I’m really glad someone took the time to compile these clips of Superintendent Chalmers saying “Skinner!!!” on The Simpsons. I won’t go as far as former showrunner Bill Oakley, who has called Chalmers his favourite character (and wrote the “Skinner and the Superintendent” sequence that provided Chalmers’ greatest showcase), but I do love the guy, for two reasons:
1. Chalmers is, especially from season four (when he made his debut) through the Oakley/Weinstein years, basically a normal, rather dull person reacting to a crazy world. He appears to have some suspicion that this is not a normal universe, whereas even Lisa Simpson kind of accepts its rules at face value. The only thing stopping him from going crazy like Frank Grimes is that he hates his job, hates his life, and just doesn’t care enough to question what’s going on. Oakley and Weinstein loved what they called “humour of the boring,” plunking down dull reality into the middle of crazy cartoon comedy and seeing what comes of it. The whole George H.W. Bush was built around that, and so was the Frank Grimes episode. The real Seymour Skinner was also a regular boring guy whose humour was supposed to come from the presence of a regular boring guy in this universe. But Chalmers does it the best.
2. Like a lot of Simpsons supporting characters, he’s exactly halfway between making fun of a cliché and playing it straight. The Superintendent showing up to inspect the school, and the wacky things that ensue to get the principal in trouble with him – we had all seen that story before Chalmers showed up in “Whacking Day.” We had also seen the type of scene Skinner always plays with Chalmers, where he tries to make up an absurd lie or excuse to cover what’s going on. The Simpsons played these old ideas for all the very real comedy value they still had after all these years, while also twisting them a little or making them seem a little offbeat (mostly because Chalmers reacts to these situations not like a stereotypical superintendent, but sort of like a real person with real-world logic would). 30 Rock is the only show since the early Simpsons that has found that balance, managing to do very old-fashioned comedy and spoof it at the same time.