My dissertation studies the typological juxtaposition and syncretic incorporation of classical and Christian elements—subjects, motifs, and forms—in the art of the Italian Renaissance and the significant meaning of classical subjects and figures in such contexts. In this study, I analyze the interpretative modes applied to extra-Biblical and secular literature in the Italian Tre- and Quattrocento and the syncretic philosophies of the later Quattro- and early Cinquecento and reevaluate selected works of art from the Italian Renaissance in light of the period claims and beliefs that are evident from such a study. In summary, my dissertation considers the use of classical subjects, motifs, and forms in the art of the Italian Renaissance as a means to gloss or reveal aspects of Christian doctrine. In chapter 1, I respond to the paradigm proposed by Erwin Panofsky (Renaissance and Renascences) and establish a new criteria for understanding the difference between medieval and Renaissance perceptions of classical antiquity. Chapter 2 includes a study of the mythological scenes painted in the Cappella Nova of Orvieto Cathedral, which are here shown to gloss and reveal aspects of the developing Christian doctrine of Purgatory. In chapter 3, I study the Renaissance use of representational ambiguity as a means of signifying the propriety of pursuing an allegorical interpretation of a work and specifically address the typological significance of figures in Botticelli's Primavera. In chapter 4, I examine the philosophical concepts of prisci theologii and theologicae poetae and their significance in relation to the representation of classical figures in medieval and Renaissance works of art. This study provides the necessary background for a reevaluation of syncretic themes in Raphael's Stanza della Segnatura, which is the subject of the final chapter. In chapter 5, I identify classical figures in the frescoes of the Stanza della Segnatura—among them, Orpheus in the Parnassus and Plato and Aristotle in the Disputa—and offer a new interpretation of the iconographic program of the Stanza della Segnatura frescoes as a representation of the means by which participants in the Christian tradition, broadly conceived, approach God through the parallel paths of dialectic and moral philosophy.