This book examines literary texts from various genres -- prose fiction, plays, film -- in order to explore the way dark and enlightening spiritual journeys are presented in literature. Combining literary criticism with Jungian approaches, the analysis focuses on well known religious, spiritual and psychological writings, with special reference to the work of James Hillman. Stanley Kubrick's film 'Eyes Wide Shut' and Nathaniel Hawthorne's classic tale 'Young Goodman Brown', which present uncannily similar stories, exemplify the book's theme: both are examples of a "dark-side" narrative. In each case a limited, somewhat naïve protagonist goes out, at night, into the darkness (the streets of New York in the case of Kubrick's protagonist, the New England forest in the case of Hawthorne's) and discovers things about himself and the world that he previously was unaware of. It is a disturbing discovery of deep imperfection and apparent perversity -- an encounter with what Jungian psychology dubs "the shadow". But it is also an experience of what Christian theologian Paul Tillich calls "depth", which he considers an experience of groundless mystery that is no less than an encounter with whatever people refer to when using the word "God". That a discovery of apparent perversity may be an illuminating experience of the divine is a paradox that lies at the heart of the mystery of each individual's "shadow", no longer to be considered as a bundle of repressed negativity but as a harbinger of growth and soul, a doorway to spiritual illumination. In Shadows and Illuminations this paradox of dark-side narratives -- that shadow is illuminative -- is explored in relation to a variety of classic and contemporary literary works.