Another thought on Infinite Jest. There is sometimes a soulless tendency in postmodern art. If the artist is not careful, all their philosophizing and meta-this-and-that can lead them into the twin blind alleys of nihilism and/or smugness. Clever enough to deconstruct and poke holes, but not clever enough to build anything back up after tearing it down. It's that sterile art-gallery feel.
This is why I really love the sections of IJ that deal with Alcoholics Anonymous and the Ennet halfway house. These sections (so far) have a big beating heart. The vibe is not "there is no truth!" but rather, "truth is everywhere, and it is messy and doesn't make sense, but you can find it somehow." The section I just read (p. 343, not really a spoiler) was making the point that AA works even for addicts who don't believe in god and who think AA itself is a bunch of cliched b.s. The whole thing was charmingly meta, and also kind of old-fashioned.
It reminded me (tangentially) of Charlie Kaufman's movies (primarily Adaptation and Eternal Sunshine) where he uses all manner of narrative and digital trickery to elevate plots that are not so different than 100 cookie-cutter romantic comedies when you get right down to it.