Figures who turn their heads frontally and gaze outwards from Archaic Greek artworks look back at the viewer and destabilize the typical relationship between viewing subject and viewed object. These frontal characters were especially effective for viewers who encountered them during the Archaic period, when the profile perspective was conventional and vision was understood to be a tactile sense. Frontal-facing figures have often been interpreted as carrying protective power or having the ability to threaten the viewer with their attention. While some frontal figures are intimidating, frontality and the represented gazes it engenders do not provoke a single, universal reaction. Instead, these images’ interactions with ancient viewers were shaped by the type of frontal figure represented, the figure’s representational context, and the real context in which the figure was originally encountered. This dissertation takes a contextual approach to the study of Archaic frontal figures to arrive at a more nuanced understanding of their functions and effects. The frontal figures that are represented on vases made between 700 and 480 BCE are comprehensively examined. Frontal-facing characters that decorated temples in the same period are also considered. By inspecting each individual type of frontal figure in turn, we can better comprehend the differing responses the figures elicit, which include humor and horror in addition to terror. This project also examines how frontality was employed by innovative vase painters to create images that directly engage viewers and shape their viewing experiences. While a few figures were conventionally frontal in the Archaic period, the majority were represented frontally only by the most experimental artisans who were eager to surprise their viewers and distinguish their work from that of their colleagues. This investigation of Archaic frontality in multiple media demonstrates the power of the perspective in its original context and the inventiveness of the craftsmen who used it.