My favorite "wild west" item from this time period is nineinchnails.net. I don't know who was running the site at the time, but they were ripping and hosting mp2/mp3 files of NIN's entire discography just out in the open and free.

A combination of limited hard drive space + sad dialup speeds prevented me from actually downloading the entire discog before the eventual shutdown in 98 or 99-ish.