Some who admire David Foster Wallace assert that those who don't "get" him or are guilty of misunderstanding what he's doing as a writer. If they are missing the point so often over the entire length of his talk, the fault is not entirely theirs. DFW had a habit of reflexively resorting to a passive "ironic" tone when the ideas in his work piled up under the weight of his un-diagramable sentences, which is a handy way of getting a laugh and riffing on end.
His point, his warnings, his insights became nearly unnoticeable for all his showing off. If there is a disconnect between audience and speaker, Wallace shoulders much of the blame. He was a fascinating writer and occasionally brilliant, but his lack of emphasis when it counted did him no favors. He did so many digressions as a means of revealing what's behind the narrative curtain, analogous, I suppose, to the grand scene in Wizard of Oz as Toto reveals that the Great Legend is both social construction and a fraud, that the brilliance is made indistinguishable from the exuberant and chatty bullshit that glut Wallace's writing. Wallace couldn't resist the impulse to comment, dredge for ironies when natural contradictions didn't avail themselves, serve heaping amounts of what read like undigested research. It was such a massive dump of information that what he'd written in his fiction transformed from the precious element of "telling detail"--that bit of commentary on specific items in a room and the speech acts of characters revealing some submerged desire to contradict and flee the world they've created or have selected--into mounds of unconsidered data.This always struck me as a species of hording, if you will; perhaps he was a rigorous editor of his own material in ways unknown to us, far too much of his work reads like a man who couldn't throw out paragraphs or pages that didn't bring quality to the reading experience.
There's a "look-ma-no-hands" showiness about his books, Infinite Jest especially. I suppose that as one who has made his way through a bevy of Henry James, James Joyce and Thomas Pynchon novels, all thick, labyrinthian, very extended in their conditional constructions who managed both to comprehend (I think) and enjoy the deluges of word virtuosity, I guess it's ironic I'd find Wallace's prolix tiresome. Not really. The other three were (are) better writers who wanted their sentences to contain surprise and ideas while not sacrificing the providence of tale they were engaged in telling. I never thought Wallace graduated beyond the status of being a loquacious verbal show-off.