1) Antifragile by Taleb (Skin in the Game is so far excellent as well)
2) The Border Trilogy by McCarthy
3) The Brothers Karamazov by Dostoevsky
4) East of Eden by Steinbeck
5) Slaughterhouse Five by Vonnegut
Taleb's books are something I almost hate to recommend.
I don't like a lot of his attitude (arrogance) and I'm not sure I'd call them all that well written either. He likes to ramble and seems to cram as many "SAT words" as possible into his writing, even when simpler/more commonly used words would done the job just as well.
With that said, they're some of the books that have made me reconsider the world around me the most and he has a very interesting take on the world.
1) Antifragile by Taleb (Skin in the Game is so far excellent as well) 2) The Border Trilogy by McCarthy 3) The Brothers Karamazov by Dostoevsky 4) East of Eden by Steinbeck 5) Slaughterhouse Five by Vonnegut