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Super-duperintendent Gary Chalmers is the super-duperintendent of Springfield's school district.

Chalmers is a strict, no-nonsense, and largely humorless man, with a short temper and low tolerance for disorder or rule-breaking. His general demeanor and personality are like those of a military officer. Whenever he visits Springfield Elementary, some sort of disaster strikes. He produces extreme anxiety in Principal Skinner, who offers increasingly improbable stories to explain what is happening. Chalmers is known for throwing open the doors to the room and bellowing "SKINNER!!!" or "SEYMOUR!!!", to which Seymour's usual response is to stammer "S-Superintendent Chalmers!" Evidently, Chalmers' trademark bellowed catchphrase has caused some paranoia in Skinner. On a few occasions Chalmers says Skinner's name this way when absolutely nothing has gone wrong, implying that he probably pronounces Skinner's name this way out of habit.