Not normally considered a philosopher, the novelist Miguel de Cervantes nevertheless touched upon many of his eras most important philosophical themes. After a representative sampling of what might be called philosophical moments in Cervantess works, we shall proceed systematically to examine his connection to three distinct philosophical schools or movements: skepticism, cynicism, and sophistry. We shall then consider some innovative and original aspects of Cervantess thinking by comparing him to first Plato and then to Descartes. Finally, we will conclude with his views of both epistemology and ontology before saying a word about his legacy and influence on later philosophers.