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Because he wrote in the latter half of the twentieth century, and because he was labeled a “hyperarticulate Tin Man” (and other similar things), Wallace is most often placed in the postmodern cabal, among the likes of DeLillo, Vollmann, Pynchon, Gaddis, Gass, and Barth—who was the literary “father” Wallace supposedly had to “kill,” if you believe in the Titanian mythos of patrilinear succession in American literary fiction. Unlike the novels of most postmodernists, however, Wallace’s are not a martyring challenge to read—absent from Infinite Jest are the willfully obscure stylistic choices that make slogging through something like William Gaddis’s J. R. such a Herculean task. To read Wallace, all you really need is a little endurance and a willingness to crack the dictionary. In fact, Wallace’s fiction is so humane and accessible compared with that of his contemporaries that scholars like Marshall Boswell have suggested that he might be something different from the postmodernists altogether. As Boswell writes in his 2003 book Understanding David Foster Wallace:

Although Wallace is often labeled as a “postmodern” writer, in fact he might be best regarded as a nervous member of some still-unnamed (and perhaps unnameable) third wave of modernism. He confidently situates himself as the direct heir to a tradition of aesthetic development that began with the modernist overturning of nineteenth-century bourgeois realism and continued with the postwar critique of modernist aesthetics. Yet Wallace proceeds from the assumption that both modernism and postmodernism are essentially “done.” Rather, his work moves resolutely forward while hoisting the baggage of modernism and postmodernism heavily, but respectfully, on its back.

It’s true that Wallace’s writing borrows as much, if not more, from Ulysses and To the Lighthouse as it does from The Sot-Weed Factor. That said, I agree with Boswell that it is difficult to identify Wallace as a dyed-in-the-wool member of any aesthetic movement. Wallace was more concerned with honestly transcribing the particulars of his world than he was with self-consciously aping any literary trend. He once spoke with disdain about “the crank turners, the little gray people who take the machines others have built and just turn the crank, and little pellets of metafiction come out the other end.” It seems fitting that his aesthetic is “still-unnamed (and perhaps unnameable)”; he built a literary machine, and many young writers are dying to turn its crank.

In an artistic climate in which it is fashionable to be distant, coy, and “mysterious”—to sit like a god above your metafictional work and pare your fingernails while the reader struggles on in futility—Wallace is something of a relief: warm, vulnerable, self-effacing. He wrote with a big-hearted curiosity about the world around him; if anything, that’s extremely charming.

The stories about Wallace are not the same sort of gonzo stories one hears about other contemporary writers. Unlike T. C. Boyle, Wallace did not soak his feet in chicken blood while he wrote, and he eschewed William Vollmann’s practice of befriending skinheads (although Wallace did hang out in a lot of halfway houses while researching Infinite Jest). Rather, one hears about Wallace’s tremendous sense of humor (he was so entertaining that fellow undergraduates at Amherst referred to him as the “Dave Show”), his tendency to adopt dogs whose former owners had abused or mistreated them, and the patience and respect he devoted to his English students. There’s also a good deal of talk about his humble beginnings. It’s remarkable to some people that the man who authored Infinite Jest grew up in the rural Midwest. It comes as no surprise, however, that his father was a philosophy professor at the University of Illinois and his mother an English professor at a local community college. Wallace excelled in sports from an early age; as a teenager, he was one of the highest-ranked football players in the township. In his early teens, he made the move to tennis, a decision supposedly motivated by his lack of bulk. By his late teenage years, however, he had emerged as an athlete-cum-frenetic intellectual. The decision to attend Amherst, his father’s alma mater, seemed a natural one, but Wallace was severely homesick and emotionally unstable as an underclassman and ended up having to take time off. He told David Lipsky, author of Although of Course You End Up Becoming Yourself: A Road Trip with David Foster Wallace (2010), that during this fraught period, he was placed on a mood regulator that made him feel like he was “stoned and in hell.” Despite his struggles, he graduated summa cum laude in 1985 with degrees in English and philosophy.

After Amherst, he attended the University of Arizona’s MFA program and published The Broom of the System, an anti-Künstlerroman that’s an explosive synthesis of Wittgenstein’s philosophy of language and Derrida’s literary criticism, while still a student there. In the early 1990s, he abandoned a doctoral program in philosophy at Harvard and sought a teaching position in the English department at Emerson College. He’d found his calling as a teacher of English and creative writing, and he would remain one thereafter: he accepted positions first at Illinois State University (1992) and then at Pomona College (2002). By 2003, Wallace had received a MacArthur Fellowship and had published stories in the Paris Review and the New Yorker and essays in Harper’s, among other places (several essays were published in his collection A Supposedly Fun Thing I’ll Never Do Again). He had a light teaching load at Pomona, which gave him freedom to focus on his writing—especially the completion of The Pale King.