Web nostalgia tends to focus on dull corporate sites and design evolution.
I set myself the challenge to excavate just the stupid internet that I actually spent my time browsing.
To do so, I scraped all the links featured in the DMOZ "Humor" category from the year 2000. I then ran a script to make sure that Wayback Machine has something from the 90s in their archive for each one. This left the remains of sites. Mostly awful.
I did the same for all the sites ever mentioned in Select Magazine for a more studenty selection. This database has links. A mix of the indie, the funny and the bizarre.
If you must share this on web 2.0 (ptooey), then click away.
Although I chose my sources in part because they had editors and thus some quality control, there's a chance of some dodgy stuff in the database. That said, it seems to be mostly Bill Clinton jokes, themed pun collections and irrelevent sites that the editors have mis-categorised. The Select links can be a bit more edgelordy, though are mostly fine. If anything is genuinely nasty, let me know and I'll remove it.