Legendary ‘Simpsons’ Writer Bill Oakley on His Three Favorite Citizens of Springfield

While you might recognize him as “The Gordon Ramsay of Fast Food” or the founder of The Steamed Hams Society and Food Discovery Club, Bill Oakley is best known as a writer on The Simpsons from 1992 to 1998, or most of the show’s “Golden Era.” He and his writing partner Josh Weinstein, were responsible for classic episodes such as “Lisa vs. Malibu Stacy,” “Sideshow Bob Roberts,” and most famously, “22 Short Films About Springfield,” aka “Steamed Hams.”

If you’re familiar with that viral Simpsons sensation, you can probably guess at least a couple of Oakley’s favorite citizens of Springfield. But if not, here are a trio of his three most beloved non-Simpson Simpsons characters and why…

3 Mr. Burns

Mr. Burns is an old-timey guy, and we love to write old-timey stuff. I have a book here, The Thesaurus of American Slang, which is where Mr. Burns and Grampa Simpson’s old-time-isms came from during that era of The Simpsons.

2 Principal Skinner

Skinner is like so many teachers that Josh Weinstein and I had in our school. The 100th episode of The Simpsons, which is the one where Skinner gets fired and befriends Bart, has so many things that were taken wholesale from the teachers in our school. Like him conducting music to his reel-to-reel tape recorder, him having Diet Caffeine-Free Dr. Pepper and him standing there watching the washing machine.

We loved the details of his whole existence. We liked him as a character, and we liked him and Chalmers as a team.

1 Superintendent Chalmers

My most favorite character is Superintendent Chalmers. I actually have a painting of Superintendent Chalmers, and it’s the only Simpsons action figure that I have. I love that he’s the only sane man in town.

Green Acres was my favorite show as a kid, and 10 of the 12 people in the original writing staff of The Simpsons said that Green Acres was their favorite show, including Matt Groening. That’s a show about the only sane man in town, and Chalmers is the only sane man in Springfield. But he’s found a way to cope: He’s made a deal with Springfield that’s basically, “You never push too hard.” Skinner is obviously lying to him on a regular basis. Chalmers will ask a question, and Skinner will lie. Then he asks a second question, Skinner lies again, and Chalmers drops it. That’s how he survives in Springfield; he doesn’t push too hard.

That’s why I wrote “Steamed Hams.” The genesis was, “What if, this time, he didn’t drop it?” He kept asking questions that boxed Seymour into a corner more and more. He does drop it eventually, though. After 14 questions, he lets it go. The difference between Chalmers and Frank Grimes is that Frank Grimes couldn’t drop it, and that’s how he died. Chalmers doesn’t care enough, which is how he survives.