Research into leadership often focuses on standard business organizations. We know little about these proposed models apply to leadership in other contexts, such as the military, sports, film and television industries or religious organizations. Here, we deliberately reverse the idea of investigating how standard models fit into non-standard contexts; we want to know what leadership lessons can be drawn from compelling yet understudied contexts. Research and theory from four types of contexts are presented: Those characterized by high levels of competition, such as sport, those in which the generation of innovation and creativity is crucial e.g. film and television, high-risk contexts such as the military and aviation, and those where fostering the well-being of others is at the core. To summarize, as much as we can learn about leadership from standard business organizations and apply it to unusual contexts, the same applies the other way round: Idiosyncrasies of compelling contexts teach us fundamental lessons about leadership which are also applicable to other settings.