In contrast to the transcendent image eliding idolatry through immateriality or dematerialization, the transgressive image courts sin to transcend the self. Through the Abrahamic story of the prophet Joseph and Zuleikha, transformed from Judaic and Islamic exegesis to poetry and painting, Chapter 8 explores the trope of the transgressive image. Development of the story from the Talmud into the Bible and subsequent interplay between Jewish and Islamic commentaries suggests close interreligious communication. The story’s fifteenth-century romantic popularization in Persian poetry, first by Sa’di and then by Jami, used tropes of dreams and idols to transform the story into a parable describing the path to divine union. Combining text with image, Bihzad’s famous rendition of the climactic scene responds to the poem’s intermediality. Comparison with the transgressive dream vision central to the tale of Shaykh Sam’an in Attar’s Language of the Birds underscores a broader recognition of idolatrous transgression as a path to salvation. The chapter concludes by contrasting the mystical, humanizing interpretation embodied in these tales with depictions of the same romance in Europe. Recognizing the independence of European painting from text as an inappropriate paradigm for manuscript paintings embedded in texts, the chapter suggests the need for contextual critical reading of poetry through theology as well as politics to ascribe visual meaning.