Philosophical hermeneutics has much to offer the high school English teacher, for it fundamentally reorients our understanding of what it means to interpret – or teach (with) – literature. When we adopt a hermeneutic stance, we begin to see literature as a formative space. It is in this space, I contend, that we may begin to reorient attitudes towards what and why we read. The following research, therefore, is my attempt to come to know the hermeneutic tradition, and the manner in which its principles and practices have been taken up by scholars in the various fields of literary cognitivism, arts-based pedagogy, and curriculum studies. In this way, I endeavor to better understand the manner in which we think about teaching literature in schools. Ultimately, I examine what a hermeneutic ethos looks like within the context of a literature classroom and how it might inform a coherent approach to teaching (with) literature.