This article considers how new materialist, Indigenous and posthuman feminist theories might be applied to drama pedagogy and research to empower young people to play "within" the trouble of colonial legacies and heightened climate crises. It references an Australian school project that used Heathcote's Rolling Role system of teaching (1993) as an imaginative and transdisciplinary climate activist pedagogy, framing young people inside the entangled 'trouble' of our times, so they can 'make oddkin' with critters needing care, protection, and sanctuary. Using a critical autoethnographic approach, this article considers how drama can work on/within the ethical imagination in tentacular ways.