One of the twentieth century’s most significant artists, Cindy Sherman has quietly uprooted conventional understandings of portraiture and art, questioning everything from identity to feminism. Critics around the world have taken Sherman’s photographs and extensively examined what lies underneath. However, little critical ink has been spilled on Sherman’s only film, Office Killer, a piece that plays a significant role both in Sherman’s body of work and in American art in the late twentieth century. Dahlia Schweitzer breaks the silence with her trenchant analysis of Office Killer and explores the film on a variety of levels, combating head-on the art world’s reluctance to discuss the movie and arguing instead that it is only through a close reading of the film that we can begin to appreciate the messages underlying all of Sherman’s work.