This chapter provides a framework for understanding teachers as heroes, and also to draw attention to impediments of heroism that can create a villainous teacher. By exploring both misunderstanding and misuse of the power of the teacher role, my goal is to offer a cogent analysis of how teachers can commit subtle acts of passive or active evil. I will use examples drawn from both cultural elements of media such as movies and books as well as cases from news stories and blogs of everyday heroic and villainous teachers. Lastly, this chapter will explore historical role that teachers have played according to social and anthropological analysis connecting the teacher archetype to the Jungian ideals and the study of the mentor to revisit the iconic teachers of Star Wars.