Since we're defining vintage as pre-2007 (presumably due to CWC's discovery and the rise of social media) I suppose I will list my favorite vintage lolcows of the Web 1.0/Web 1.5 era.
For clarity's sake, I consider Web 1.0 to be the internet in the 1990's and the very beginning of the 2000's (2000-2001) with Web 1.5 being the internet from 2001-2008, after 9/11 and the Dot Com bubble bursting but before the Great Recession and Web 2.0.
Basically, if Web 1.0 was the days of Usenet, Geocities, and AOL, then Web 1.5 were the days of Myspace, YTMND, LiveJournal, early YouTube, and the "wild west" era of 4chan.
The best vintage cows in my opinion were Jack Chick, Usagi Kou, David Gonterman, and The Final Fantasy House.
The weirdest part is that Gonterman is the only one who actually mellowed out and truly quit being a lolcow, or at least stopped providing material for the trolls.
Jack Chick is dead but he has a backlog of unpublished tracts similar to the backlog of Tupac songs, plus the guy who succeeded him at Chick Publications is likely to be a lolcow in his own right as well.
Jennifer Cornet may no longer be a Final Fantasy fan, but she's still running her fandom cults somewhere, with the Hannibal Cult and the Tattlecrime debacle being a relatively recent one and the most notable one after the infamous Final Fantasy House.
Usagi Kou was a classic Web 1.5 lolcow of the early 2000's and mid-2000's and then the trail went cold and more prominent lolcows like Chris, Pixyteri, ADF, and many others came along.
But it turns out Usagi was still very much as active and insane as she was back in the day.
Now she's resurfaced in a major way with her anorexia, self-harm, and her battered husband who is a decade younger than she is.
I'm curious about how many Web 1.5 lolcows are still around but have been forgotten, and I'd like to see more people dig up arcbives of old drama for the newer Kiwis and for those interested in lolcow history without having to deal with ED and its unique idiosyncrasies.
There's more remnants and relics of Web 1.5 than Web 1.0 and I think it was more fertile ground for online insanity simply because the Internet back in the 2000's was a lot easier to access than it was in the 90's but was also less consolidated, curated, corporate, and censored like it is in the 2010's.