There's a "classic web" search engine / indexer / randomiser at https://wiby.me/; I put the 'surprise me' link on my bookmarks bar for a random peek into the classic web.

I just hit it though, and some are... kinda sad. Ended up here [0] and the last post from '03 seemed like the author was the last person that still checked in, they seemed quite dejected and sad. Looking further, their about page mentions them going to Rochester Institute of Technology to become an animator, and them being referenced a few times online as someone that was inspiring but who left the community / communities a while ago.

[0] http://aido.furvect.com/main.htm