As for games, in the 80s, no one knew what worked or didn't work as far as computer games went, so everybody was pretty much throwing everything against the wall and seeing what stuck. And you ended up with some memorable games [1][2]. But over time, people learn, genres develop, budgets rise and you get less original and more homogeneous games.
It's the same with the web. When it went big in 1994, no one knew what they were doing, so everybody was pretty much throwing everything against the wall and seeing what stuck. But over time, people learn, genres develop, budgets rise and you get less original and more homogeneous pages, only this time with so many ads that it takes 500 requests to download your typical page these days.
What I think people are missing is this original, outrageous and anything goes type of experience. But I suspect the Cambrian explosion of web expression is dead for the time being.
[1] Qix (https://en.wikipedia.org/wiki/Qix). An abstract game that was mainstream and quite popular at the time. Haven't seen much like it sense.
[2] "The Earth Dies Screaming", a game I've never seen but the name alone is so evocative that I still remember it to this day. I think it was in the "alien invasion" genre popular back then.