"To have and have not" - Hemingway - I think Hemingway's Key West days were clearly his best and I think this story is particularly dark, but I'm a huge Hemingway fan.
"Guns Germs and Steel" - Jered Diamond - History is fascinating and i think it's cool to hear one person's thoughts on why some civilizations flourished and some died out.
"Searching for the Sound" - Phil Lesh - I love the Dead.