Jake Heggie, American art song and opera composer, began his association with Sister Helen Prejean, CSJ when he composed Dead Man Walking, an operatic adaptation of her memoirs. Though from two very different backgrounds, the two developed a deep friendship and spiritual bond that provided the impetus for further compositions dealing with spirituality. Heggie adapted Prejean's meditations as a text for his song cycle The Deepest Desire in 2002, producing what he considers to be his finest work to date. Using The Deepest Desire as a gateway, this paper explores the social and cultural aspects of their association, revealing their personal perspectives on their relationship, collaborations, and shared sense of spirituality. Chapters include the biographies and spiritual philosophies of both Heggie and Prejean, Heggie's compositional style, Dead Man Walking, a performance analysis of The Deepest Desire, and the continuing influence of the relationship between Heggie and Prejean on Heggie's work. The appendix includes transcriptions of personal interviews with both individuals, Prejean's original meditation texts, correspondence with Heggie, Prejean, and Joyce DiDonato, and performance notes for The Deepest Desire derived from a musical coaching with the composer.