Outside of YouTube, the dawn of "weird web" for me is Homestar Runner [0], and Don Hertzfeldt's Rejected [1].
How did you watch it online, before it was (much later) put on YouTube? I feel like he didn't have a website at the time, but maybe it was that obvious? Were people sharing a video of it on file-sharing networks? (Honestly, I do feel like we knew it too well to not be watching it on loop, but I simply don't remember how we did it... all of my memories of Don's work--and honestly some of the short interstitials he did for the film festival are some of my favorites! "the illuuuussion of mooovement" ;P--are in a theatre.)
I am a consumer whore! And how!
My spoon is too big.
By the time I was in college in 2003, Don Hertzfeldt animations were all over the Internet (usually in truncated, uncredited form).
Don's new series, World of Tomorrow, is really great, btw, and a wonderful maturation and evolution of the animation style I saw in that GIF in 1998.
It hadn't occurred to me until just now, to wonder if that CD is still around, and if anyone ever archived it. I'll probably see my folks for the holidays and I'll try to remember to take a usb cd drive in case I can lay hands on the disc.
Later, Rejected showed up in Spike & Mike's animation festival, but I think I'd seen it passed around online by that time, and actually most of the stuff in the festival that year (probably 97?) was familiar. IRC Fservs were huge by then and they basically demolished the novelty of in-person festivals.
In a similar vein, the famous "Miss Teen South Carolina" stuck in my craw, and I often throw out a "like such as" when demonstrating something for humorous effect.
I guess these pop culture references really date me, but among my age group they get a laugh, for whatever that's worth.
September 2003, Badger Badger Badger: https://knowyourmeme.com/memes/badger-badger-badger
March 2002, Peanut Butter Jelly Time: https://knowyourmeme.com/memes/peanut-butter-jelly-time
August 1998, Hampster Dance: https://knowyourmeme.com/memes/hampster-dance
That site was the beginning of my love affair with all things weird and esoteric on the internet.
I got scroll buttons as the day is long.
for me it's "dag, yo"
and, whenever I see "Ontario": "On-tah-REE-oh, CAH-nah-da—ooh, a little south of the border flavor"
Perhaps more because H*R is a brainworm which refuses to leave :)
"...oh trevor, I pine for you!"
"..ohhh, there's TWO of them"
"how's it hangin, texas?"