While scouring the internet for a Bomberman clone that supports multiplayer over TCP/IP, I found this piece still surviving from the distant past: the XBlast club from Boston's NEU.
While this isn't close to the oldest content I've seen (the oldest message in Google groups takes the cake there), I think it comes close to the oldest web page I've accessed directly. Cripes, it even uses the blink tag!
It's amazing how content has a knack of staying around long after its used-by date. Unfortunately, it often seems like the least useful content has the best chance of surviving. I imagine many pages have been lost that would be far more useful than the The XBlast Hall of Champions. (No offense to Carmine, Chris, Dave, Eric or Jeff.)
In a similar vein, Maciej Cegłowski's audioblogging manifesto rang true for me. Video and audio serve well for entertainment, but not really for publishing content that you want to be available in ten, a hundred or a thousand years' time.
I wonder what anthropologists will do in a thousand years to research the period around AD 2000? Search archive.org?