Andy Warhol, a flamboyant character among Modern artists of the time, is known for the infamous Campbell’s Soup Can along with the Cow Wallpaper. Yet, while exposing audiences to commercialism and consumerism through his works, he also approached social and cultural events and fads during the time period in which Modernism reigned. Warhol’s Five Deaths Seventeen Times in Black and White, a part of his Disasters series, focuses on the infatuation with tragedy among celebrities. However, upon closer investigation, theories of Formalism and Postmodern Pluralism reveal a hidden undertone. Though the work is impactful to the viewer at first glance, one must become actively engaged to truly understand the complexity that is Five Deaths Seventeen Times in Black and White. In a discussion-based presentation, I will reveal the undertone while discussing the cultural context and history of tragedy and Modernism as well as theories relevant to this piece.