This long overdue reevaluation of Jack Kerouac gives fresh perspectives on his unique literary output, his vexed relation to issues of race, class, and gender, as well as his continuing cultural afterlife. This collection of essays by esteemed Beat commentators reassesses one of the 20th century's most emblematic but often misunderstood American writers. Despite amassing a substantial body of influential work and becoming a recognizable icon globally, Kerouac has often suffered critical neglect, and this volume seeks to offer a range of fresh perspectives on his unique artistic output as well as his continuing cultural afterlife. Through an examination of classic texts like On the Road to more obscure ones like Pic, these essays recalibrate our understanding of the writer by placing his creative output into dialogue with current cultural issues to provide a rethinking of how concerns such as race, gender relations, artificial intelligence, populist rhetoric, and queerness inform his work and its contemporary reception. These essays also examine how the peculiarities of global circulation and social media influence the ongoing cultural appropriation of Kerouac in popular music, literature, and online. Through these varied approaches, Rethinking Kerouac: Afterlives, Continuities, Reappraisals provides an indispensable account of the continued relevance of both Kerouac the writer and Kerouac the cultural icon in the 21st century.