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.