Infinite Jest was the first thing I read by David Foster Wallace. I think it was back in the summer of 2004. It was only years later that I got around to any of his other work. Flipping through Consider the Lobster today made me realize that DFW really earned his take on American culture. He went on the cruise, he interviewed the right-wing radio jock, he sat through the porn awards, he got out there and mixed it up. (Although perhaps he only got this kind of access after he'd written his big book…) At any rate, I think a second trip through Infinite Jest will be pretty rewarding once I've read a bit more of the non-fiction.
I'm usually inclined to speculate from the comfort of a comfy chair whenever I can. But there's a good case to be made that comfy-chair critics should be ignored whenever possible.