The minimalist and absurd style of Samuel Beckett’s works seems to reduce his characters to a single confined space for the sake of tearing the trappings of plot, settings, and goals to what is essential: the mind. In his novels and short prose, the narrators—often the sole characters of certain existence—spend much of their time contemplating themselves, the reader forced into the tedious and confusing confines of their consciousness. In his plays, characters likewise move about in a small space with little in the way of motivation for action, leaving the audience and the characters with just themselves for company. In this, at least some element of Beckett’s lifelong fascination with rationalist philosopher Rene Descartes makes itself known through the deconstruction and reduction of the surrounding environment and actions to the one who perceives it. His trilogy of novels in particular—Molloy, Malone, and The Unnamable—charts a literal reduction to match the Cartesian metacognitive reduction by depicting, in order, narrators of declining physical abilities until the last of them appears as nothing more than a disembodied head. My intent in this essay is to analyze the evolution (or rather devolution) of the novels from this Cartesian context and relate it not only to the essential unearthing of the self, but the modernist existential revisions that complicate our concept of the self with themes like the failure of language as a means of self-creation and the ambiguity and ineffability of the self. An in-depth analysis of all three novels reveals this progression from shallower forms of uncertainty to total epistemological anarchy as the narrators’ questions dig to the base of what we know or may know.