This chapter examines the role of edutainment within the Brother2Brother programme, specifically focusing on the radio drama series Brother2Brother and three short films: Mwamuna Atani? (What Should a Man Do?), Bongani (Give thanks) and Ungwiro (Virtue). Created by the participants and disseminated to secondary school and college students, these creative productions addressed core themes explored in earlier arts-based workshops. The chapter begins by outlining the ideological framework and methodological approach that informed Brother2Brother’s edutainment initiatives. Part I examines the creative process behind the radio dramas and their thematic content; using three episodes and their reception in three schools, I illustrate how pupils were empowered to interrogate gender, peer pressure, sexuality and teenage pregnancies. Part II analyses the production and reception of the short films, using post-screening discussions in two colleges to demonstrate how film-stimulated dialogue on gender norms and sexual harassment. Ultimately, the chapter argues that participatory edutainment can enable young people to challenge rigid gender norms and explore transformative social change.