It is well established that David Foster Wallace, the contemporary American writer known for his short stories and essays but probably best known for his 1996 magnum opus, Infinite Jest (1996), had serious and abiding interests in academic philosophy. To date, The Broom of the System (1987) remains one of the less examined works in Wallace’s oeuvre. The novel experiments with form and narrative, both showcasing Wallace’s heteroglossic skill and explorin non-traditional narrative techniques. As post-postmodernist writer, many critics point out that The Broom of the System is influenced by the Ludwig Wittgensteinian theories of language and communication. This essay will analyze The Broom of the System, in terms of the postmodern aesthetic, especially its concern for, and crisis about language, reality and self towards Wallace’s engagement with Wittgenstein’s theory to consider the relationship between functionality and identity. This essay will delineate not only how the distinction and tension between self and other pervades The Broom of the System and but also how (unsuccessful) attempts to construct a stable self rather displays the state of constant anxiety about language, self, and functionality in The Broom of the System.