Focusing on the work of Stanley Cavell, Richard Rorty, and Cora Diamond, this chapter shows how twentieth-century academic philosophy in the United States can be characterized in part by an ongoing interest in and exploration of the essay as a philosophical form. In a pluralist spirit, these explorations approach the essay form as a place to rethink and remodel what philosophical argumentation might look like. Related to this work of reimagining, such writing addresses the proximity of philosophy to literature in two senses. First, it is attentive to the potentially literary, written character of philosophy. Second, it is characterized by an interest in taking up works of literature philosophically, as a continuation of philosophical analysis and as a means of immanent criticism precipitating questions about philosophical analysis itself. That the essay became a salient form for these philosophers reflects their methodological radicalism. Each asks questions about philosophy as a kind of writing, and, as Rorty noted, writing tends to come to the foreground in periods of disciplinary crisis or radicalism, when the implicit “stage-setting” of a discipline comes under question.