What is it about the songbook of Bob Dylan that continues to captivate our deeper yearnings for meaning and hope in a world so dark and broken? While Dylan’s songbook has been analyzed in numerous studies, whether as classical literature, as scriptural theology, as mystical prophesy, or as the musings of a Zen master, the present study, God Knows Everything is Broken, aims to be a “generative” exploration of the depth and breadth of Dylan’s songbook in as of yet unexplored registers by examining the uniquely cynical but coherent gnostic theology within the arc of his lyrics. What continues to be underappreciated is how Dylan’s great American songbook—both in his original songwriting as well as covers— expresses a relentlessly downbeat world weariness as a way of navigating a world unworthy of complete redemption. By reflecting on this Nobel Laureate’s deft intertextuality that creates a new American scripture, God Knows Everything is Broken draws together the constellations of creative cataclysms in Dylan’s songbook as a uniquely dark expression of what he refers to in “Desolation Row” as Ophelia’s religion— that is, nothing but purest of American Religion. Dylan’s songbook is a playful but profound, catchy but nuanced trajectory into deeper darkening constellations of love lost, time unredeemed and faith broken. By reading Dylan’s American songbook as gnostic is to problematize the tendency to pigeon-hole one who is “busy being born” over five decades not as being “born-again” into Christianity, or “returning” to Judaism, but as a master of masks being designed, dawned and discarded in a series of creative cataclysms that continue to take hold of our imagination through iconoclastic lyricism. Dylan’s songbook is a testament to a constancy in creative rebirthing that mirrors the cosmos itself amidst its brokenness. God Knows Everything is Broken uncovers Dylan’s meandering direction home in his singularly ingenious gnostic songbook that opens a new window in to the death and rebirth of the American Dream.