Infinite Jest by David Foster Wallace

This book is epic, on the scale of something like Moby Dick or War and Peace or Ulysses. Various sub-plots, which involve the Ennet Drug Recovery House and the Enfield Tennis Academy (whose founder, James O. Incandenza, but known to his family as Himself, committed suicide by sticking his head in a microwave oven, after completing an entertainment known as Infinite Jest so compelling that it causes viewers to stop thinking about anything else while they view it), proliferate throughout the book. The version of the near future presented in the book is fun to entangle, bit by bit, so I'll avoid saying too much about the plot. I think it is fair to say that the novel presses on the conjunction of entertainment, pleasure, and communication, and examines how we connect with those around us. It's a bit of a challenge to get all the way through, but it repays the effort put into it.