As youth media creation programmes proliferate, educators and practitioners are learning how to develop stories that interrupt hegemony and point to new ways of being. This research, carried out in an ethnically diverse middle school, highlights the way digital storytelling as an applied theatre praxis brought complexity to student work. The role of a Media Wish List and students' propositional digital stories have implications for the way educators and practitioners approach digital storytelling with youth, and how applied theatre processes can be leveraged to enhance digital storytelling in classrooms.