This essay explores how the films Becket (1964) and The Lion in Winter (1968), both starring Peter O’Toole as Henry II, can start conversations about medieval sexuality, politics, and religion in the undergraduate classroom. All three of these topics are frequently imagined by students as monolithic in the medieval period; sex and sexuality, for example, can be reduced to heterosexual practices joylessly regulated by church law. Insofar as students have a conception of medieval political systems, these are usually imagined as both strictly hierarchical and inescapably oppressive. Medieval religion — usually Christianity — is also often imagined as an instrument of oppression and control. All these negative assumptions can be productively interrogated using these films. This essay explores how the films — colorful, tightly scripted, and featuring arguably some of the twentieth century’s most celebrated actors — are useful teaching tools, both in an undergraduate course on the Middle Ages in cinema, and in a general medieval survey course. Becket, with its characteristically Anouilhian theme of realism vs. idealism, is a good starting point for discussing the complexities of medieval law, church politics and the church’s social functions with students. The films also help to start useful conversations on the visibility and invisibility of medieval women in film. Finally, both films depict queer sexualities in ways that are at odds with much popular medievalism. Whether in The Lion in Winter’s multiple transgressive sexual relationships, or in the visually explicit erotic tension between Burton’s portrayal of Becket and O’Toole’s Henry II, this essay examines how these films challenge students’ preconceptions and create opportunities for analyzing relevant primary sources. As such, this essay discusses both pedagogical strategies and assignment options related to the two films. I argue that both films can encourage analysis of the Angevin Empire and its afterlives in popular culture, and that this analysis is broadly relevant to popular medievalisms.Banner image: The Lion in Winter (1968), Haworth Productions. Image taken from Filmdetail (www.filmdetail.com).