- ―Superintendent Chalmers' catchphrase
- ―Superintendent Chalmers' other catchphrase
- “Aurora Borealis? At this time of year, at this time of day, in this part of the country, localized ENTIRELY within your kitchen..?"”
- ―Superintendent Chalmers
Chalmers originally hails from Utica, New York, but has also mentioned 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 matters such as his state of origin being New York (which is understood for being a primarily liberal state) and some of the decisions he has made in his job, specifically when he fired Ned for introducing prayer to school, however, this has yet to be confirmed. In the episode "How The Test Was Won", Seymour Skinner mentions that Chalmers has a daughter who he buys wrapping paper from. 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' absolute non-disciplinarian 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 the doors to the rooms open and bellowing "SKINNERRRRR!!!" or "SEYMOUR!!!", to which Seymour stammers, "S-Superintendent Chalmers!" His catchphrase has caused some paranoia in Skinner. Also, he has seven principals otherwise than Skinner, but he has never yelled their names, not even once. 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). Similarly, he had at least some grudging respect for Skinner, as he personally organized the surprise 20th-anniversary celebration of Skinner's time as principal of Springfield Elementary and even made an unscheduled and secret visit to the school specifically to make the announcement before Skinner arrived at the Teacher's Lounge (although he did express annoyance at Skinner's meticulous inspections throughout the school due to being forced to duck behind a corner and hide every time Skinner did an inspection before passing by the teacher's lounge, notably saying in response to the constant inspections "Good lord! The rod up that man's butt must have a rod up its butt." after barely arriving at the Teacher's Lounge undetected by Skinner). He also worked with Skinner during the disastrous Edutainment event at Springfield Elementary School, where he and Skinner portrayed Bud Abbot and Lou Costello's respective roles in their famous "Who's on First" comedy routine (although Chalmers eventually snapped at Skinner and walked offstage swinging his bat while bitterly referring to him as a "sexless freak" under his breath after the latter unintentionally spoiled the routine in the first six seconds by explicitly stating the wordplay of the pronoun and the actual subject, a person with that surname.).
Chalmers' 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 at that time was that 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' 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!" On a related note, he was also in on Skinner's attempt at cheating out grant money after it became apparent Lisa cheated on her test, with his scolding Skinner solely because the latter did not actually tell him the scoreboard came in and not because of the more unethical practice of using unearned grants when Lisa reported Skinner to him. 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 the suffixes, -er or -son, he would raise his tone, he once said "Stupid fish! Don't you want to be my DINNERRRRRR?!"
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 strongly implied that he is a widower.
In "Homer Goes to Prep School" it is shown that he is 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 eyebrows on their faces). Near the end of the episode when Lloyd mentions that in the new world he would be a big shot, Chalmers mentioned that he and the others were planning to seal him in a cave. When Lloyd mentioned he was going to poison their drinking water, Chalmers proclaimed that he will drink his own urine.
In the episode "Future-Drama", which takes place in the future, the Superintendent is practically a vegetable (because of a stim attack, which was revealed by Skinner), only capable of saying his trademark line while spinning around in a continuously 360-degree circle.
In a Simpsons Comic, he states that he went to LSU.
The Simpsons Game
Chalmers appears in The Simpsons Game walking around the Towns Square with Lenny Leonard, Krusty the Clown, Charlie (snpp) Julius Hibbert and Kent Brockman. Later when the Aliens arrive in Springfield, Chalmers tells Edna Krabappel the end may be upon them. Edna agrees and says they should roll around in the hay before they pass on. Chalmers refuses Edna then says "If Seymour ever found out he would be devastated." Chalmers then agreed to roll around in the hay with Edna.
In the second segment of "Treehouse of Horror XVII", Chalmers asks Skinner to just let the Golem kill him.
In the final segment of "Treehouse of Horror XX", Chalmers is one of the many residents who were turned into zombies.
In the opening of "Treehouse of Horror XXVIII", Chalmers is a candy bar called Chalmond Joy.
In "Shanksgiving", it is revealed he has a long lost twin brother named Police Superintendent Chalmers.
Behind the Laughter
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.
- It was revealed in 22 Short Films About Springfield that he is from Utica in New York.
- 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.
- He is right-handed.
- On several occasions, he and Agnes Skinner have tried dating, much to Skinner's discontent. It is not announced in the show itself but is hinted at.
- In the Latin American dub, his last name is Archundia in the first seasons.
- In "Daddicus Finch", Chalmers is seen attending Shauna's Bat Mitzvah at a synagogue as she recites the Scriptures in Hebrew, indicating that he may have Jewish heritage. However, he is frequently seen at the First Church of Springfield.
- In the Family Guy episode Shanksgiving, it's revealed that Gary has a twin brother, Police Superintendent Chalmers.
- 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
- You Don't Have to Live Like a Referee
- Homer and Lisa Exchange Cross Words
- The Debarted
- The Principal and the Pauper
- Marge Simpson in: "Screaming Yellow Honkers"
- 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?