It's made with an old MS Comic Chat program that more or less acted like an IRC channel with cartoons, and was very buggy. If you look up Jerkcity on wikipedia, it'll have a link to an article about the program used.
I personally think the comic is hilarious. Why? I'm not entirely sure. I'm pretty sure a lot of it has to do with stock facial expressions that are usually out of place for what's being said. (
expample that I find particularly funny)
Brilliant? No. Funny, yes. Why, don't know. Maybe it's just the absurdity of dicklicking jokes in general.