Newgrounds most definitely. And as an earlier poster stated, muds. Specifically MUME. Oh man many hours have been spent playing that game
Asklemmy
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BBS, ftpmail, archie, veronica, news, mail !! tons and tons of information never before available to me..
There was this guy on an old forum named "budsmoka" that once very shittily spray painted a cannabis leaf on his ps2
So many!
MS Comic Chat and their weird VR Chat, the former was always very lively and a great introduction to the world of IRC, the latter was just experimental and trippy.
Usenet and finding lively discussion, flamewars and so much porn and spam under one roof.
Instant Messengers like ICQ and AIM being the lifeblood of the social world.
I think the thing I miss the most is that there was so much to discover and discovering it was very much a word of mouth thing, you had to find links from friends, follow webrings and pointers from sites that made it onto Altavista and Yahoo (or astalavista for the less legit stuff), now everything is consolidated onto a handful of platforms, it feels less open than ever.
astalavista
Oh my god - I'd completely forgotten about that place! I just checked and it's stil alive: https://astalavista.box.sk/search/
I remember it being dark blue when I used it back in the 90s though.
"You got mail"
The owner of a site called zug dot com wrote a lengthy and hilarious essay on his treatment for an anal fissure. There were MS Paint illustrations of the procedure.
I was enthralled but also learned a lot about using humor to discuss situations that a person would otherwise be ashamed of.
Downloading a file and after hours of downloading it gets stuck at 99%
Definitely Chatrooms π
Earliest thing I remember was, as a kid of maybe 6 or 7, my family got internet installed (circa 95/96), and I found an early PokΓ©mon fansite (via Yahooligans, most likely) that listed all 150 PokΓ©mon and the "meaning" of their names (ie Hitmonchan and Hitmonlee are combinations of "hit" and Jackie Chan and Bruce Lee respectively). I was of course only just learning to read, so it took me a few visits to the website to read though every entry, but I was so stoked to see such engaging content on this new "internet"-thing
I wasn't born back then, but it would have been the fact that search results weren't total crap like today: only reddit seems to offer decent results if you don't want sites like wikihow to come up... I wrote a more elaborate blogpost partly about it.
I was a big MST3k fan back in the day. When it was on Sci-Fi, they had a MST3k-themed site called "Caption This" where it took screengrabs of whatever was on the channel at the time and you'd crack jokes about it.
It doesn't sound that interesting now, but if you're familiar with the show you'd see the appeal.
Also having to wait five minutes for a single JPEG of boobs to show up. Really helped teach a person patience.
The AOL kids home page with all flash games. I played a lot of the tom and Jerry blueprint game.
BonziBuddy destroying the family computer.
It's not that early, but eyezmaze.com (which apparently still exists) was one of those sites I found one day and regularly played on for years.
If you want to get a feeling of the old internet, look here: https://search.marginalia.nu/explore/random
To be clear, those are not (only) old sites, but a lot of them feel like the old web.
Eyezmaze β€οΈ
When there were dedicated websites to silly gimmick/songs like Hamster Dance, Boogie Blocks, etc.
Creating my own Proboards message boards and discovering Alien Adoption Agency.