Films: I'm not sure how well they'd go down now but "Ferris Buellers Day Off" "Weird Science" and "Easy Rider" did it for me. Books: One by Richard Bach, he's a bit sentimental but some of his ideas are great. Terry Pratchetts Thief of Time and Johnny and the Dead helped me put some order to what happens next.
Have you read Lord of the Flies by William Golding? I'd recommend that, its about young boys marooned on a desert island and basically the loss of their innocence. great book