In an online graduate-level early childhood education course, the authors sought to playfully disrupt and transform educators’ conceptions of children’s “dark play,” as provoked by contemporary popular culture. Embracing the imaginative potential of darkness and liminality, the course participants problematized and expanded their thinking concerning what constitutes children’s play scripts focused on themes of fear, power, and violence. Cognizant that some educators are reluctant and even refuse to allow children opportunities to engage in play centered on troubling social issues, the educators co-authored a fantastical tale, inspired by the Disney animation film Frozen, and included course topics, classroom observations, and their own childhood memories of “dark play.” Vivian Paley’s ideas about the connections between storytelling and play provided a creative impetus to the fictional narrative-imagining exercise, as did Hans-Georg Gadamer’s notion of Spiel. Eliciting the literature of children’s play experiences through fictional story-writing, and “play” as a contemporary aspect of creative thinking, the educators entered imaginary worlds of their own making. Unlike a traditional online graduate course format that often incorporates textual readings, posts, and responses, the authors strived to foster a virtual space in which the educators buttressed theories about play and imagination in a deeply felt, experiential, and playful manner. In creating an imaginary story based on the film, the participants gained a different understanding of the nature of play, and came to recognize how popular-culture play themes can provoke and strengthen children’s imaginative and abstract thinking, problem-solving skills, and emotional development. Likewise, this narrative experience showed the potential and role of “dark play” in initiating new ways of thinking and talking with children about the complex issues of the modern world.