This work examines the ways in which the culture and society of the Middle Ages impacted on the works of the Sienese poet, Cecco Angiolieri (c.1260-1312). It analyzes how Angiolieri's poetry conformed to medieval notions and practices of comicality. The study explores the means by which Cecco satirized important cultural movements of the late 13th and early 14th centuries, such as love literature and the ascendant Franciscan order. In addition, it looks at his relations with other writers of the day, including three insulting sonnets addressed to Dante Alighieri. The text shows that Angiolieri was not an isolated, "bizarre" figure, as some early 20th century scholars have described him, but rather an author in step with his times.