Books: Anything by Iceberg Slim, starting with Pimp. It doesn't get much more real world than that. The Stand by Stephen King. He has an uncanny way of describing emotions that has helped me many times. Get him a subscription to MAD magazine. The kid will go a lot farther if he has a good sense of humor. As far as movies go, just make sure that he has seen Heat. No particular reason, it is just a kickass movie.