Some of the world’s most exquisite medieval paintings, from late fifteenth-century Herat and the early Safavid workshops, illustrate well-known episodes of popular romances––like Leyla & Majnun––that give prominence to depictions of unrelated figures such as a milkmaid or a spinner at the scene of the hero Majnun’s death. This interdisciplinary study aims to uncover the significance of this enigmatic, century-long trend from its genesis at the Timurid court to its continued development into the Safavid era. The analysis of iconography in several luxury manuscript paintings within the context of contemporary cultural trends, especially the ubiquitous mystical and messianic movements in the post-Mongol Turco-Persian world, reveals the meaning of many of these obscure figures and scenes and links this extraordinary innovation in the iconography of Persian painting to one of the most significant events in the history of Islam: the takeover of Iran by the Safavids in 1501. The apparently inscrutable figures, which initially appeared in illustrations of didactic Sufi narrative poetry, allude to metaphors and verbal expressions of Sufi discourse going back to the twelfth century. These “emblematic” figure-types served to emphasize the moral lessons of the narrative subject of the illustrated text by deploying familiar tropes from an intertextual Sufi literary discourse conveyed through verses by poets like Rumi, Attar and Jami, and ended up complementing and expressing Safavid political power at its greatest extent: the conversion of Iran to Shiism.