Musicians have access to an ever-growing array of technological tools, creating a world rich with new artistic possibilities. Yet the incursion of automation technology into creative pursuits has long sparked panic about the threat to human creativity and authenticity. Relating a 120-year history of automation in music, this book provides a timely historical demonstration of how older technologies of automation gave rise to initial unease, which was then followed by integration and exploration of their generative potentials. Journeying from the player piano at the turn of the twentieth century, through the introduction of drum machines and synthesizers, to the holographic pop stars of the twenty-first century, Alyssa Michaud shows how musical subcultures have shifted the parameters of debate around the meaning of automation and creativity. In riveting prose, Automatic Artistry directly addresses the choices we now face as we adapt to the newest wave of automated musical tools.