This throwaway death-anniversary tribute headline, if his work informs us at all of the man, would make David Foster Wallace turn in his grave exactly eight years after he hanged himself in his garage, leaving behind a two-page note for his wife and an unfinished manuscript titled The Pale King, since published in 2011.

“Troubled” and “genius” would have made him wince, for they are oversimplified labels practically all of Wallace’s writing resists tooth and nail in all its verbose, foot-note-and-end-note totting expanse, whereas its resistance to deconstruction is a key to understanding the craft of easily the most original American writer of the generation gone by – the definitive voice, (although he resisted being labelled thus), of Generation X.

Amy, Wallace’s sister, describes him as a very, very secretive person, and Wallace’s history gives his fans plenty of reason to believe that. Picture being an anxious, self-conscious and highly intelligent man having tasted success as an avant-garde writer in your early twenties, repulsed by the very American pop-culture you are immersed in, and contrast it with an upbringing battling severe depression as early as sophomore year at Amherst College.

Picture anti-depressants, suicidal tendencies, and a deep sense of solitude in the midst of the recognition. Picture drugs and alcohol addiction, then drugs and alcohol rehab. Picture having a crush so hard you get her name tattooed on your shoulder and drive unannounced to mow her lawn, unasked, only to be spurned – picture all this, and you might see the origins of Wallace’s resistance to your entry into his space through his work, his hiding behind virtuoso smarts and crafty sentence, his preference, as Gary Hannabarger describes it, for “cleverness, facility, pyrotechnics” complete with Wallace’s self-professed disdain towards the reader in his early work.

Behind more and more masks

The Broom of the System and Girl with Curious Hair both display these concerns of self-revealing, and the pyrotechnics of avant-garde writing in the post-modern culture. Equally revealing of Wallace’s talents was the success these books received, so that by 28 he was already a literary star, recipient of awards, but his interest in these ways was waning, writes DT Max – Wallace’s biographer in “Every love story is a ghost-story”.

Wallace’s fiction had stopped, and he wrote to Jonathan Franzen of being a “pathetic and very confused young man, a failed writer at 28, who is so jealous, so sickly searingly envious of… any young man who is right now producing pages with which he can live”. It is at this time that his perception of writing changed drastically, aided in huge part by poetess Mary Karr’s spurning of his borderline stalker-like affections, and her suggestion that Wallace’s preoccupation with cleverness was “preventing him from saying things”.

This change, so starkly visible in Wallace’s writings since, turned his talents into the direction that gave the world his masterpiece on American culture, Infinite Jest. From this novel on, Wallace’s name was to become almost synonymous with sincerity in a world that was hiding itself behind more and more masks, be it entertainment, technology or advertising. In fact, all of Wallace’s phases are evidenced in the book, from the snarkiness and playfulness of his Broom days, all the way to the plain sincerity of more mature times.

The book, informed by Wallace’s own trysts with competitive tennis and rehab, as well as his extraordinary powers of observation and a major in philosophy and mathematical logic at Amherst, was the magnum-opus that redirected his genius, in my opinion, from investing in hiding his own deep, inarticulate-able quote-unquote “troubles” to the analysis of the unhappiness and hidden recess of the world around him, especially America. In Infinite Jest Wallace melded personal experience – the main characters are pro tennis players, a bunch of people at a halfway-house and Boston AA members – observation, research and an infinitely multifarious capacity for narrative language in answering the governing dynamics of “Why people do the things they do, including himself” in contemporary American culture.

Difficult but seductive

In Infinite Jest and all his subsequent works, Wallace dove deep into everyday mundanities and highly difficult subjects such as loneliness, addiction, boredom, the insidiousness of entertainment as a way of life, and attempt to unravel layer by personal and cultural layer the effects these grand patterns left on our minds. Naturally, therefore, his writing reads like not a nuance had been missed in long, multi-claused and jargon-filled sentences that spanned lines and paragraphs that spanned pages, not to mention the end-notes which had notes of themselves. This writing was a post-modernist ruse; it was a necessity – a tribute to the layers of the mind which, Wallace believed, was doing too many things at the same time to be articulated.

In a way, his genius was in proving himself at least partially wrong, for his pages teem with revelations both personal and universal in all their sprawling, chaotic complexity which make him at his best a prophet and at his worst unreadable. Both these phases exist in Infinite Jest especially, on purpose as Wallace revealed in interviews, because he wanted the book to be difficult but seductive, hard but rewarding – all that he wanted to be to Karr as well, for he wrote once that Infinite Jest was just the means to the end that was her.

Brevity, thus, was a problem for Wallace; in a lot of ways his style was the antithesis of Hemingway’s, though both had their roots in journalism. Here also Wallace’s preferences for the unimpressionable and mundane are visible, for while Hemingway’s beat was war, Wallace devoted his journalism to things like cruise-ship holidays (a supposedly fun thing I’ll never do again) and Lobster festivals (Consider the Lobster), committed to understanding the pervading “water” of the everyday he pointed out to students at Kenyon College in 2005 in perhaps the greatest commencement speech of recent history.

Alas, Wallace himself was too aware of this “water”, so much so that he preferred to drown in it. “The thing about people who are truly and malignantly crazy: their real genius is for making the people around them think they themselves are crazy.” he wrote in Infinite Jest. There was always a spectre of craziness about David Foster Wallace; one that has even been further gratified by his suicide at 46, but the magnificence of this writer was that he showed us that we – or America, at least – were no better or worse than him.