Please go out and buy either "Waiting for Godot" or "Endgame" by Samuel Beckett. They're easily two of the most fascinating pieces of literature I've ever read/seen (they're both short plays).
The basic question of both plays is "what is existence?"
Bowling Alone is a good book. Don't let the title fool u. It's on the rise and fall of comunity in American society. Also check out Siddhartha. Fear and Loathing in Las Vegas is 100 times better than the lame ass movie.