This chapter explores the inherent ambiguity in the meaning of “spirituality” through a musicological analysis of Outlaw Country. The musical genre, beginning in a rejection of the Nashville recording process in the 1970s, is marked by an interpretation of more traditional religious themes into spiritual symbolism. The ambiguity of spirituality appears in both the lyrics and music of Outlaw Country as a form of dissonance. Willie Nelson, Sturgill Simpson, and Cody Jinks serve as examples of this dissonance. Even more, the translation of religion into spirituality imitates a broader cultural shift, which is tracked below through the work of Charles Taylor. Both of these analyses claim that the meaning of spirituality cannot be pre-determined, but can only be discovered by exploring where it becomes reality in aesthetic events. This claim coincides with the general thrust of German aesthetics, as it is developed in the twentieth century through thinkers such as Paul Tillich, Martin Heidegger, and Hans-Georg Gadamer. The value of this view of aesthetics is most evident in the emphasis on the symbolic nature of reality and in seeing music as an exemplary aesthetic form in this regard. Both of these aspects provide a suitable means to gain an understanding of the meaning of spiritual that is realized in Outlaw Country.