My dissertation considers the changing dynamics between Michelangelo Buonarroti’s artistic practice and poetic development. It centers on the two decades after his move to Rome from Florence in 1534, which was a catalyst for his production of hundreds of poems and private artistic projects simultaneous with his papal commissions. My project provides a comprehensive examination of the parallels in style, form, genre, and textual sources of Michelangelo’s art and poetry of this period, especially in relation to Italy’s varied literary landscape. It will thereby shed light on the burgeoning vernacular culture in Rome after the sack of 1527. I will chart Michelangelo’s relationships with a new generation of intellectuals who participated in polemics on topics such as poetic imitation and the development of the Italian language. By studying archival sources, rare books, and art objects, my dissertation will show how Michelangelo’s visual production reveals his engagement with a wider literary discourse.