It's always dangerous to comment about a book before you've finished it. But in the spirit of Infinite Summer, let's give it a try anyway. (NOTE: In what follows I basically respect the Infinite Summer no-spoilers rule. I do quote a few words [about 75 of 'em, not even a full sentence] from page 382, and mention the names of some Marxian philosophers of culture who occur on page 450, but there are no real spoilers in what follows).
There are at least two areas where I think reading about the near-future setting of Infinite Jest seems especially jarring--where David Foster Wallace's future seems most clearly and emphatically not our own time (whatever year the Year of the Depend Adult Undergarment may be)--moments where, in an outburst of crassness, you might exclaim, "Boy was DFW wrong about that!" in the same spirit that you might say, looking back at the work of M.C. Hammer, "Boy, was he wrong about parachute pants!" Needless to say, that was never the point; Infinite Jest is a novel, not a prediction; and "parachute pants" are just biding their time, waiting for their moment.
I point out these two areas in the hope of better understanding what Wallace, in interviews (thanks to the #infsum folks on twitter for that link), described as the sadness at the center of the novel. Reading the novel, sadness is certainly not one's most immediate experience. While, less than halfway through, Infinite Jest has remarkable emotional range, it is more often funny than anything else.
Understanding this "sadness," I think, requires recognizing that such sadness is not the opposite of humor. Instead, sadness is something that is often communicated through humor. Just consider the ongoing Maranthe/Steeply dialogue. Their conversations, about the value of pleasure (w/r/t "The Entertainment") and the importance of "choice," form something like a philosophical backbone for the novel (a little Socratic dialogue amidst everything else). But Wallace never lets us forget the hilarious situation of these two speakers. Even as they engage in serious discussion, Wallace keeps reminding us of the comic scene in which this serious discussion takes place; the pretensions of both figures are comically undermined by Maranthe's butchered English, or by Steeply's adjustments to his bra straps. This makes the novel funny; but it doesn't mean that everything Maranthe and Steeply say is vacuous.
Part of the sadness in which Wallace seems to be interested is produced by a lack of meaning or purpose, which subtends even the novel's funniest moments. But what are these "two areas" I keep obscurely referencing, where the novel's future seems somehow unconvincing, and how are they related?
The Politics of O.N.A.N. - No small amount of the novel's humor comes from the rearranged political landscape it represents. It is hard not to find the idea of violent political tension between Canada and the United States inherently funny. Politics in the novel generally seems like a fool's game. There are no "politically committed" characters. Secondary political characters like Gentle or Rod (the God) Tine are essentially buffoons; they don't satirize particular political figures so much as they satirize the idea of politics itself.
In this regard, the imagined political landscape of Infinite Jest is very much a product of the early 1990s. ONAN is a sort of comically horrific NAFTA; ONAN is not Wallace's gesture towards "globalization" (the term that names our contemporary international political situation as well as any other) so much as a comically exaggerated extrapolation from the conditions in the early 1990s.
More broadly, Infinite Jest seems to participate (with some irony) in the early 90s sense that we are at the "End of History" and that all politics seems therefore emptied of significance. What respectable political commitments are even available anymore? As Joelle van Dyne walks down Boylston street, she sees a flag draped over the statue of Colonel Shaw: "the Canadian militants come in the night, on the eve of Interdependence, thinking anyone cares whether they hang things from historic icons, hang anti-O.N.A.N. flags, as if anyone not paid to remove them cares one way or other" (223 - 24). There is a sense that no one but cranks gives a damn about politics--to care about politics in this world seems very silly indeed. (I'm oversimplifying here. . . but am I totally off base?)
Later in the novel, Wallace describes the future (I'm being a bit vague here deliberately for readers who haven't gotten to this point) as
a post-Soviet and -Jihad era when--somehow even worse--there was no real Foreign Menace of any real unified potency to hate and fear, and the U.S. sort of turned on itself and its own philosophical fatigue and hideous redolent wastes with a spasm of panicked rage that in retrospect seems possible only in a time of geopolitical supremacy and consquent silence, the loss of any external Menace to hate and fear. (382)This future world of "geopolitical supremacy and consequent silence" is unlikely to strike us as compelling. The idea of being safely "post-Jihad" seems especially awkward.
What's worth noticing, though, is less how different our present is from Infinite Jest's, than the way such am imagined condition (even if we now find it quaintly fictional), leads to a loss of meaning; the absence of "any external Menance" deprives the world of a sense of purposefulness.
The Role of Technology - Written in the first half of the 1990s, the novel clearly apprehends the importance of technology for daily life. But it has no sense of the way the Internet, as a participatory medium, differsfrom television or other media. One might laugh at references to modems, or floppy (yes, floppy!) disk sizes that might have sounded impressive in 1996, but now seem inadvertently comic. But what I think really separates the technological world of Infinite Jest from our present reality is how Wallace imagines the Internet as a sort of glorified video-on-demand delivery service (Inter"lace" itself being a pun on Inter"net").
In Wallace's vision of the technological future, network technology doesn't seem to ever "bring people together" (to use one of those horrible cliches that Gately is teaching us to take more seriously). While, in the imagined future of IJ, video on demand poses a problem for advertisers, the "broadcast" model of culture remains firmly in place, just with a new technological infrastructure. In this sense "The Entertainment" seems a sort of nightmarish extrapolation of Adorno and Horkheimer's description of mass culture. (Adorno and Horkheimer get a passing mention on p.450; I find myself constantly wondering about Wallace's own attitude towards what A&H call the "Culture Industry").
Am I wrong in suggesting that in the future imagined by Infinite Jest, there would be no Infinite Summer? In the novel, technology doesn't afford opportunities for community-building, it just provides a more insidious avenue for consuming the same ole' same ole--for watching cartridges on a TP.
Both of these points, really, are about "politics" in the broad sense of collective life. And in both cases Wallace's imagined future seems a place especially inhospitable to collective meaning.
In noting these two points, of course, I don't mean to be saying "Boy, Wallace was really wrong about the future." Rather, I think, these discrepancies help us to understand how Wallace imagined the world and what aspects of it were most relevant for the purposes of the novel. Octopus Grigori, commenting at the Infinite Summer blog, wondered whether the Science Fiction aspect of the novel was even necessary. I think it is; but primarily as a means to get at the real questions in which Wallace is interested: the question of meaning and purpose.
George Orwell (to use the most obvious instance) uses science fiction in 1984 (just as he uses animal fable in Animal Farm) to explore fundamentally political questions, questions about social organization and the place of the individual in society. Wallace uses Science Fiction to investigate the experience of personal meaning--whether that "meaning" comes from tennis, drugs, or twelve steps. I'd wager that Orwell would think Infinite Jest is a novel located soundly "inside the whale" (to use Orwell's formulation for the turn away from political fiction after the 30s).
One avenue that seems closed to the characters of Infinite Jest (at least so far) is collective meaning or experience--that is, political experience. Technology affords only "entertainment" and politics is a joke.
(I think; I'm on page 475 right now...)