Rereading the Internet classics

As we all know, context is everything. With that in mind, I have embarked on a journey to reread some of the classics that portended the future, and some that missed it. I'm mostly wanting to see how I might interpret things differently given all that has transpired over the last few years.

Of course, a classic measured in Internet Years is not a very old book. Right now I'm reading David Weinberger's Small Pieces Loosely Joined. It was published in April 2002, which means with print publishing cycles being what they are, that it was written around the turn of the last century. I'm working my hardest to make it sound really, really old.

What is making it such an interesting reread is that it was written pre-Wikipedia. Is that an accurate demarcation point for defining a classic? Is that the earliest and most knowable point in time that people can relate to looking back? When the world as we had known it changed forever? Now, I know that this could make an interesting discussion in itself, but I need to invoke my age here and mention that I first started using CSNET in 1983. I was teaching about the Web before it was graphical, and yes I remember exactly where I was the first time I saw Mosaic. I have been around to see most of this unfurl, and I'm thinking 2002-2003 is around the time when we started to see some really profound societal changes. So I ask the question, does pre-Wikipedia work for defining a classic?
Anyway, here are the other books on my immediate reread list:

• Being Digital by Nicholas Negroponte, 1995.
• Life on the Screen: Identity in the Age of the Internet by Sherry Turkle, 1995.
• Business @ the Speed of Thought: Succeeding in the Digital Economy by Bill Gates, 2000. (hehe)
• The Hacker Ethic by Pekka Himanen, 2001.
• The Future of Ideas: The Fate of the Commons in a Connected World by Lawrence Lessing, 2001.

This is not meant to be a list of the "the classics"-- if it were it would be a very different list, although a couple of these would most definitely qualify. These are simply the books on my bookshelf that I'm thinking deserve another look. I'm curious what might be on your shelf that you deem worthy of a reread?