Gary Chalmers

The Superintendent of the Springfield School District and Skinner's superior. He is the person Skinner fears most. Whenever he appears at the school, Skinner frantically invents lies to hide the chaotic state of affairs. Sometimes the two team up to boost the school's reputation, even operating under the joint name 'Chalmskinn.' Skinner addresses him as 'Superintendent,' while Chalmers calls him 'Seymour' or 'Skinner,' often shouting 'SKIN-NER!!' when angry. Though he used to just visit for inspections, he now appears so frequently he's practically a regular staff member. While they aren't on bad terms privately, he finds the principal's timid and groveling behavior in professional settings unreliable. He mostly spends his time monitoring Springfield Elementary looking for mistakes. However, he has shown concern for Skinner when they were in danger together. He is a survivalist and an avid homebrewer, a hobby he is surprisingly good at.

Willie

A Scottish illegal immigrant. He often harbors murderous intent or badmouths Principal Skinner. He is frequently seen wearing a kilt at events, much to the chagrin of others. Despite his appearance, he is incredibly muscular and has a habit of referring to himself in the third person. (Ten years ago, he was the swim coach until Skinner was trapped in a pool full of worms; Skinner then filled in the pool and demoted Willie to groundskeeper. He is a typical blue-collar worker—uneducated and hot-tempered—living in a shack behind the school.) He handles almost all manual labor at the school except for teaching and administration. He hates kids who make a mess and is easily fooled by their lies. His demotion happened because a troublemaker even worse than Bart, Andy Hamilton, filled the pool with worms and trapped Skinner there for a week. He also plays the bagpipes.

Otto

A long-haired hippie youth who works as the school bus driver. His driving skills are terrible, leading to numerous accidents and a wrecked bus. He is German-American, and Bart looks up to him like a big brother, usually calling him 'Otto-man.' He lives a lifestyle fueled by drugs and heavy metal.

Bart Simpson

The eldest son of the Simpson family, a 10-year-old boy who loves Krusty the Clown. He is a notorious prankster who has come close to expulsion many times. He is left-handed, struggles academically, and lives for mischief. He is a genius on a skateboard. He is the eternal rival and nemesis of Principal Skinner. He often says "Ay, caramba!" when surprised. While not as intellectual or morally driven as his sister Lisa, he is street-smart and quick-witted. He and Lisa call each other by their names. He has a shrimp allergy. Despite their constant bickering, he is a typical brother who secretly looks out for Lisa.

Lisa Simpson

An 8-year-old model student who wears a red tube dress and a white pearl necklace. She is an idealist with strong intellectual and moral convictions, though she possesses a delicate and sensitive side. She is a blonde, blue-eyed vegetarian. She is one of the few sane people in town and possesses one of the highest IQs in Springfield despite her young age. Her family includes Homer, Marge, Bart, and Maggie. She loves playing the saxophone and writing poetry.