In the German-speaking countries during the morally uninhibited years of the Weimar Republic, the opposing cultural epochs of Expressionism and Neue Sachlichkeit dominated the aesthetic landscape. Opera was a central proponent of both movements, as implemented by the Expressionist practitioners and those who favored the subsequent topical and objectifying Zeitoper that sought to move away from representations of psychological distortion to depict social realism that emphasized mechanical technology and lighter, popular narrative themes. Max Brand’s famous Zeitoper, Maschinist Hopkins, will be analyzed to illustrate how it bore fundamental trace elements back to Alban Berg’s Expressionist opera Wozzeck, and likewise, how Hopkins in turn influenced Berg’s second opera Lulu, to constitute a linear association of narrative, music, and theatrical design that simultaneously conformed to and defied the operatic models that all three operas are historically associated with. It will also be suggested that both composers were consequentially influenced by Richard Wagner, promoting vestiges of an even older lineage, which contributed to this association between the three operas at a time when Wagner was less applicable to the trends of innovation and progress.