There was this guy on an old forum named "budsmoka" that once very shittily spray painted a cannabis leaf on his ps2
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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.
Downloading a file and after hours of downloading it gets stuck at 99%
Discovering that Burning Man exists. I'd never heard of it until I followed a link from Boing Boing and my head exploded.
Having my own email address, making a website and pirating a metal album
BBS, ftpmail, archie, veronica, news, mail !! tons and tons of information never before available to me..
AIM! My entire junior high would be up all night chatting away. I figured out my mom's password on her power Mac, and hid out in her office lol. It was so fun and novel at the time.
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
Probably that happy zing you got whenever anyone signed your guestbook on your homepage.
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.
Newgrounds most definitely. And as an earlier poster stated, muds. Specifically MUME. Oh man many hours have been spent playing that game
The AOL kids home page with all flash games. I played a lot of the tom and Jerry blueprint game.
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.
"You got mail"
The dancing Spider-Man gif.
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
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.
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.