This paper examines the aesthetics of Yusuf al-Shirbini’s (d. after 1686 CE) Hazz al-quhuf bi-sharh qasid Abi Shaduf in relation to its social, cultural, and historical contexts. As an Arabic text from Ottoman Egypt in the 17th century, it was produced during the period that modern thinkers labeled ‘asr al-inhitat (period of decadence/decline/decay). Although recent scholarship has deconstructed the assertion that there indeed was a period of cultural decline between the 13th and 18th centuries CE, this scholarship has often focused on the rhetoric of decline—classifying it as Orientalist—rather than considering the cultural production of this so-called decadent period. As such, this paper seeks to bridge this gap by paying attention to the aesthetic qualities of Hazz al-quhuf, including its use of the colloquial Egyptian and its transgression of various genres. In the first part, drawing on the work of Nelly Hanna, Konrad Hirschler, and Thomas Bauer, this paper attempts to make a connection between the text’s aesthetics and socio-political context. What is the significance of Shirbini’s parodying of the sharh (commentary) genre? What does one make of the text’s focus on peasants as the “protagonists” of this text? What do the text’s intertexts—from Abu Nuwas’s (d. 814 CE) poetry and the 1001 Nights to Ibn Sudun’s poetry (d. 1464 CE) and al-Safadi’s (d. 1363 CE) commentaries—tell us about the text’s purpose and audience? In asking these questions, this paper argues that we must reassess our aesthetic sensibilities and read this text, and others from the same period, on their own terms, and it suggests how we might do so. In the second part, this paper draws on recent scholarship on premodern vernaculars in the Middle East, by Michiel Leezenberg and others, and situates Hazz al-quhuf within the history of this precolonial “vernacular revolution.” How can one assess the aesthetics of the text’s vernacular elements? What does the liberal use of the vernacular in the text tell us about Ottoman Egypt in the seventeenth century? This paper shows that the aesthetic qualities discussed in the first part are reflective of social and political shifts during this early modern period that are only now beginning to be studied by literary and cultural historians. This paper concludes by revisiting the inhitat paradigm in light of the discussion of the text’s aesthetic qualities, as well as its historical, social, and political milieu.