichment of culture, and those in which they considered it a condition for alienation. The project explores the role of gender norms in shaping intellectuals’ social discontent, and the ways in which social anxiety over effeminacy in the modern era led some intellectuals to fear for the future of the nation.