In this article we explore the utility but also limitations of gender stereotyping lessons, a common undertaking by teachers introducing media analysis to youth. We document our collaboration with a Canadian high school teacher as she translated her understanding of critical media literacy into practice in a unit addressing questions about the gendered nature of pop music videos. Informed by feminist cultural studies, we explore challenges that arose when teaching about gender stereotyping. Factors that circumscribed deeper inquiry included (a) discussing whether media texts were unrealistic rather than focusing on meaning-making practices; (b) inattention to hidden yet active media texts that worked to sustain dominant meanings; (c) lack of access to counter-frames; (d) inattention to intersectionality so that gender was conflated with sex and sexuality, allowing heteronormativity to go unrecognized; and (e) the ambiguities of how sexual power operates in commercial pop culture, making it difficult for students to discern feminist parody.