It may come as no surprise to find shared images in the lofty philosophical, medical, or astronomical musings of the Romans and the Arabs; as is well known, both of their traditions drew from the same ancient Mediterranean sources, and especially from the Greeks. It is more difficult to explain the striking resemblances between some lowlier, more earthy images of Roman and medieval Arabic literature, such as those found in association with the humble person of the donkey. This paper will focus especially on stories about donkeys and humans interacting, stories about people imitating the voices of donkeys, and on stories about people having sex with donkeys. In exploring how these stories play on philosophical conceptions of man-as-microcosm on one hand, and on popular beliefs about the evil eye on the other hand, I will show that the boundaries between elite and popular literature often blurred in both the Roman and the medieval Arabic examples, and that shared features between both suggest hitherto unsuspected regions of shared cultural beliefs of the people of the Roman empire and those of the medieval Islamic empires. My analysis will include the Priapea, Apuleius’s Golden Ass (or Metamorphoses), al-Jahiz’s Kitab al-Hayawan, the epistles of the Ikhwan al-Safa’, Sufi poetry, and prophetic hadith, among other sources. I will conclude by musing on the origins of certain donkey images found in later European literature, and by pondering their similarity to both Roman and Arabic donkey stories, will find the lines between “East” and “West” hopelessly blurred.