Australian satirist, writer and graphic designer David Thorne got famous off an "email exchange" where he attempted to pay an overdue bill using a picture of a 7-legged spider. He is relentless yet somehow polite in his idiot-bashing; in other words he will keep going with inane gibberish and subtle insults, but ultimately wait for the other side to get heated and act like the moron he expects them to be. There is some questionable material on his site, and it seems that he really despises cats, but he has a way of humorously expressing what so many of us feel when faced with stupid questions, requests or situations - and he is genuinely funny and creative, not just a smart-ass.
Here is an example of his sense of humor...but you really have to go to his site and get sucked in for yourself. Take a look: