I think there is good discussion to be had here, but holy shit , I have never been able to get over how utterly pretentious Jerry's writing is. The comics are usually fantastic and at strange odds with the accompanying news.
It's always been my understanding that he writes that way simply because he enjoys it, and he's perpetually incredulous that he can make a living doing so.
Generally when I read something and judge it to be pretentious, it's because the author is using words that are out of his/her depth, in an attempt to impress the reader. When Jerry writes I get the impression he's choosing his words carefully and with equal intent to entertain and to inform.