Leopold is Superintendent Chalmers' assistant. He is a large, surly, snarling man. 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
- 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.
- Episode – "Sweet Seymour Skinner's Baadasssss Song"
- Episode – "Homer the Great"
- Episode – "The PTA Disbands"
- Episode – "Who Shot Mr. Burns? (Part One)" (Seen at the Oil Appreciation Day)
- Episode – "22 Short Films About Springfield"
- Episode – "Simple Simpson"
- – The Simpsons Movie
- Comic book – Bart Simpson Comics 5 "Bart Simpson's Day Off"
- Comic book – Bart Simpson Comics 24 "Bart's Got Spirit!"
- Video game – The Simpsons: Tapped Out