But no matter the degree one believes there is any real conflict going on at all, it’s still tempting to see DFW as a kind of particularly farsighted scout, who left behind copious, obsessively detailed notes about what loomed on the horizon, and then quietly departed the battlefield before things got really hairy. This humble cruise essay is not only one of the best and most illuminating of his field reports, but also, and I truly believe this, one of those pieces that will be honored, in the way someone like Montaigne or Shakespeare is honored today, by people three-hundred years from now who will look back on and declare DFW’s cruise essay as ‘one of the first truly modern pieces of writing’. Whether or not this is a good thing, is of course determined by our own relationship to pleasure, and to what degree we believe the world should be designed to provide it to us.

This, the early 21st century, is the excruciating moment, and DFW’s work the scream. In dismissal of his work as pretentious, or his fears as misplaced, I detect the same impulse as what is in work in us when we dismiss real concerns over youngsters and their iPhones as stodgy and pointless. Collectively, we are unsure if there is something behind our shoulders, some horrible unforeseen price to be paid for the ever accelerating race towards low-risk, low-investment hedonism, and the universal pampering to our needs not just as consumers of food and drink, but of novelty, insipid social interactions, and status games. 

One of the reasons I liked all these women (except Mona) so much was because they laughed really hard at my jokes, even lame or very obscure jokes; although they all had this curious way of laughing where they sort of screamed before they laughed, I mean really and discernibly screamed, so that for one excruciating second you could never tell whether they were getting ready to laugh or whether they were seeing something hideous and scream-worthy over your shoulder…

To a critic who saw Dante and Shakespeare as the beating heart of all past and future literary achievement, I can see how DFW’s writing could come off as mere hand-wringing, the vain navel-gazing of a virtuosic undergraduate that has gained praise merely because it has been pushed to it’s absolute limit in both verbosity and vulgarity. But that is more the aesthetic of Wallace than the core of him; he aimed to relentlessly entertain and enthrall through complex configurations of plot, character, and form, whilst imparting, or at least suggesting, moral imperatives with the confidence and power of the old Russian greats.

Book Review: A Supposedly Fun Thing I'll Never Do Again