This chapter focuses on the canonical essays that theorized in real time the new stylistic and thematic tendencies in American postmodern fiction. Since the late 1960s, prominent practitioners of postmodernist fiction have been at the forefront of critical debates over contemporary American narrative. From the 1960s to the 1990s, brilliant authors such as Raymond Federman, John Barth, Ronald Sukenick, and David Foster Wallace engaged in essayistic reflections on the problem of innovation in American fiction, including Barth’s “The Literature of Exhaustion” and Wallace’s “E Unibus Pluram: Television and U.S. Fiction.” Despite differences and generational distance, in some of their best essayistic writing these writers often focused on the (old) problem of “the new” in art, reframed as a discourse on the making or unmaking of the postmodernist aesthetic in response to a supposed exhaustion of literary language. They did so from a liminal position, namely from the ambivalent stance of the writer-critic, and ended up producing some of the most penetrating essays on contemporary American literature during this period, indelibly marking an era in the history of the American essay.