This chapter surveys art history, patristic theology, and modern Orthodox theology to identify a starting point that can address the mediating function of the icon. However, each of these approaches is also marked by limitations that ultimately leave them unable to sufficiently address two questions that are essential to this inquiry: (a) What is a painted image, and how does it mediate the truth of what it shows by its specific, finite capacities and aesthetic devices? (b) What would it mean for God to “show himself,” or what kind of “visibility” would God have? I make a case that phenomenology will be a powerful tool to address both questions.