The early internet is a period I wasn't there for and yet am strangely nostalgic for regardless. It might be because it was for a short time truly a frontier were you could say whatever you wanted to say.
Nowadays forums like Kiwi are all that's left that preserve that concept. As most sites are censor heavy.
I'm a relic of those early years.
Have been active on various fora and BBs since 2001.
The environment was as you'd described - The average forum-goer back then was a lot more socially, psychologically or politically fringe - Which guaranteed that forums/BBs were quite eclectic. Long-form posts were more common then, too.
I have maintained for years that, with the ascent of social media, the robustness of those qualities began to experience attrition, due to the influx of 'normies'.
The increased popularity of the Internet and engagement from the mainstream has led to the situation we find ourselves in, IMHO. Up until perhaps 2008 to 2009, nobody
truly cared what a 'bunch of weirdos online' said about anything. When the Internet becomes more integrated with the real-world, things become more 'real' and less abstract or disconnected.
Truthfully, the Internet's prime was when it was mostly populated by dissidents, heterodox thinkers and other miscellany freaks. Oh well.
On topic, some of you may remember
Big-Boys.com, which was a male-centric video and image sharing site from the late 90s that popularized (and might have coined) a lot of the media tropes that still exist today (eg. 'fail' videos, 'This Week In' segments, rewarding users for their original uploads). The site was rebranded as
Break.com in the mid 00s from memory.
I'd say 40-50% of the content hosted there wouldn't be allowed on Youtube now - Plenty of politically incorrect videos, unabashed sharing of scantly clad women, obscene pranks etc.