I center my analysis on Amazon’s recent foray into alternative history The Man in the High Castle premised on Philip K. Dick’s 1962 novel of the same name. Amazon Studio’s production The Man in the High Castle builds upon the premise of an alternative history where World War II ends differently. Here, the diegetic narrative depicts a United States split into three distinct regions: the east coast, now part of the German Reich; the Neutral Zone, or most of the Midwest and the Rocky Mountains; and the west coast, controlled by Japanese Empire. The film version debuted in 2015 as a series extending to four seasons of 10 episodes a piece by 2019. I argue that the show takes cues from modern political tensions, the rise of the alt-right and “post-truth” media manipulations, to intentionally destabilize viewers’ memories of the historical past. By blurring the boundaries between the diegetic reality of the show and our accepted version of history, The Man in the High Castle disrupts the facility in which the viewer assumes alignment with memory and past, opting instead for a complicated refiguring of the political present. Here I articulate how film as a medium tampers with the viewer’s ontological understanding of image by collapsing history and fiction together. Additionally, the capacity of film to provoke empathy from viewers complicates the universal condemnation of Nazism we are familiar with and permits viewers to see the banality of evil in this reimagined history. Finally, I discuss how film as a medium capitalizes on the incompleteness of memory and the loopholes of history to fabricate viewer memory.