Arnold Schoenberg and Sigmund Freud were contemporaries, and were at the forefront of artistic-aesthetic and intellectual-scientific revolutions in early twentieth century Vienna. This essay argues that there are many striking parallels between these two iconic Viennese figures, and that their lasting influence and legacies can be profitably viewed and understood in light of this parallelism. This essay explores the lives and careers of Schoenberg and Freud, comparing their personal histories, the development of their respective theories and methodologies, their views towards disciples and apostates, and their attitudes towards priority.