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[]
- 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.
Gallery[]
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Appearances[]
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
- Episode – "Homer's Adventures Through the Windshield Glass" (couch gag)
- Episode – "AE Bonny Romance"
- 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
| The Simpsons: Season Five | ||||
| "Homer's Barbershop Quartet": | "Cape Feare": | "Homer Goes to College": | "Rosebud": | "Treehouse of Horror IV": |
| Absent | Absent | Absent | Absent | Absent |
| "Marge on the Lam": | "Bart's Inner Child": | "Boy-Scoutz 'n the Hood": | "The Last Temptation of Homer": | "$pringfield (Or, How I Learned to Stop Worrying and Love Legalized Gambling)": |
| Absent | Absent | Absent | Absent | Absent |
| "Homer the Vigilante": | "Bart Gets Famous": | "Homer and Apu": | "Lisa vs. Malibu Stacy": | "Deep Space Homer": |
| Absent | Absent | Absent | Absent | Absent |
| "Homer Loves Flanders": | "Bart Gets an Elephant": | "Burns' Heir": | "Sweet Seymour Skinner's Baadasssss Song": | "The Boy Who Knew Too Much": |
| Absent | Absent | Absent | Minor | Absent |
| "Lady Bouvier's Lover": | "Secrets of a Successful Marriage": | |||
| Absent | Absent | |||
| The Simpsons: Season Six | ||||
| "Bart of Darkness": | "Lisa's Rival": | "Another Simpsons Clip Show": | "Itchy & Scratchy Land": | "Sideshow Bob Roberts": |
| Absent | Absent | Absent | Absent | Absent |
| "Treehouse of Horror V": | "Bart's Girlfriend": | "Lisa on Ice": | "Homer Badman": | "Grampa vs. Sexual Inadequacy": |
| Absent | Absent | Absent | Absent | Absent |
| "Fear of Flying": | "Homer the Great": | "And Maggie Makes Three": | "Bart's Comet": | "Homie the Clown": |
| Absent | Cameo | Absent | Absent | Absent |
| "Bart vs. Australia": | "Homer vs. Patty and Selma": | "A Star is Burns": | "Lisa's Wedding": | "Two Dozen and One Greyhounds": |
| Absent | Absent | Absent | Absent | Absent |
| "The PTA Disbands": | "'Round Springfield": | "The Springfield Connection": | "Lemon of Troy": | "Who Shot Mr. Burns? (Part One)": |
| Minor | Absent | Absent | Absent | Cameo |
| The Simpsons: Season Seven | ||||
| "Who Shot Mr. Burns? (Part Two)": | "Radioactive Man": | "Home Sweet Homediddly-Dum-Doodily": | "Bart Sells His Soul": | "Lisa the Vegetarian": |
| Absent | Absent | Absent | Absent | Absent |
| "Treehouse of Horror VI": | "King-Size Homer": | "Mother Simpson": | "Sideshow Bob's Last Gleaming": | "The Simpsons 138th Episode Spectacular": |
| Absent | Absent | Absent | Absent | Absent |
| "Marge Be Not Proud": | "Team Homer": | "Two Bad Neighbors": | "Scenes from the Class Struggle in Springfield": | "Bart the Fink": |
| Absent | Absent | Absent | Absent | Absent |
| "Lisa The Iconoclast": | "Homer The Smithers": | "The Day The Violence Died": | "A Fish Called Selma": | "Bart on the Road": |
| Absent | Absent | Absent | Absent | Absent |
| "22 Short Films About Springfield": | "Raging Abe Simpson and His Grumbling Grandson in "The Curse of the Flying Hellfish"": | "Much Apu About Nothing": | "Homerpalooza": | "Summer of 4 Ft. 2": |
| Cameo | Absent | Absent | Absent | Absent |