Edit: Amazon informs me that I purchased it on 19 June 2000.
This is probably not going to be popular, but "If liberty means anything at all it means the right to tell people what they do not want to hear."
by Neal Stephenson
It's very dated, but I have yet to find a single book (or essay for that matter) that gives a quasi-outsider's view of an industry that the public is apathetic to understand. The insights and descriptions are spot-on, even though the conditions have dramaticly changed over time.