Despite being contemporaries, Walter Benjamin and Martin Heidegger never directly engaged with one another. Yet, Hannah Arendt, who knew both men, pointed out common ground between the two. Both were concerned with the destruction of metaphysics, the development of a new way of reading and understanding literature and art, and the formulation of radical theories about time and history. On the other hand, their life trajectories and political commitments were radically different. In a 1930 letter, Benjamin told a friend that he had been reading Heidegger and that if the two were to engage with one another, "sparks will fly." Acknowledging both their affinities and points of conflict, this volume stages that confrontation, focusing in particular on temporality, Romanticism, and politics in their work.