Newgrounds most definitely. And as an earlier poster stated, muds. Specifically MUME. Oh man many hours have been spent playing that game
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Discovering that Burning Man exists. I'd never heard of it until I followed a link from Boing Boing and my head exploded.
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.
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%
I remember buying a very specific blacksmith vise from someone on a forum where I spent a lot of time.
I never really discussed with herb specifically on this forum except to arrange the sale but when I met her it was like meeting a friend.
She was in a meet with other people from this forum the week before, she told me about the projects they had and gave me extra pieces of exotic wood and Damascus steel that she made with another member for me to work with.
We didn't knew each other at all be the fact that we belonged to the same online community was enough for us to be instantly friend.
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
My dad trying and failing to dial out and connect to AOL italia to send his sister an email. I have no idea how much he paid for the service and the fact that local calls still cost money and I'm not even sure AOL was local, but it was so slow it took forever to send anything. Forget pictures.
Probably that happy zing you got whenever anyone signed your guestbook on your homepage.
Creating my own Proboards message boards and discovering Alien Adoption Agency.
The AOL kids home page with all flash games. I played a lot of the tom and Jerry blueprint game.
Probably watching an old Ed Edd N Eddy fan animation I found on yt that I cannot find a trace of anymore, or just the old yt shit post videos in general. That, or things like getting on Nitrome or any other site to play flash games. Mutiny on Nitrome was one of my absolute favorite flash games and one I never beat since I was still young.
The "download complete" Godzilla roar using the GoZilla! download manager. And using WinAmp to play my newly downloaded mp3's.
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.
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
BonziBuddy destroying the family computer.
When there were dedicated websites to silly gimmick/songs like Hamster Dance, Boogie Blocks, etc.
Green N logo. Windows 98. Teal solid wallpaper. Waiting for gifs to load and files to download on a 56k. BEEP BOOP. The burning smell of a CRT.
Bonus: emulating Metal Slug 5 on emulator
I fondly remember spending hours and hours in the T-Online BTX, which looked something like this: https://www.spiegel.de/fotostrecke/btx-jubilaeum-so-sah-der-internet-vorlaeufer-aus-fotostrecke-34503.html
There was this chat "village" themed based around Asterix & Obelix. I think it was the first chat I ever used, so it was magical. My older sister would mostly chat, while I watched. I still remember her handle from back then: Gutemine.
We later found out the chat cost 5ct/min (or 5 Pfennig per minute?)
The dancing Spider-Man gif.