Leopold
Leopold is Superintendent Chalmers' assistant. He is a large, surly, snarling man with a balding head, bushy eyebrows, and a very stern-looking face. He wears a red suit and often speaks in a very aggressive, angry manner. When Principal Skinner had to be replaced, Leopold stomped in, issued several threats, horrified children by making them think he was the replacement, and then suddenly politely introduced the actual substitute, Ned Flanders. The children then collectively sighed with relief. The gag was repeated when Marge Simpson became a substitute teacher when the teachers go on strike.
Behind the Laughter[]
- His voice, intimidating attitude, and even parts of his physical appearance resemble that of renowned Clint Eastwood character Dirty Harry.
- He is one of the few characters on The Simpsons to have eyebrows.
- A similar gag was used in "Mayored to the Mob" when Leavelle starts berating his students, and makes it seem as though his students are going to fail his academy, he then suddenly tells them that they've graduated from his class.
- He appears in The Simpsons: Tapped Out as a limited time premium character for the Rommelwood Academy 2017 event and players can get him upon the completion of the Enriched Learning Center for Gifted Children which comes with him. He later appeared in a 2018 event.
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