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This paper is a scholarly and soulful inquiry into the iterative relationship between Merle Haggard's struggle to find his way through life and his artistic quest. The paper explores the roots, the meaning, and the working through of personal challenges through Haggard's songwriting and performing, aptly applying psychoanalytic perspectives on development and adaptation to traumatic loss. The analysis follows from biographical and autobiographical accounts of Haggard's life placed in relation to the lyrics of his songs, and explores the reactions of the young Merle to the painful loss of his father and the ambivalent attachment to his mother. Wheeler's approach to the music focuses on the poetry of the lyrics, employing the same kind of scholarly textual analysis that has characterized his considerations of the works of Shakespeare, D.H. Lawrence, and others.