- ―Superintendent Chalmers' catchphrase
- “Ow, my pelvis!”
- ―Superintendent Chalmers
Chalmers originally hails from Utica, New York, but has also said that he comes from Queens, New York, Mexico (in a deleted scene) and then moved to Intercourse, Pennsylvania. He attended Ball State University and is a proud owner of a red 1979 Honda Accord (and later, a Camry, which Otto Mann promptly wrecks). There is also some evidence that his main philosophy is liberal, from things such as his state of origin being New York (which is know for being a primarily liberal state) and some of the decisions he's made in his job, specifically when he fired Ned for introducing prayer to school. In the episode How The Test Was Won, Seymour Skinner mentions that Chalmers has a daughter. The episode What to Expect When Bart's Expecting revealed that Shauna Chalmers is his daughter.
Chalmers is a temperamental and whimsical man unfortunately vested with authority. His mood abruptly swings, and he seemingly-arbitrarily plays favorites: while constantly having little to no tolerance for Principal Skinner's well-intentioned mistakes, he shows apathy and dismissiveness of Ned Flanders's absolute non-disciplinarianism during his brief tenure as principal. It appears his only reason for constant hostility towards Principal Skinner is that Skinner "really bugs him". 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 "SKINNERRRRR!!!" or "SEYMOUR!!!", to which Seymour stammers, "S-Superintendent Chalmers!" His catchphrase has caused some paranoia in Skinner. On a few occasions, he says Skinner's name (or in one case, words pronounced similarly to "Skinner" such as "Skimmers") this way when absolutely nothing has gone wrong, implying that he either pronounces Skinner's name this way by habit, or does it on purpose to scare him. Chalmers has shown a caring side towards Skinner, when he called out for Skinner and when he had a reply that Skinner was okay, he told Skinner to "Never do that again" (scare him).
Chalmers's own competence and dedication to his job are questionable. He let Ned Flanders allow the school to descend into anarchy when he was principal, freely admitting that he had fired Skinner for far less, explaining simply that "Skinner really bugged me." In fact, the only reason Chalmers even allowed Skinner to be reinstated as Principal that time was because Ned Flanders introduced prayer into the school (because Chalmers feels that religion should never be placed within school walls, just as facts don't have a place within an organized religion). When asked about Skinner's reinstatement, he said simply, "Ehh, he seems to know the students's names. " Another example being when he had to deal with an angry mob of women after Skinner made a statement that came off extremely gender biased against women. So to fix it, Chalmers replaced Skinner with a female principal who was undeniably even more gender bias with her first order of business being the segregation of male and female students. Chalmers seems disturbingly unconcerned with the school's decline, saying that "the way America's public schools are sliding, they'll all be like this in a matter of months. I say enjoy it — it's a hell of a toboggan ride!" He also promotes people based on personal bias as opposed to actual competence, promoting Principal Holloway, described by Skinner as a "drunk" and Chalmers as a "pill-popper," to assistant superintendent, overlooking the efforts made by Skinner to improve his school's standing. Ralph called him Super Nintendo Chalmers, which he makes a confused facial expression at. He says anything that ends with inner or nner, he would raise his tone, he once said "Stupid fish, don't you want to be my DINNERRRR!!!?"
Chalmers was at one point a high school teacher, but was put off the profession after he was beaten up by the fight club thinking it was the "breakfast club." He was coerced back into teaching for a short while years later, taking Bart Simpson under his wing and managing to get through to the boy where others had failed.
When Springfield began erecting surveillance cameras around Springfield and 742 Evergreen Terrace is discovered to be a blind spot and transformed into a crowding place for rebellious activity, Superintendent Chalmers was spotted swinging nun chucks while prancing in a tutu.
Chalmers was seen dating Agnes Skinner, much to Seymour's dismay,  although in other episodes he has mentioned he is married. In "Bart Stops to Smell the Roosevelts" it is revealed that he is divorced.
In Homer Goes to Prep School it's shown that he's a member of the Doomsday Preppers (People who believe society will collapse at any moment). His basement is filled with food and other supplies needed to survive the end of society. When Lloyd said that they shouldn't look at the faces of people who didn't prepare, Chalmers shows them a solution to the problem: A rifle scope that makes any human face look dangerous and threatening (by placing angry eyebrows on their faces). Near the end of the episode when Lloyd mentions that in the new world he'd be a big shot, Chalmers said he and the others were planning to seal him in a cave. When Lloyd said he was going to poison their drinking water, Chalmers said he'll drink his own urine.
In the episode "Future-Drama", which takes place in the future, the Superintendent is practically a vegetable, only capable of saying his trademark line. In the episode "Holidays of Future Passed, Superintendent Chalmers is shown to be frozen in the Springfield Cryogenic Facility, along with other elderly characters.
In a Simpsons Comic he states that he went to LSU.
Chalmers appears in The Simpsons Game walking around the Towns Sqaure with Lenny, Krusty, Charlie, Dr. Hibbert and Kent Brockman. Later when the Aliens arrive in Springfield, Chalmers tells Edna the end may be upon them. Edna agrees and says they should roll around in the hay before they die. Chalmers refuses Edna then says If Seymour ever found out he would be devastated Chalmers then agreed to roll around in hay with Edna.
In the DVD commentary to "22 Short Films About Springfield", Simpsons creators noted that Superintendent Chalmers seems to be one of the few "normal" characters on the show, and Chalmers is frequently alone in his awareness of the show's zaniness.
- His first name was revealed to be Gary in Yokel Chords.
- His hero is Theodore Roosevelt.
- Edna and Chalmers were once caught "doing it".
- Ralph Wiggum addresses him as Super Nintendo Chalmers.
- His surname 'Chalmers' is of Scottish origin, hinting that he is of such descent.
- ↑ 24 Minutes
- ↑ "Bart Stops to Smell the Roosevelts
- ↑ "What to Expect When Bart's Expecting"
- ↑ 22 Short Films About Springfield
- ↑ The Old Man and the "C" Student
- ↑ Lisa's Date with Density
- ↑ Homer and Lisa Exchange Cross Words
- ↑ The Debarted
- ↑ Sweet Seymour Skinner's Baadasssss Song
- ↑ Whacking Day
- ↑ Lisa Gets an "A"
- ↑ Bart Stops to Smell the Roosevelts
- ↑ To Surveil With Love
- ↑ Bart the Fink
- ↑ The Heartbroke Kid
- ↑ How Munched Is That Birdie in the Window?