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The moral and aesthetic complexity of Cormac McCarthy's fiction demands sophisticated theoretical reading paradigms. Intertextuality informed by poststructuralism is a theoretical approach that enables one to read the moral and aesthetic elements of McCarthy's work in productive ways. McCarthy's work is augmented by its connection to the works of other great artists and writers. As a result, McCarthy's work forces us to read his precedents from a different framework. An examination of the conversation between Martin Heidegger, Meyer Schapiro, Jacques Derrida, and Frederic Jameson about Van Gogh's A Pair of Boots creates an intertextual framework for examining the connection between Cormac McCarthy's Outer Dark and William Faulkner's Light in August. This examination demonstrates that Cormac McCarthy provides a sophisticated aesthetic and moral critique of Faulkner. This application of intertextual theory can also be applied to better understand the intertextual connections that exist within McCarthy's own canon of work. The same discussion of Van Gogh's painting can be used to understand the significance of a pair of boots in McCarthy's No Country for Old Men. This analysis demonstrates that McCarthy has moved from a privilege of postmodern aesthetics in Outer Dark to a privilege of more modern cinematic aesthetics in No Country for Old Men. This shift in aesthetics also informs the moral universe in each novel. Understanding this shift in aesthetics also provides a useful framework for understanding the connection between All the Pretty Horses and its film adapation directed by Billy Bob Thornton. The adapted film of McCarthy's novel enables a productive reading of the tensions between modernism and postmodernism in McCarthy's work.