Late 90s/early 2000s when there were tons of smaller isps offering a variety of solutions. This was back when operating a CLEC was a viable option before the incumbents found a way to fix that issue.
I think when the cable companies started monopolizing the internet and the web because commercialized, that's when we lost a lot of computing's early "innocence".
I'm sure someone will say I'm romanticizing that period, but darnit, just let me.