This article applies the critical media concept of organic representation to leadership studies as an analytic of how various creators in popular culture today are not just writing inclusive storytelling but, more notably, modeling new modes of production and self-presentation that are actively challenging hegemonic industry practices and larger cultural ideologies around power, equity, leadership, and success. In conversation with leadership for liberation (see Patterson-Stephens et al. in this issue), I employ an interdisciplinary approach that bridges critical leadership models with critical media analysis to place their aligned perspectives in direct conversation with one another. In pursuant of adding critical media analysis to the leadership studies toolkit, this article applies organic representation to an original analysis of the television series Reservation Dogs and advocates for a critical interrogation of media storytelling, production, and distribution to better understand represented communities also as stakeholders in pop culture narratives.