Kant introduced critique not just as a concept to describe his project that has become paradigmatic for the way we think about philosophy in modernity. With the Critique of Pure Reason, Kant also presents the first iteration of a literary genre whose impact proved seminal for the way successive philosophical practice conceives of presentation as constitutive for thought itself. This chapter first examines the affinity to Montaigne’s project of the essay that resonates with Kant’s own approach to rely on writing as medium for critical reflection. Montaigne’s traces in Kant are a reminder of the importance of the mode of the essay for the emergence of critique as a new literary mode. It then examines how Kant’s pre-critical essays advance themes that prove central to the literary mode of critique as a particular form of writing. The chapter shows how the Critique of Pure Reason articulates its project whose architectonics bears not just conceptual but also literary significance, representing itself part of an argument whose literary construction cannot simply be separated from its “content” or conceptual make-up. Rather, critique emerges in Kant as a specific mode of reasoning that reflects form as constitutive to content. It then discusses the way Kant highlights the function of critique as Enlightenment and how the Enlightenment publicist as its “depositary” represents the cause as a literary mandate. The chapter concludes with a brief outlook on formative impact of the literary legacy of Kant’s critique from Marx to Critical Theory and Derrida.