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This dissertation provides the first comprehensive study of the artistic production of the Spanish composer, poet, and playwright Juan del Encina (c. 1468–1529). Focusing on the first edition of his Cancionero (Salamanca, 1496)—a work regarded as a landmark in both Spanish Renaissance literature—the study argues that this seminal printed book is also of great importance to the history of music, particularly when the role of the songs composed for it (as preserved in the Cancionero Musical de Palacio manuscript) is fully understood. Indeed, this examination of what I call Encina’s ideal Cancionero reveals the cohesiveness of an unprecedented project that integrates prose, poetry, music, and drama, shedding new light on the author’s contributions to these arts, with particular emphasis on the role played by his villancicos, canciones, and romances within his broader artistic vision. Furthermore, the study illuminates Encina’s life and production in the Spain of the Catholic Monarchs and in Rome during the papacies of Alexander VI and Leo X. In this context, it offers new perspectives on the creation and reception of his works in Italy, as well as those of other Spanish musicians and playwrights—many of whom, like Encina, were of converso origin—active during that period. Finally, by understanding his art as an interdependent whole, this dissertation introduces new methodological tools to interpret his oeuvre, exploring the interrelationship between ekphrasis, intermediality, and music in the transition from medieval to Renaissance art. Through this approach, Encina emerges as a pioneer in music history—a figure who not only developed a rigorous approach to musical composition but also advanced an aesthetic vision whose influence, like that of his Iberian contemporaries, has been overlooked in Western music historiography.