This paper explores Walter Benjamin’s relationship with French Surrealism from sources rarely studied or practically unknown until now. First, I will set out the direct link between the theses on “profane illumination” and the “organization of pessimism” in Der Sürrealismus. Die letzte Momentaufnahme der europäischen Intelligenz, and various texts by Pierre Naville, one of the most active figures in the Surrealist movement between 1925 and 1929. Second, I will consider Benjamin’s commentaries in Pariser Passagen and convolute “S” of the Passagen-Werk about Surrealist writings and Martin Heidegger’s Sein und Zeit, flagging up the implications of this confrontation for Benjamin’s ideas of secularization of mysticism and messianism. Lastly, I will seek to refine the meaning of Benjamin’s “anthropological materialism” and its relevance to those sections of the Passagenarbeit that are dedicated to the evolution of social movements since the French Revolution.