The ancient Greeks possessed a mythology that was populated by monsters who functioned as signifiers of some of their most closely held anxieties. Monstrosity is used here as a way to access the incorporeal culture of the ancient Greeks. The positioning of monsters as part of a collective tradition meant that they existed in, and impacted, every level of culture, anywhere that stories were told. The main purpose of this Thesis is to explore the ways in which the ancient Greeks represented monsters within their art and literature, from the archaic age to the Hellenistic period, as expressions of their anxieties and fears, particularly relating to gender. The monsters examined range along a mythical chronology, from the primordial era to a heroic age. Primordial monsters, it will be argued, existed as expressions of a feminine tainted chaos, designed in opposition to the masculine rationality of the Olympian order. They were an imagined challenge to a cosmological system that was the conceptual basis for the ordering of ancient Greek human society. The monsters of the heroic age, however, related to the human in even more obvious ways. Heroic-era female monsters were constructed using a series of closely related chthonic concepts, which cast them as aberrant and polluted. The traits used to create these feminine monsters it will be argued were reflections of the Greek understanding of the feminine as 'other'. In contrast the heroic-era masculine will be shown to be the most innocuous discussed. They, like the feminine are reflective of an 'other,' but this 'other' was the barbarian or Wildman; both of which possessed a greater conceptual distance from the male subject than the female within his home. Ultimately, it will be demonstrated that monsters offer a useful avenue into the anxiety-provoking issues of ancient Greek culture and the perceptions of gender that so often fuelled them.