Take the jargon file for a spin. So much history in bite-sized pieces masquerading as a dictionary. Check out the recommended reading list at the very bottom of the file. (There are HTML versions of the jargon file available but, for the real experience, it must be read fixed-width, 80 columns on a green screen.)
Hackers: Heroes of the Computer Revolution is a must-read (along with Cuckoo's Egg, previously mentioned.)
CYBERPUNK: Outlaws and Hackers on the Computer Frontier, another classic.
Except for the whole Global Thermonuclear War thing, War Games is a fairly accurate representation of 1980s technology. It's also a fun movie.
Folks are going to hate this but I don't care: 1995's Hackers. While technically suspect, it accurately depicts the personality traits of 90s hackers, had a great soundtrack and introduced me to Angelina Jolie ample acting skills.
https://www.amazon.ca/Cyberpunk-Outlaws-Hackers-Computer-Frontier/dp/0684818620
He's always come across as a bit of a dick, but he was clearly very good at what he did.
Cyberpunk is another good classic
Wargames is loosely based on him. There's a book called "Cyberpunk" that details some of his exploits.
http://www.amazon.com/CYBERPUNK-Outlaws-Hackers-Computer-Frontier/dp/0684818620
I read this book.