This chapter explores Kerouac’s rich understanding of literary history as manifested in his Duluoz Legend, focusing in particular on two mechanisms by which this understanding turns up in his work. The first mechanism was his deep desire to seek and speak the truth, as he wrestled with his need to lead a godly life, a product of his Catholic upbringing, while simultaneously recognizing the almost requisite demand that a great novelist experience the darkness of the human soul. The second is the confession, which was not the legal confession of a court room or the spiritual confession of the church, but the broader truth of any human being who follows a path to forgiveness and wholeness by repeatedly purging themselves of sin, guilt, or embarrassment. Kerouac consistently worked truth and confession together – often to the dismay of some readers – twinning and twining them as he grappled with his spiritual and bodily identity as an American writer living in two conflicting Americas, the “the essential and everlasting America” of the ethereal beauty and mysticism, and the post–World War II triumphalist America of materialism and militarization.