In JRR Tolkien’s legendarium, there are evident connections and allusions and allegories to other works of particular importance to the Western canon. These include the Bible, Joseph Campbell’s writings on the Hero’s Journey, and Carl Jung’s psychological theories. This paper suggests that these different strands of thought circle around each other, addressing in their own ways the fundamental relationship between the Self and the Other dressed up in different guises. Adopting Jung’s concept of the Shadow, this paper will argue that the confrontation with and assimilation of the Shadow, the profound eucatastrophe, lead to the experience of the numinous, which is reflected across these different works and particularly in Tolkien’s writings. Using a reader-response lens, the power of this experience will elucidate the enduring power of Tolkien’s oeuvre, both for the author and the readers.