Leopold, voiced by Dan Castellaneta, is Superintendent Chalmers' assistant. He is a large, surly, snarling man who frequently speaks through clenched teeth, and is one of the few characters on The Simpsons to have eyebrows. When Principal Skinner has to be temporarily replaced, Leopold stomps in, issues several threats, and terrifies the children by making them think he is the replacement, and then suddenly politely introduces the actual substitute, Ned Flanders. The children then collectively sigh with relief. The gag was repeated when Marge Simpson becomes a substitute teacher in the episode "The PTA Disbands". Leopold often refers to the children of Springfield Elementary as "little freaks."
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