Infinite Jest

Less difficult than its reputation insists, which is itself a kind of tell, because the people most invested in the book being "Difficult", a feat, a thing you survive and then mention at parties are usually the ones who want the credit of having finished it without the inconvenience of having felt it, and feeling it is the whole point. The prose is by turns beautiful and haunting and absurd, and the subject matter does the same thing, mirrors it. Under all the footnotes, the recursion, the meandering sentences that test your short term memory is just a deeply, almost unbearably sad book. About addiction. About obsession. About the specific loneliness that addiction and obsession are both desperate, doomed attempts to fix, or anyway to not feel for a while.¹ And it works. DFW is the book, he's the person it's written about or for or whatever. He's an obsessive, was an obsessive, and you feel it in every over built footnote and every sentence that loops back to qualify itself one more time than itneeds to. The book is a manifetsation of the disease DFW had, rendered at a level of fidelity that should probably worry you a little, and does. ¹ Which is the saddest part, honestly: that the fixing never works, and the book knows it doesn't work, and goes on for a thousand pages anyway, the way you do.