My dissertation explores the possibilities of depicting difficult history on film by investigating a series of movies and television programs about the Wannsee Conference, which took place in Berlin on 20 January 1942 and was intended to coordinate the Final Solution by asserting the dominance of Heydrich and the SS over other governmental departments. The surviving Wannsee Protocol stands as one of the most compelling pieces of evidence for the Third Reich’s genocidal intent and emblematic of its shift from mass shootings in the occupied East to industrial-scale murder. This dissertation will explore the differing ways in which the difficult German past has been depicted by both German and American filmmakers. Detailed analyses of the HBO/BBC co-production Conspiracy (2001) and the ORF/Bayerischer Rundfunk production Die Wannseekonferenz (1984) form the core of my dissertation. Both films reenact the Wannsee Conference in real time (ca. 90 minutes) and are examples of two approaches to historical filmmaking that reflect differences in both nationalities, television industries, and respective historiographical trends of their times (mid-1980s versus turn of the millennium). This dissertation goes beyond mere film analysis and is grounded in archival research on the production history of both films, which include script drafts, production notes, meeting minutes, and correspondence. Additional oral history interviews with the writers and production staff supplement-but by no means replace-the archival material. Additionally, this project will analyze other, more minor depictions of the Wannsee Conference on film, such as the NBC miniseries Holocaust (1978) and the recent HHhH (2017). In short, the project explores the myriad ways in which American and German filmmakers have attempted to teach the Holocaust via a singular, notorious event while also grounding each attempt in their respective national and historical contexts. In using the Wannsee films as a case study, this dissertation seeks to examine how filmmakers depict history on film and how and why this is important for historians and educators.