The notion of 'Sociomateriality' has recently gained in popularity among information systems (IS) scholars in their search for providing new ways of investigating and theorizing about IS in organizations and society at large. While some scholars put forward arguments and research accounts that lead to new insights, others expose a cursory treatment and partial appreciation of the idea. In addition, sociomateriality as a new worldview has been criticized for introducing yet more academic jargon monoxide. Although existing research and debates show some potential for progressing the theorizing of 'man-machine' reconfigurations, we point to the necessity of a deeper exploration of the term. Inspired by the call for papers of the Alternative Genres Track at ECIS 2012, the purpose is to take a fresh look, to evoke new insights and to gain deeper understanding of the notion of sociomateriality in IS. Towards this aim, the reader is invited to attend a prolonged monologue characterized by honesty, frank observations and wit delivered by the court jester and directed to the sovereigns based on their writings. The intention is to contribute with a stimulating recital that builds on open-minded questions in the pursuit of key reflections to inform our research discipline.