This chapter investigates the nature of the well-documented influence of the German playwright, theorist and director Bertolt Brecht on the Syrian playwright Sa’dallah Wannous. In addition to examining theoretical and indirect links between the two, such as Wannous’ interviews and friendships in France with Brechtian theatre artists and scholars such as Jean-Marie Serreau, Jean-Louis Barrault, Peter Weiss and Bernard Dort, this chapter looks at Wannous’ creation of innovative hybrid works that utilized Brechtian dramaturgical techniques alongside traditional Arabic performative modes. The chapter also analyzes manifestations of these re-workings of Brechtian dramaturgical models in performance in two very different stagings, one in former East Germany and the other in the former Soviet Union, of one of Wannous’ most innovative plays, The Adventure of the Head of Mamlouk Jabir. It also highlights Wannous’ participation in the Brecht Dialogue in 1968 in East Berlin, which commemorated the playwright’s seventieth birthday, and the documents and theatrical programs from that event that were recently found in Wannous’ personal library, which is now housed at the American University of Beirut.