I have a pet theory that much of what we're seeing culturally is that the 90s and early 2000s (at least in the US) was a window of time that offered a sense of safety and surplus. 9/11 was extremely culturally disruptive, but aside from that, for many in the US, it felt like there was "enough to go around". That environment breeds a lot of creativity, innovation, whimsy, and doing things for their own sake. But that…
This was not a natural evolution of the web but the consequence of low-tech people accessing the web passively via a tiny touchscreen.