Bruce Sterling's book The Hacker Crackdown (THC) captures the spirit and history of the "hacker scene" in the late 1980s and early 1990s. Having lived through that period with my C-64 and first 386 PC, I thought the author accurately describes what it was like for computer users during that era. THC is one of my favorite books on hacker activity because it combines a narrative with the author's accounts of interactions with key individuals. THC expertly tells several stories from multiple perspectives -- hacker, law enforcement, security professional, telecom operator, even homeless man-on-the-street! The author also manages to not offend technically-minded readers while describing material for non-technical audiences.
I found the last line of the book to be especially prescient: "It is the End of the Amateurs." This statement applies to offensive as well as defensive players in digital security. Consider the focus of THC: the hunt by law enforcement officials for, essentially, bit players in the digital underground. The offenders were basically joyriders (who no doubt caused plenty of headaches for security professionals) who didn't materially profit from their actions. The offenders also did not serve foreign masters for purposes of espionage. On the other side, many of the defenders were only discovering digital crime and pioneering incident response tradecraft in the heat of battle. In brief, THC is about amateur offenders vs amateur defenders. For the last five to ten years, digital security has been almost strictly a matter of professional offenders (criminal and state-sponsored) vs professional defenders (corporate, military, and improved law enforcement).
The bottom line is that anyone involved with digital security will enjoy reading The Hacker Crackdown.