For me the high point was Fark or maybe Homestar and the low point was obviosuly Facebook... or maybe the end of Democracy.
Let's change that here and now! :)
I was one of the optimists in the very early 2000s when I attended a talk by Columbia professor Eli Noam. In 2002, he wrote an article in the Financial Times called "Why the internet is bad for democracy" which essentially predicted the world is we know it.
I immediately saw that he was right, at least with regard to the fact that it COULD turn out as it has, in fact, turned out. He fundamentally changed my view, way back then. In 2005 a version was published in a more academic context: “Why the Internet is bad for democracy.” Communications of the ACM 48(10): 57–58 (2005).
Here's the FT version: https://www.citicolumbia.org/wp-content/uploads/2022/01/Why-...
BTW the statement about democracy is not a lie - everyone knows some big and small revolutions happened after someone's post in social networks. Also such things as anonymous news sources, torrents and bitcoin has democraticized a whole lot of things in our lives.
History repeats
Voting as we have it, is a highly abstract, meta "democracy", with 'the will of the people' effecting a meaningless level of force on the tiller. As per the design.
"I beat the internet. The last guy was hard."