Discovering that Burning Man exists. I'd never heard of it until I followed a link from Boing Boing and my head exploded.
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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.
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%
Probably that happy zing you got whenever anyone signed your guestbook on your homepage.
BBS, ftpmail, archie, veronica, news, mail !! tons and tons of information never before available to me..
Having my own email address, making a website and pirating a metal album
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.
My first Internet connection was based on GPRS and I remember images taking ages to load and loading in chunks. Moreover the connection kept interfering with the surround audio system and sometimes I would hear noises similar to the dial up modems.
I also remember the first times I tried using eMule (is it still up and running?): I was searching for the video song "Elevation" by U2 but I was unaware of rule 34; you can imagine what I actually downloaded.
There was this guy on an old forum named "budsmoka" that once very shittily spray painted a cannabis leaf on his ps2
The AOL kids home page with all flash games. I played a lot of the tom and Jerry blueprint game.
Newgrounds most definitely. And as an earlier poster stated, muds. Specifically MUME. Oh man many hours have been spent playing that game
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 โค๏ธ
Staying up till 2am to play BRE (Baron Realms Elite) on a local BBS. 2am because that was a time I could dial in without the line being busy.
I also played a little LORD (Legend of the Red Dragon), but BRE was my favorite.
BonziBuddy destroying the family computer.
When there were dedicated websites to silly gimmick/songs like Hamster Dance, Boogie Blocks, etc.
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.
"You got mail"
Creating my own Proboards message boards and discovering Alien Adoption Agency.
friv.com
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?)
Going to an internet cafรฉ, filling a CD-R to the brim with whatever I could fetch in 1 hour, and enjoying whatever I brought on my very offline home computer for the next week