Teaching the “Film and History” unit at Clemente Ballarat involved an intersection of two different models for traversing boundaries of traditional education. Whereas Clemente extends academic learning beyond education institutions to a community setting, film and history is a study area that brings together the realms of screen entertainment and historical scholarship. Focusing on historical films, the Film and History unit involved encounters with “histotainment”, the merging of creative representation with depictions of the past. While studying history on screen can serve a basic instrumental purpose of rendering past events accessible, the Film and History students contributed to generating discourse about a wide range of themes that extended beyond specific learning goals. The richest class discussions often seemed to be shaped by students’ own perspectives as people with complex life experiences. They raised questions about what a historical film is; how historical films relate to the present day; collective and individual histories; and identity and agency. This chapter outlines debates and reflections that arose in the unit, with a focus on selected examples of topics that were studied, and the potential uses of these ideas for transformative education programs and lifelong learning.