Beginning in the year 1913, both C. G. Jung and J. R. R. Tolkien independently began to undergo profound imaginal experiences. They had each stepped across a threshold and entered into another world, the realm of imagination, the world of fantasy. For Jung these initially spontaneous visionary experiences, which he later developed into a meditative technique called active imagination, were recorded in Liber Novus, usually referred to simply as The Red Book. The experiences narrated in The Red Book became the seeds from which nearly all Jung's subsequent work flowered. For Tolkien this imaginal journey revealed to him the world of Middle-earth, whose stories and myths eventually led to the writing of The Lord of the Rings, a book he named within its own internal history The Red Book of Westmarch. Although they were working in different fields-psychology and philology, respectively-there are many synchronistic parallels between Jung's and Tolkien's Red Book periods: the style of the many works of art they produced at this time, the nature of their visions and dreams, and an underlying similarity in world view that emerged from their experiences. All these suggest the two men may at times have been treading parallel paths through the imaginal realm. The revelations of this research bring to the surface questions about the nature of imagination and its relationship to the collective unconscious and perhaps a cosmic psyche, which in turn may hold deep implications for modernity's assumptions of a disenchanted world. In this work, I point to the possibility that Tolkien and Jung are preliminary guides on a journey to the depths of an ensouled cosmos in which imagination saturates the very foundations of reality.