Dolphy was probably my first. My friend who is a pretty big artist had been telling me about her for ages because she used to use DA (before it turned into a shit cess pool for spergs and pervs), and I followed her whole Jim Hawkins is my husbando saga, and watched as she cucked him for Jack Frost in recent months, the frigid bitch.
There used to be this insane fundie blogger who had 5 kids crammed into a tiny 2 bedroom apartment who raised her kids; on her illiterate husbands $1000 a month WalMart Janitors salary. Her husband as a lolcow as well, he was a bible college student who was borderline illitterate and had a hard time even spelling his own name. She refused to let her kids see doctors as well as herself instead paying for a midwife even though they received Medicaid benefits. She refused to use an oven because that costs too much money and instead cooked everything inside a crockpot. She made a big deal out of how she fed her kids healthily by not feeding them GMO's yet the majority of their meals appeared to be hot dogs, and cheap ground beef from the dollar store. She made her own "pasta" if you could call it that. The recipe for her pasta was water and flour which is the recipe used to make paper mache paste.. Eventually in the long term her plan was to buy land and have her family live in a Yurt.
Geez I had to think about this one for a little bit. As I have seen quite a bit of crazy online way back in the day but since I knew Dave Kelly back in 2000 that has to be the first, Though I was reading Lowtax articles back when he still worked for gamespy doing planetquake while Fragmaster ran planethalflife. Those two clowns really pushed the whole embarrassing online persona thing to make a buck before youtube and steaming were even concepts. Before that the closest thing you got were idiots on a forum or bbs board that would routinely embarrass themselves, especially in the gaming community.
Though I think the most memorable from that time period had to be https://encyclopediadramatica.se/Shay when it first got posted in 2005, just because it was so gross and it went downhill so fast with her dying from overdose food and going all Gilbert Grapes mom in the nut house.
Its crazy to think how little exposure these people had with only forums and later crude obscure outlets like livejournal and blogs to get their crazy out there. I think Dave really pioneered the whole Art Cow thing online by having a half dozen Keenspot comics at once, While still having time to be active in the emergent oekaki community. Taking after John Krotchfruitcake's Spumco where he had his public meltdown with Nickelodeon and subsequent churned out flops.
Spax3 for sure. I watched the whole drama unfold because I was a dumb kid, who liked his videos and subscribed to his channel. Even before he got his mummy to get children to try to stop bullying him I knew he was lolcow deep down, but I ignored because his videos were so "EPIC XD." I remember getting a few angry private messages from his fans/socks because I reposted his shitty Sonic X fandub. I really wish I saved them before the video got DMCA'd by Spax3 himself
He genuinely thought he was better than the voice actor who played Sonic. "DA Stars DA Moon."
He won several awards from alt.usenet.kooks (kind of a predecessor of Kiwi Farms) for, among other things, trying to sue several thousands of people for saying things about him that were 100% true but 100% unflattering, stinking up several newsgroups with his shit that they became completely unreadable, and just generally being a net.kook extraordinaire.
Once, when his postings became sparse and generally boring, I sent a 4 page letter to his mother (whom he was living with at the time) mentioning just some of the things that her 40-something son had been up to while living in her apartment, and that made him extremely entertaining for several weeks after. Looking back, that was kind of a dumb thing for me to do for several reasons, but it was amusing seeing him rant about it and come up with crazy theories about it to match his delusions.
He's still around, and on one of his Youtube videos he mentions that he gets SSDI due to COPD and being legally blind, which might explain why he can't see all the dust that's built up on the fans in the background of his videos.
Chris-chan is probably the first I actively knew of as a lolcow and followed, but before I knew of the term, my first real encounter with a lolcow was this kid who went by the username Dattebayo on the Serebiiforums. He was on the site since 2007, and everyone didn't like him since he proved himself to be an annoying little shit who also had creepy vibes and legit took advice from South Park (example of this here). He got banned several different times, and it would freak him out since supposedly Serebii was like a "refuge" for him or something.
After he terrorized the forums for a few months by using sock accounts that called themselves "Team Tee Hee" to harass people and send disgusting fetish (so he claimed) pictures to them (he made a thread confessing to his crimes here), the webmaster and admins actually had a meeting to figure out what to do about this situation. He used his autism for an excuse for why he did it, and this was the last straw for everyone. He was permabanned, and he just dropped from the face of the Internet.
Dattebayo's great lolcow material if he's still around, but after he was permabanned, I didn't try looking for him because "good riddance" and all that jazz. It's been several years since, and unless he's been incarcerated for CP or whatnot (because he has pedo tendencies, he still admitted to liking Dawn's feet up until his ban), I do believe he's elsewhere on the Internet still doing the same shit (I hope he had a massive chimpout or sperg-attack when Naruto ended), I just haven't found him again.
Jerry Peet, as he's the one who brought me to /cow/, and eventually here, where I got more into lolcow culture. But the FIRST lolcow before even knowing what the term meant was a Youtube user named "Meleemaster01", an apparently 14 year old girl on youtube who had a very small channel all of seven years ago (Jesus fucking Chris-Chan, I'm old) whose claim to fame is essentially plagiarism.
You might think that username is relatively normal, but the thing is, she "came up" with it after ripping it from another Youtube user named Brawlmaster08, a small channel, but popular within his community because everyone loved the rant videos he made (Yes, it was during a time when making rant videos on Cartoon Network and Nickelodeon was the 'cool' thing to do). But name-ripping is not what made her a lolcow, oh, no, no no no no. As one may expect, she called BM her inspiration and eventually started making videos - all of which copied BM's point-for-point, and occasionally word-for-word. What made it worse was that she simply could not take constructive criticism. BM called out MM once on video, which prompted all of his fans (he had a very active fanbase) to start sending :autism:-tier insults to her videos, mainly just calling her a ripoff.
I think the biggest irony is that some of BM's fans had no problem ripping points or jokes from BM himself. It was a very enjoyable time.
After about a day (or maybe even a few hours) BM apologized and told her to simply stop ripping off his videos. She accepted, and everything was well for a while... until she started ripping off videos again. This continued all throughout the summer of that year, until MM finally closed down her channel. A few hours later, a mysterious account opened, saying MM was their inspiration, and eventually started uploading directly ripped videos from other users within that community. The channel was evidently flamed to death, and they uploaded a video saying that they actually were MM, and that she actually wasn't a girl. She was an 11 year old boy pretending to be a 14 year old girl.
I only used she/her 1. because I'm used to using them to refer to MM and 2. because of shock value. Surprised by the ending? Heh.
There are lots of lolcows out there, but CWC is really the only one who is very memorable to me, not only because he was my first lolcow. Just the thought of a 30-year-old manchild who has had his entire life documented, ridiculed and analyzed amuses, confuses and interests me. The fact of how pathetic his life is and how he is constantly making it worse with everything he does is hilarious. And the fact that he puts it ALL online? Everyone can see it! It's kind of like watching an animal hunt itself. You want to feel sorry for it, but all of its wounds are self inflicted. That's why CWC is such a special person. The fact that your life can go so far south that you've essentially become a joke to every person you know fascinates me.