Something most readers notice right off the bat is that Wallace is, simply put, a very difficult writer. Some people supplant this word ‘difficult’ with other ones, like experimental, avant-garde, or aesthetically-daring. Less smitten readers have probably used words like tedious, show-off-y, or unnecessarily verbose. Bruce Weber’s New York Times obituary called him “grammatically and etymologically challenging.”  The literary critic James Wood lumped Wallace’s work—along with that of Zadie Smith, Salman Rushdie, Thomas Pynchon, and Don DeLillo—into the derogatory category of ‘hysterical realism,’ a literary trend towards maximalism crippled by an over-saturation of interesting but mutually implausible detail. I, for one, filled an entire cow-print notebook with vocab words while reading Infinite Jest.[4] And given the (sometimes myopic) attention paid to this element of his work—what Wallace himself called his ‘formal stunt-pilotry’—it seems important to ask the question, one which has more than once crossed my mind while reading Wallace: does it have to be this hard?

Let me answer like this: there is a line in an essay from An Incredibly Fun Thing I’ll Never do Again where Wallace is talking about his “near-great” but abruptly-ended adolescent tennis career where he says, “I was at my very best in bad conditions.” To be a good tennis player, Wallace tells us, you have to “think n-shots ahead, where n is a hyperbolic function limited by the sinh of opponent’s talent and the cosh of the number of shots in the rally so far (roughly).”[5] But unlike most of his competitors, who were probably less bowled-over by advanced calculus and vectors and anti-derivatives, the young Wallace, a semi-closeted math nerd, could factor the indomitable wind of Central Illinois into his athletic calculations. The wind, rather than posing a competitive problem, was the source of his competitive advantage. His ability to deal most prodigiously with the constraints of playing junior tennis in tornado alley was precisely what made him great. Or near-great. Ultimately, it was in the absence of obstacles, when there were no special limitations within which to out-maneuver and out-think his opponents that Wallace qua junior tennis player floundered.  “Puberty-angst and material alienation notwithstanding,” he tells us, “my Midwest tennis career plateaued the moment I saw my first windscreen.”