Lolcows are just an extension to my fascination with the darkness that lurks in the human mind, to me. I've been fascinated with this sort of thing since I was at least a teenager. I'm not entirely sure why I wanted to know what was going on in these dark minds, I'm not even sure if seeing one thing in a movie my dad watched or a game I may have played triggered my fascination with the dark side of humanity, but to this day whenever I'm looking at things about serial killers, child molesters, or even lolcows and shuddercows, I wonder to myself what goes on in their heads. Equal parts morbid curiosity and wondering what ED had to say at the time I'd first seen the site had me sifting through it and seeing what shit they had to say about things I liked or the drama related to them. Eventually a faked Doom screenshot pointed me to the page for OPL, followed by watching the CWCki and the associated forums for anything he might do next and learning about some pretty lulzy and fucked up people in the process, like ADF, Nick Bate, NephilimFree, Golden Knight, etc.
tl;dr: A mix of morbid fascination and Schadenfreude.