This dissertation examines how the Venetian Renaissance artist Titian Vecellio used one of his last paintings, the Flaying of Marsyas, as a holistic visualization of his artistic legacy. The mythological tale, derived from Ovid’s Metamorphoses, chronicles the fateful competition between the hubristic satyr Marsyas and the god and protector of the arts, Apollo. The myth has often been read as a contest between the divine and earthly realms of art and was thus used in the Renaissance as an analog to the paragone, or competition of the arts—especially between painting and poetry and painting and sculpture. In Titian’s rendition of the scene, the brutal flaying becomes an allegory of the creative process, and of the rivalry between Tuscan disegno, represented by Michelangelo, and Venetian colore, embodied by Titian. The myth’s personal resonance is more intimate by the inclusion of the aging painter’s portrait in the guise of the foolish King Midas. This dissertation recontextualizes Titian’s Flaying of Marsyas as a final portrait ‘in malo,’ in which the painter embraces figures associated with vice. Beginning in 1516 until his death in 1576, Titian produced at least six disguised self-portraits of this type that satirically addressed his public reputation and legacy. At the end of his life, reflecting on his accomplishments and public perception, Titian’s portrait as Midas becomes the culmination of Titian’s artistic paragone, emblemizing his rivalry with Michelangelo, poetry, and himself.