In this chapter, we analyze how players of a tabletop roleplaying game on an actual play podcast make visible the hidden curriculum of schooling and engage in speculative reimaginings of education. Using discourse analysis, we attend to how players improvise characters based on game-provided archetypes, negotiate rules, and build shared worlds, tracing how these practices surface taken-for-granted assumptions about power and discipline. We also consider how the tools of the podcast medium (editing, narration, and sound design) shape meanings that circulate beyond the game table. Situating our analysis within postdigital theories, we highlight how role-playing games and their mediated forms enact gaming literacies that differ from, and productively critique, dominant narratives of teaching and learning. Our contribution shows how collaborative worldbuilding and speculative storytelling can offer humanizing alternatives to mechanized models of education. We conclude by considering implications for designing playful, critical, and inclusive pedagogical spaces.