The police detectives of Hollywood’s Training Day (2001) and cable television’s The Shield (2002-), Alonzo Harris and Vic Mackey, represent the newest face of evil in entertainment media. Harris and Mackey are menacing, rough cops who rule their urban beats like the street gangs and criminals who co-exist in the same cement terrain. TrainingDay and The Shield utilise a discourse that emphasises racial signifiers and class positioning to portray a social environment that justifies the presence of such troublesome policing. Through a critical, cultural analysis of these figures, we explore these sociopolitical themes while expounding upon definitions of evil that begin with describing a war between light and dark, black and white. Our analysis is informed by James McDaniel, St. Augustine, and Nietzsche’s definitions of evil. We argue that, by definition, only the Alonzo Harris characterisation, portrayed by a Black body, in contrast with that of a white Vic Mackey, can be considered truly evil in nature by virtue of his undivided emersion in the “dark” - morally and racially.