Superintendent Chalmers’ Breakout Year on The Simpsons

The show’s de facto real-world representative appeared more often than ever in 1995-96, aka Season 7.

Wednesday’s silver anniversary of “22 Short Films About Springfield” was the most opportune occasion for Simpsons enthusiasts to reflect on the meme magnet that is Steamed Hams. The AV Club, Forbes, and The Hollywood Reporter were all over it this week, with some cultivating substantial input from the scene’s masterminds.

But other search results and their dates, such as August and December of last year or September of 2019, prove there is no bad time to reflect on the singled-out jewel from a Season 7 gem. (So there’s no need to pull a Homer and remind me the anniversary “was yesterday, moron.”)

Nor is there any wrong moment to break down the bit’s catalyst/straight man, Superintendent Gary Chalmers. Besides being the character’s most rehashed moment, and with good reason given the absurdity of Principal Seymour Skinner’s kitchen catastrophe cover-up, Steamed Hams is the capper on his most prolific season up to that time.

That upgrade in appearances was no accident. Chalmers is all but the real world’s recurring ambassador to Springfield, which makes him the favorite of mid-’90s Simpsons writer and showrunner Bill Oakley.

Oakley confirmed as much in a 2005 Q-and-A with himself and colleague Josh Weinstein on the Simpsons fan forum nohomers.net. “He is the one adult in Springfield who seems like he’s almost a normal, serious person,” he wrote, later adding, “thrown into the sea of kookiness that is Springfield, it’s funny to see him react.”

Indeed, one most likely does not envy Chalmers in his position. Nonetheless, he stands for an illusion of interaction between the viewer and the show, sustaining enough distance for endless good laughs in the living room.

Oakley reiterated his point this week in The Hollywood Reporter. There Oakley told author Ryan Parker that, despite the superintendent’s unique awareness of everyone’s constant flubbing and ludicrous dishonesty, “he just doesn’t care enough to pursue it.”

Aside from when we do our nerdy nitpicking, which is our answer to Chalmers’ trademark eruptions and disciplinary resorts, that assessment applies to the show’s fan base. To some extent, so does Oakley’s appreciation for the character and his designation.

Last year a Screen Rant subheadline called Chalmers “the show’s secret weapon.” The piece references Steam Hams, but focuses primarily on another eventual meme moment, the one where Ralph Wiggum greets “Super Nintendo Chalmers” in Season 10.

As columnist Padraig Cotter articulates, the way Ralph butchers the honorific — through a reference to a hot ’90s gaming system, no less — and the way Chalmers only reacts facially perpetuates the latter’s classic handling of incompetence. He generally refrains from finishing his questions, however warranted they may be, as Skinner’s explanations grow more preposterous.

Fittingly for those of us with an admitted bias for the ’90s, Chalmers first appeared shortly after The Simpsons hit his stride. He then peaked, at least in terms of frequency, along with the series itself mid-decade.

“This is one reason Chalmers is now recognized as one of the funniest side characters on The Simpsons and why he seems to keep appearing in its best memes,” Cotter concludes.

And fittingly for those of us with an admitted bias for the ’90s, Chalmers first appeared shortly after The Simpsons hit his stride. He then peaked, at least in terms of frequency, along with the series itself mid-decade.

Per Fandom’s Simpsons section, Chalmers has appeared in 60 episodes through the first 32 seasons. Although it neglects to mention “The PTA Disbands” from Season 6, where Chalmers ratchets his position in the cast with three appearances out of five episodes.

Counting that toward 61, his first 12 teleplays were within the show’s first eight years, including 10 spanning Seasons 6 through 8 (1994 to 1997). And with an unmatched four episodes alone, Season 7 nearly doubled the superintendent’s all-time log from five within the previous six.

The Steamed Hams segment in “22 Short Films About Springfield” punctuated that milestone. It also cemented the season that established him as a character good for much more than catching only the most unfortunate occurrences at Springfield Elementary.

Within the preceding seven months, Chalmers can vouch for Skinner’s awkward alibi in “Who Shot Mr. Burns? (Part Two)”; gives the principal a reason to dread him beyond school grounds (“Bart the Fink”); and asks his subordinate “Why are there children walking on my head?” during the “Down with homework” riot in “Team Homer.”

The latter scene marks a return to Chalmers’ founding purpose, namely ill-timed visits to Skinner’s jurisdiction. He had previously brooked a backside injury from a tractor Bart was joyriding through the playground (Season 4’s “Whacking Day”), fired Skinner when Bart’s disallowed dog wreaked havoc on the gym (Season 5’s “Sweet Seymour Skinner’s Baadasssss Song”), and found Bart passed out in the nurse’s office (Season 6’s “Round Springfield”).

Outside of Bart’s inopportune antics, and on the heels of his “Round Springfield” cameo, Chalmers obligatorily tears into Seymour for his handling of the teacher’s strike. Three episodes later, he spontaneously visits early in the sixth-season cliffhanger — “Who Shot Mr. Burns? (Part One) — to investigate an oil eruption. (He implicitly does not even need to hear which school endured the explosion. He puts the elements together and comes up with “Skinner!” in a one-man game of word association.)

Elsewhere in Season 7, the superintendent can be seen implicitly fostering a relationship with Skinner’s mother. The side gag builds up to the “Bart the Fink” plot’s continuation, as Krusty interrupts Seymour’s discomfiting discovery through his faked death by plane crash.

After Chalmers made a personal record four appearances and expanded his horizons beyond school grounds in Season 7, there was hardly any turning back.

But it is not a one-and-done narrative, as Chalmers and Agnes are occasionally seen together again after the ’90s. Perhaps that is why, in “Team Homer” five weeks prior to “Bart the Fink”, he is eager to see her dress turn tie-dye from the rain. (And be honest, didn’t you the viewer kind of want to see that yourself?)

That is the first foreshadow of his implicitly on-again, off-again fling with the elder Skinner. Although it makes one wonder why, in between, Chalmers does not express more overt concern in “22 Short Films About Springfield” when Agnes cries for help over the fast-spreading flames Seymour somehow passes off as aurora borealis.

Weinstein and Oakley more or less addressed this point when pressed by the AV Club’s Danette Chavez this week. The focus was Chalmers alluding to Seymour’s poor directions to the house, which the superintendent should not have logically needed. Oakley told Chavez “we just didn’t remember” the moment from “Bart the Fink” and besides, the line was too good to discard.

You could also say that Chalmers, like the rest of us from a normal universe, had other things to see in Springfield.

Regardless, the “despite your directions” line, in turn, represents the real world’s representative on the show. Skinner’s straight man had brought too much to only show up once a year, so there was hardly any turning back for his part as a supporting character.

The plot-setting theft of his prized H atop his Honda — for which Bart is presumed responsible, then unequivocally absolved — in “Lisa’s Date With Density” was just one of three shining moments to come in Season 8. That year also witnesses his fleeting chastising of Skinner (opposite Agnes) for patronizing a burlesque house and his crackdown on Seymour and Edna’s romance.

Then again, there are those who point to “The Principal and the Pauper” — an early ninth-season storyline that inevitably factors Chalmers in heavily — as the start of the program’s decline.

But at least before that, Chalmers sandwiches a pair of three-episode seasons around his career year of four in 1996-97, swelling his standing in The Simpsons’ chronicles concomitant with the show’s heights. And he even has an extra moment in the crowd, and presumably joining the viewers, at the end of “22 Short Films About Springfield”, joining the role-reversing laugh at Nelson Muntz (his soon-to-be H thief).