In seventy-four couplets, the famous Anatolian poet Sheykhi (d.1431) composed a poem, Harname (The Story of the Donkey), narrating the story of a donkey that, after seeing the oxen comfortably grazing in the meadow while he was under the burden of carrying a heavy load, aspires to change the conditions in which it lives. Found by its master resting on the fields that he ruined, the donkey is punished by its master who beats it and cuts off its ears and tail. Sheykhi presented this poem to his patron, the Ottoman sultan Murad II. This story, commonly considered comic, violent, and unusual, is at the same time referred as the example par excellence of Ottoman satire. However, there are many questions with regards to its reception: Why would a renowned poet present such an uncommon poem to the sultan? How did this short and unusual literary work acquired an uninterrupted acknowledgement by readers and scholars at the same time? Already in the sixteenth century Ottoman biographical dictionaries of poets regarded Sheykhi as the founder of Anatolian lyric poetry and attempted to explain the rationale behind his unusual composition. Yet, the answers given in these biographical dictionaries differ considerably from each other. In this paper I argue that different and at times contradictory evaluations of Sheykhi's controversial poem signifies diverging forms of interpretation produced by vested interests of the sixteenth century Ottoman biographers. This paper first presents a brief account of the poem, its composition, language, and imagery. Then it considers and evaluates how the three most renowned Ottoman biographical dictionaries explained the imagery and plot of the Harname in relation to Sheykhi's life story. Finally, I propose a new methodology to study the sixteenth century Ottoman literary critical tradition through a detailed analysis of controversies developed around an unusual fifteenth century work of literature.