In many ways, _Infinite Jest_ was the quintessential 1990s American novel -- the conceit of the story was that American economic and cultural influence would simply keep growing and growing in the future -- as indeed in those heady post-Cold War times it looked like it would. Of course, part of Wallace's point was that would not necessarily be a good thing given the crass commercialization of US culture -- his idea that names of calendar years would be sold to the highest bidder is entirely believable given that we live in the world of PETCO Park and Qualcomm Stadium.
Many people have compared Wallace to Bret Easton Ellis (Less than Zero, American Psycho), and in a way they have a point. Certainly, Wallace was far more erudite and literary, but just as Ellis captured the "soul" of Reagan-era America, Wallace did the same for the Clinton era. Who will do the same for our current era?