The Simpsons: 10 Springfield Characters You Totally Forgot Existed
6. Leopold
With the exception of the infamous 'The Principal and the Pauper', Seymour Skinner has been one of the most consistently great characters in Simpsons history, made all the funnier by his relationships with his mother, Edna Krabappel, and Superintendent Chalmers.
The latter is possibly the most entertaining, and while everyone knows about their dynamic, it would be easy to forget that there is actually a character in between them in the elementary school chain of command. He may have only appeared in a handful of episodes, but Chalmers has an assistant called Leopold who he has sent to Springfield Elementary a couple of times in his place.
The huge, intimidating man who freely and openly calls the children he works with freaks has been there to introduce both Ned Flanders as the new principal, and Marge as the new 4th grade teacher.
He has since turned up in the background more times throughout the years. He was a member of the Stonecutters, was part of the crowd trying to get gum out of Lisa's hair in '22 Short Films About Springfield', and can be seen waving the American flag during a concert in season 15's 'Simple Simpson'.