First appearance: “Whacking Day” (Season 4, Episode 12)
Notable appearance: “22 Short Films About Springfield” (Season 7, Episode 21)
Voiced by: Hank Azaria

There's no man more frustrated with his job in Springfield than Superintendent Chalmers, or Super Nintendo Chalmers, as Ralph likes to put it. His frequent run-ins with Principal Skinner, Edna Krabappel, and Bart have solidified his legacy as one of the show’s great supporting characters. His charm ultimately lies in his being one of the few normal characters on the show. He’s just an ordinary man out to do his job, yet he’s constantly beaten down by the incompetence of the people surrounding him.

Chalmers is the ultimate straight man of this duo, and his exasperation with the over-extended Principal Skinner almost always boil over until Chalmer is screaming “Skinerrrr!” We have to hand it to Hank Azaria on this one for being able to make such real frustration a joy to listen to.