While Chris was technically my first lolcow I mostly learned about him via osmosis when he first got big on 4chan. Maddox was the reason I actually joined this site. The nigga with the funny articles now had his own podcast and that was only the tip of the faggotry iceberg. Maddox should have never appeared on TV much less started a YT channel. Bad ass balding whiny bitch pirate has a face for radio and a voice for print. And even then that schtick only worked because we thought he wasn't being serious.
The one sand only CWC. I tuned in during the Liquid Chris/Kacey saga, and that was some of the most hilarious shit I've ever seen on the internet. An underrated gem is the Chris/Kaceys father phone call, where her dad keeps calling him naive, and you could feel Chris' optimism fade away.
Back in Geocities heyday there were already pages existent that acted as a proto-tumblr. Already in them olden times there were folk talking bullshit like having headmates. My first consisted of these interlinked communities of crazy people.
Nugget is a 13 year old girl over 20 year old (thanks arghovaprinciples) autist artist pedofag on Deviantart who has a rabid fanbase and makes low-rate fetish art using MSPaint (LITTLE GIRL INFLASHIUN ONLY!!1!).
If you even DARE criticize her, she will kill you!
CWC was the first "official" cow, but I had seen others like Spax, Mariotehplumber, Guptill89, and the youtube commentary community circa 2008-2013. Mainly guys like Ely, Youngbloodfantasy, TOGproffessor, MrSirRaven, and Blackbustercritic. All of them are and were pretty lulzy.
Chris, Snapesnogger, and Applemilk1988. I remember a couple others, like Sephirothslave, this lady who would talk about how she was married to Sephiroth from FFVII in the astral plane, and Summoner Yuna, who also concocted a weird delusion about being married to Sephiroth.
I was reading a cached version of the Summoner Yuna page and found this:
Mine was probably Chad Himmelspatch, this would have been around 2001
This was a teenager (we all were, I would have been a tween) who was in the flash stick-death cartoon community, where he would just straight up steal peoples swf files and post them everywhere as his own. Soon Rob DenBleyker and Dave McElfatrick (cocreators of Cyanide and Happiness who were high school kids smoking pot and drunk puking in their shoes at the time) gathered a team of people to just mock him relentless in cartoon form, culminating in a pretty popular Flash megacollaboration called the Anti-Chad. It was... very primitive, and it didn't last long, but there were a few months to a year where it was pretty lulzy.
Whitney Way Thore was mine. Her antics on My Big Fat Fabulous Life were very entertaining and I’d watch episodes of it with my then boyfriend (now husband). Sadly, she hasn’t produced much m1lk lately, so I mostly watch cows like Tess Holiday and Amberlynn now.