GameSpy and the planet network, especially thier hosting / match making systems. Maybe it was just being able to know a couple servers and run into the same people over and over, but I remember liking that a lot.
The Happy Puppy games site.
Not really the web, but the original RealPlayer surfaced some amazing content for the time. I was able to watch Russian news, which while I didn't understand a single word was pretty amazing for a cold war obsessed kid
I suspect the constraints made it better. You’d already dropped a small amount of money on the magazine, built up the anticipation of getting it home, and now you were definitely going to give the demo a good whirl.
Also, demos /shareware were an important marketing mechanism back then, companies took them seriously.
The Happy Puppy games site.
Not really the web, but the original RealPlayer surfaced some amazing content for the time. I was able to watch Russian news, which while I didn't understand a single word was pretty amazing for a cold war obsessed kid