Few subjects have excited the imagination of archaeologists working in ancient complex societies as have monumentality and urban planning. Yet the two topics are rarely explicitly theorized in a sustained integrated investigation within a single study, despite the fact that monumental architecture is often considered a primary basis for identifying the presence of urban planning. This article makes the related methodological arguments that both phenomena benefit from a more full consideration of one another, and that the meaningful aspect of monumentality and urban symbology needs to be considered in conjunction with the formal aspect of monuments and urban layouts. These positions are then implemented in a study of the Syro-Anatolian city-state system that existed in the ancient Near East during the early first millennium bc. The capital cities of these polities were characterized by a program of monumentality that brought royalty, city walls, gates and monumental sculpture into an unmistakable constellation of associations. The consistency of this pattern of monumentality and urban form suggests that at least a degree of urban planning existed.