North American children are growing up in a media-saturated landscape. Since the deregulation of children’s television in the 1980s in the United States, an explosion of intertextual transmedia franchises has resulted in Canadian children being surrounded by not only film and television texts, but also by media-based toys and merchandise. Market segmentation means these toys and related items are highly gendered, with themes that include femininity, passivity, appearance and friendship for girls, and hegemonic masculine ideals including dominance, aggression, militarism and competitiveness for boys. This investigation undertakes an observation of children at a daycare and a preschool, in Montreal, engaged in pretend play utilizing media-based toys and dress-up costumes to understand what types of gender discourses circulate through play with these items. Results indicate that the gendered themes evident in the media-based toys and narratives are taken up by the children and become part of their everyday play worlds, exacerbating gender policing among peers. However, aspects of gender discourses are also contested as some children take pleasure in subverting gender norms, or turning submissive roles into more agentic positions in play. The production history and content of some of the media-based franchises are also examined, as well as pedagogical approaches that may prevent critiques of hegemonic gender discourses in the early childhood education environment.