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Scholars have often conceptualized premodern theater as a socially equalizing medium through which the lower proletarian classes may voice their opinions and concerns via humor and political satire. A famous example is Pierre Gringore’s Sottie du Prince des Sotz et Mère Sotte (Play of the Prince of Fools), which features both the king and the pope as fools. As Cynthia J. Brown’s The Shaping of History and Poetry in Late Medieval France: Propaganda and Artistic Expression in the Works of the Rhétoriqueurs has demonstrated, comic theater of the sixteenth century often functions to temporarily reveal “the joyful relativity of all structure and order.” In this study I show the Intronati Academy of Siena harnessing the power of theater to similar ends. However, rather than representing the relativity of social structure and class order, their plays elevated comedy and studies of humanism more generally to a noble position in the city of Siena during the century. I consider the Intronati’s L’Amor Costante, written for the entrance of the Holy Roman emperor, Charles V, into Siena in 1536, and L’Ortensio, composed for the entrance of Grand Duke Cosimo I de’ Medici in 1561, in light of their relevant paratexts to show that the Intronati not only used theater to give a voice to the citizens of the city but also employed comedy in entrance festivities to negotiate the power of the academy over the people.