Leopold

Voiced by Dan Castellaneta, Leopold was Superintendent Chalmers' assistant. He was a surly, snarling one-trick pony; when Principal Skinner had to be temporarily replaced, Leopold stomped in, issued vague threats, and terrified the children, making them think he was the replacement, and then suddenly and politely introduced the actual substitute, Ned Flanders. The children then collectively sighed with relief. The skit was repeated when Marge Simpson became a substitute teacher in the episode The PTA Disbands.

The truth about Leopold (which the kids do not know) is that his bark is a lot worse than his bite.