During the late-second to first century BCE, Tigranes II the Great of Armenia (140-55 BCE), Antiochos I Theos of Commagene (ca. 86-38 BCE), and Mithridates VI Eupator of Pontus (134-63 BCE) employed multivalent imagery to legitimize their positions and assert their authority amid the changing political landscape of the Hellenistic East. Each king's visual program shaped and reflected the political dynamics of his reign, the mixed cultural identity of his population, and the threats posed by foreign powers. As the kings negotiated their positions within an environment rife with military conflict and in territories composed of multi-ethnic populations, they created nuanced visual programs that layered ties to multiple historic precedents and religious authorities. Each king's program intended to communicate differently to diverse audiences - both foreign and domestic - while simultaneously asserting the king's position as the ruler of a powerful and unified realm. This dissertation considers the rulers' creation and dissemination of such imagery, revealing new dimensions of ruling ideologies and visual culture in the Late Hellenistic East.