I am still working out why this matters to me so particularly - in a way it wouldn't with another prominent writer.
I was actually pretty snarky about Infinite Jest when it came out, and mostly I stand by that, and I kind of thought I had put him in his place, mentally. The turning point for my feelings about DFW was a review in the New York Review of Books by A. O. Scott, which I remember as saying, roughly, "Sure, Wallace does a lot of fancy formal experimentation, but for his cohort that's kind of the norm; he doesn't do it to impress, he means it. Ie he's really in it, he's not just trying to look smart; it's just that the problems are so hard that he has to be smart and do his performative stylistic tricks because he needs to make language tell the story he needs to."
I just got through re-reading Consider the Lobster, and it was only just striking me how valuable his writing is - there's something exquisitely fine-grained about how DFW encounters the collisions of class and taste and politics and morality happening in contemporary culture, wherever he happens to be - the Iowa State Fair, a cruise line, in Iowa City on 9/11, and -crucially - following the McCain campaign in the 2000 Republican primaries - where picks apart how impossible it is to really know the candidate at the center of the campaign machinery. I say "fine-grained" not because he writes about trivia but because he registers distinctions, tensions, that are pushing on us all the time and are almost impossible to be aware of every second, and somehow he makes his prose do that. And so I thought we were going to have him around for longer than this; in fact I was kind of counting on it.
And: DFW always seemed maddeningly (to me) absent from his own prose. He writes these experiential non-fiction articles where he's sent to wherever, and the comedy is in the collision between his blue-state sensibility and some mass demotic event, so he has a persona of sorts, neurasthenic, hyperaware outsider stumbling through the vulgarity, entranced, horrrifed, periodically humiliated, but always narrating with a perfect openness to all the sensations involved. That sensibility is the centerpiece, but the personal stuff is conscientiously omitted - he manages to put his perceptions out there without the rest of him, which is part of the charm. You're always expecting the snobbish or Woody-Allen-hapless persona to make its entrance, and it's always surprising to get to the end without having seen DFW himself. (especially when you turn over the book to find the author photo, which is nothing like what you've imagined)
Likewise his fiction (I couldn't finish either Broom of the System or Oblivion so it's not like I have delusions of critical authority here) doesn't use obvious author-surrogates, the closest being the tennis student of Infinite Jest; which doesn't detract from the emotional impact - long passages talk about what it feels like to be these characters, and it's moving and precise - but it's almost spooky because you don't know who could possibly be writing it except that they went through it personally, but where exactly is that person?
I've gone on too long with this undergraduate-style appreciation, but this why the decision he made to end his life is so disappointing: His review of Updike's Toward the End of Time, is a demolition of the book in question and of, at least, the later work of Updike, Roth, and Mailer, the "Great Male Narcissists" (GMN's), the absolute triviality of writers so obsessed with their bodies, sexual powers, and the gradual disintegration of same, which they endow with cosmic significance.
DFW took issue with that, so rightly, and I couldn't help but take him as a counterexample, someone whose writing took him and his ego out of the equation, but in his hyperacute application of language and formal experimentation was looking for a way to put himself back, in a way that didn't violate a deeply held feeling of obligation to the medium. His essay "Joseph Frank's Dostoevsky," I think speaks to a conviction about the ethical force of literature, the stakes of literature, and reading now I feel that a lot of his stylistic flair was in the service of those stakes. DFW is 46 and I am 39, and so I had hoped to have him around to give advance word as to how one might face those events differently than the GMN's had done, as a writer and as a human being.