During his time as a young artist in Munich (1917–1924), Brecht’s burgeoning approach to drama and theater was considerably influenced by the playwright and cabaret performer Frank Wedekind and the Bavarian comedian Karl Valentin. This chapter outlines the nature of Brecht’s contact with these two artists and their performance work, and demonstrates how their aesthetic approaches had a significant impact on the development of his epic theater. In particular, it attends to how both artists provided compelling strategies for defamiliarizing material realities and societal oppression. While Wedekind offered enthrallingly deviant protagonists and repurposed popular art forms – cabaret, circus and the Moritat, Valentin’s clowning and fairground style inducted Brecht in the deployment of gestic performance and comic incongruity. What the chapter makes apparent is the extent to which these artists provided Brecht with key models for a subversive theater that recycled old and new, popular and highbrow forms in order to deliver a social commentary that was richly satirical and fun.