Abstract
This chapter analyzes the differences, similarities, tensions, and intersections between two of the most important thinkers of the twentieth century: Walter Benjamin and Martin Heidegger. Given the absence of a real engagement between these two figures, philosophy’s role is to explore both, the possible and the impossible syntheses and antitheses, reassembling them into a constellation, to put it with Benjamin. To arrive at this constellation, philosophy must first clarify some premises, concepts, and tropes on which each thinking relies. The turns offered in this chapter aim to provide a reading between the lines of two conflicting intellectual traditions, represented by Walter Benjamin and Martin Heidegger. By focusing on the history of ideas in general and the tradition of skepticism in particular, as well as on the terminologies each thinker employed, the chapter explores the intellectual terrain between their movements of thought. It finally also addresses the implicit political and ethical questions embedded in their works, traversing the space where these ideas either intersect or repel each other.