“Shock” is perhaps the central concept of modernist aesthetics and Walter Benjamin its best known theorist. It has been well documented that Benjamin’s long-lasting friendship with Bertolt Brecht and the latter’s dramatic theory had a profound influence on his thinking about this notion. Brecht's techniques of interruption and juxtaposition in the practice of epic theater were in close relationship with Benjamin’s use of montage as a mechanism to “liberate” meaning. Despite Theodor Adorno’s and Gershom Scholem’s attempt to situate Benjamin’s thought in a different aesthetic tradition, Brecht’s understanding of Verfremdung (estrangement) and Benjamin’s idea of “shock” are often deemed identical. In this paper I compare both concepts, looking at their points of coincidence and tension. I also relate their development to one of the most telling friendships in the history of twentieth-century philosophy.