This article demonstrates how by using J.R.R. Tolkien’s Lord of the Rings (LOTR) as a text in the classroom instructors can relay the international relations (IR) “Great Debates” and feminist “waves” to students through the framework of “where you stand depends on where you sit.” It overviews how J.R.R. Tolkien’s acclaimed trilogy is relevant to learning about IR and then presents a number of “cuts” into using LOTR to inform IR teaching of both problem solving and critical theory. It begins by parsing the three “Great Debates” of IR theory and three “waves” of feminist theory in terms of different worldviews by relating them to characters from the trilogy. Next, the paper suggests that a critical evaluation of this analysis conveys that concerns, goals, and understandings of problems and insecurities are influenced (although not determined) by context, such as gender, race, class, sexuality, and postcolonial position. It concludes by suggesting that further use of popular culture and the humanities can help IR teaching both illustrate and critically reflect on IR scholarship.