Historical depictions of angels are a suitable means of tracing transculturality in the ancient world. For more than four centuries, and as far as the end of late antiquity, two great world powers, the Sasanian Empire, the last pre-Islamic Persian empire, and its neighbor, the Roman Empire, ruled the Near East and the Mediterranean—sometimes as well-disposed partners and, sometimes as rivals. Choosing Zoroastrianism as the empire-wide religion, Sasanians developed and complemented their in-house religious iconographic canon. The Sasanian canon contains some iconographical elements borrowed from previous or neighboring cultures, which the Sasanian artists translated, alongside their own creations and “iranianized” in a proper Zoroastrian mode. The cultural legacy of the Sasanians in turn became a great source of inspiration for medieval art and architecture both in Europe and Asia. In this article, significant examples from the religious canon of Sasanian iconography are studied in reference to the cross-cultural entanglements of angels.