Not a book but the novella “the machine stops” by E. M. Forster. I read this in the late nineties and it still pops up in my head frequently — especially in our age of the internet.
I found E M Forster’s novella “The Machine Stops” in the same league as the above: it is about the human condition, and technology is just a setup to talk about that.
An aside: the title is a great example of context sensitivity. On first glance, I interpreted the title as some serious bug in garbage collection algorithms/Systems (as in, they open some library that was an abandonware).