This paper addresses how the structure of cabaret was translated into painting by the artists of the Weimar era. German cabaret was a theatrical art form that actively welcomed visual artists into its domain. In turn, German artists responded to their shared strategies of art making, recognizing their common bond of Nietzsche’s aesthetic and existential philosophy. Both shared progressive, leftist political concerns, solidifying their reciprocal interests and mutual concerns. Also, the cabaret environment provided artists with a setting in which to explore the social and psychological manifestations found in their culture, and to find inspiration from its dazzling array of types. Both cabaret’s text and performances were directed towards an audience representing a microcosm of its society, and this was understood by visual artists who adapted cabaret’s course of action and common targets. This in turn provided artists with a method to transform the language of images into a critique expressed within their own works. And this environment of cabaret’s conceptual palette of human behavioral types and performance structures, mixed with the artists’ social and historical conditions, together with their readings of the works of Nietzsche and Wagnerian Gesamtkunstwerk, resulted in the creation of intermedial works of art. Such works differed from the era’s New Objectivity style that was characterized by a lack of emotional content, in including cabaret’s spectacle of amusement and heightened emotional levity to emphasize the extreme social disparities and injustices of their time.