I had read it the first time around ten years ago, highly recommended by friends of mine. The first time, I didn't start out reading the footnotes. So, if you decide to tackle this novel, that's my first recommendation. Definitely read the footnotes (there are around 100 pages, and the characters and plot are sometimes further explained in them).
The book is long and descriptive - instead of minimal language - it's more like maximum, obsessive language. The Onion satrized it here; where David Foster Wallace's girlfriend stopped reading his 67 page break up note on page 20.
That's my second recommendation about the book. Wallace explains a lot within the first hundred pages and actually wraps up some threads in the beginning. I know that might not make sense, but that's what I found. So you might read through the entire book the first time, then re-read to page 100. Some of the characters make more sense - including one (single) sentence, in which two of the main characters meet (Hal and Gately). But, the first time through, you aren't looking for either character and just trying to figure out what's going on.
I also recently listened to the Slate book club's analysis of the book. They read the novel in March of 2008, around six months after the author's death. * I also agree with the claim about Consider the Lobster, a collection of essays.
I have to admit, there are some parts that do seem excessive. I know that Wallace claimed that everything in there was supposed to be there (the original draft was 1500 pages) but some things do seem over-extended. But his descriptions of everything involved with addiction were intensely powerful. Particularly this second time, addiction and obsession popped out at me. It's true, every character has at least one thing (or multiple things) they are obsessed with - which prevent any real human relationships or interaction. In that sense, it's really not a dark comedy - but a dark vision of humanity. The chapter where a minor character is preparing to smoke pot on a bender (for example) - this is the eightieth or so time that he has sworn he will never smoke pot again - that he's told everyone in his life he's never smoking again...but here he is, preparing to not speak to anyone for three days while he smokes. I can't describe the chapter well here - I highly recommend reading it yourself.
Or the part about how a person realizes that the substance they thought was their "one true friend", there throughout it all, is really not friend at all. That the substance has taken away everything a person has ever cared about, including their sanity. Instead of being described as "hitting bottom", that a point that some addicts reach is more like a cliff - where they realize that if they are going to stay alive, they have to do something different - to change. Because there is no way they can keep going the way they are and survive.
I agree with the book club analysis. Personally, I will go on a limb and suggest that there is no way that he could have written everything he did without being some sort of addict himself. (Maybe one of his assertions is that everyone is some form of addict?) I don't actually know if he did struggle with addiction with illegal substances, in looking back through the obituaries, I can't say for sure that he did.
If anything, my hope is the novel might help encourage understanding of addiction and obsession.
On the other hand, that is what makes some novels great, isn't it? When the author might not have anything in common with the main characters or their experiences; but it seems like there is no way they could write about it without having experienced it.
It's a long book, I can respect that some people like it, some people don't - that it's controversial. I feel the second time around, I understood more of what was going on.
* So people didn't really finish the book? Really? Granted, it is 900 pages long. I can see that with some other novels, but the pacing seems to keep up with Infinite Jest. And you keep wanting something to happen, for things to resolve, for things to make sense (perhaps futile).
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