I am reading @carlmalamud's "Exploring the Internet" (1992) and it's such a joy. Every chapter has a few gems.
I had no idea that already in 1991 @brewsterkahle's #WAIS was able to retrieve documents in response to queries in natural language. I remember librarians discussing how to add such functionality to their OPACs well into the 2010s.
https://archive.org/details/exploringinterne00mala/page/166/mode/2up