This article focuses on the relationship between philosophy and literature in J.R.R. Tolkien’s essay “On Fairy-stories.” Delivered as a lecture in 1939 and published in 1947, the text presents the author’s conception of the literary genre known as “fairy-stories” and, in this article, I explore the possible philosophical and theological mediations and references in Tolkien’s investigation. The objectives of this article are twofold: to highlight the literary theory proposed by Tolkien as part of the philosophical tradition of medieval realism, with conceptual correspondences in Plato, Aristotle, Augustine, and Thomas Aquinas; and to demonstrate Tolkien’s original contribution to the appreciation of imagination and fantasy as a form of contemplation. The methodology comprises a comparative bibliographical review of these authors, using both the essay by J.R.R. Tolkien and his personal letters, as well as the books by the above-mentioned philosophers and their contemporary commentators. The conclusion upholds the viability of the connection between the philosophy and mythopoeia conceived by Tolkien as a contemplative way that values the production of myths as a means of admiration of reality from the metaphysical perspective.