This chapter examines Kerouac’s later novels such as Big Sur, Satori in Paris, Desolation Angels, and Vanity of Duluoz, showing how he developed a “late style” that was a response to the way his image and writing were commodified by popular and literary culture. These late novels portray the author-narrator as out of step with a culture that has passed him by, as Kerouac suggests the ways his fame as the so-called “King of the Beatniks” led to both his increasing alcoholism, and to new ways of looking at himself in his writing.

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.

This chapter focuses on Kerouac’s last major novel, Vanity of Duluoz in the context of the 1960s. This novel was composed under fraught conditions as Kerouac labored under intense financial pressure to earn money to pay for his mother’s debilitating illnesses. Not only was it a struggle for Kerouac to complete it, the novel also powerfully documents Kerouac’s struggle with reconciling his traditional, “conservative” upbringing with the nascent “Beat” rebellious energies – born in the forties and continuing into the sixties – a conflict which this chapter explores.