It certainly isn’t “unpossible” to uncover a new reference or new meaning in a classic episode of The Simpsons, even one as pored over as “22 Short Films About Springfield.” But as former Simpsons writers and executive producers Bill Oakley and Josh Weinstein tell The A.V. Club ahead of that episode’s 25th anniversary, there’s at least one question they’d never been asked about “22 Short Films.”
“22 Short Films” was born of the efforts to beef up season four’s “The Front,” which came up a minute short of the minimum runtime. Not only did “The Adventures Of Ned Flanders” help “The Front” hit the 22-minute mark, it proved there was potential and interest in the lives of non-Simpsons Springfieldians. As Oakley told MEL Magazine’s Brian VanHooker in 2020, he and Weinstein had “always wanted to do more of those” one-offs, “but every one of our episodes was so bloated that we never had the chance.”
In season seven, the decision was made to “do a whole episode of nothing but those things,” and the result was “22 Short Films About Springfield,” an intricately woven but still zippy installment of the show. 12 writers worked on the episode, including Oakley, Weinstein, series creator Matt Groening, and Greg Daniels (the last of whom also supervised the script). Bart and Milhouse pause mid-shenanigans to muse on the lives of all the other people in their hometown, and “22 Short Films” flits about from there, dropping in on everything from the latest antiquated jargon-laden diatribe from Mr. Burns to another bit of quackery by Dr. Nick Riviera. Like many of the show’s best episodes, “22 Short Films” is as dense with jokes as it is pop culture references, including nods to E.R. and Pulp Fiction. Even its title is a play on the then-recent arthouse sensation Thirty Two Short Films About Glenn Gould—a biopic whose subject would inspire a classic Simpsons one-liner a few seasons later.
“22 Short Films About Springfield” was well received by viewers and critics when it first aired on April 14, 1996. But it gained a whole new head of steam five years ago, as “Chalmers Vs. Skinner,” Oakley’s contribution to the script, birthed a ton of memes (leading to its current online sobriquet, “Steamed Hams”) and some old-fashioned crank calling, er, commenting. The standout segment, in which Principal Seymour Skinner (Harry Shearer) hosts an “unforgettable luncheon” for Superintendent Gary Chalmers (Hank Azaria), has been remixed countless times and given the oral history treatment.
Oakley and Weinstein, who also served as showrunners during season seven, have had plenty of opportunities to discuss “Steamed Hams” and the rest of the “22 Short Films About Springfield” in the years since. It wasn’t that long ago that Oakley shared his original draft for “Steamed Hams,” and the world realized how close we’d come to watching a series of unfortunate, ham-related events unfold over the course of a dinner instead of a lunch. A few changes were made to Oakley’s script, including the addition of Chalmers’ opening line: “Well Seymour, I made it, despite your directions.” It’s a great bit, in part because, like so many of the “22 Short Films,” it communicates so much about the characters in the segment so efficiently. Skinner and Chalmers have always had an uneasy dynamic; the superintendent has said he’s “really bugged” by the principal. So even if Skinner had somehow managed to provide proper directions, Chalmers would have found them lacking anyway.
At least, that’s what we always thought when watching “22 Short Films About Springfield” in years past. But upon a recent rewatch of season seven, we were reminded that Chalmers had been to the Skinner home on at least one other occasion. In “Bart The Fink,” the 15th episode of season seven, Chalmers walks Agnes Skinner to her front door after a night out. When Seymour appears on the porch in his nightshirt and cap, he draws the ire of his mom and his boss. Luckily, a forlorn Krusty The Clown flies by in his plane, the I’m-On-A-Rolla-Gay, thereby defusing this awkward moment at the Skinner home.
And thus we found ourselves with yet another detail in “22 Short Films” to obsess about. If Chalmers had been to the Skinners’ before, why did he need directions? Why doesn’t he recognize Agnes’ voice when she screams “Seymour, the house is on fire!” Did everyone just agree to pretend it had never happened? Even while considering all the other ways that The Simpsons has ignored, tinkered with, or eschewed continuity, our curiosity was piqued. So we reached out to Oakley and Weinstein for comment. (We also contacted representatives for Greg Daniels, but were unable to get in touch by the time of publication.)
In an emailed response, Oakley tells The A.V. Club “that fact literally never occurred to me until I read this email,” which briefly made us wonder if we were being too nitpicky. But as it turns out, “that line indicating that Chalmers had never been there was not in my draft.” It seems “it was added by Greg Daniels who did the conforming of all the segments and put them in order (which is why it is a lunch in the episode but a dinner in my draft).” The fact that Gary and Agnes had been on a date a few episodes prior “likely did not occur to” Daniels, though Oakley writes “While we were concerned about some continuity, I think we would have ignored that here to make the joke work.”
Taking a break from working on new episodes of Disenchantment, Weinstein says he and Oakley have always welcomed the chance to talk about The Simpsons—even 25 years later, when the topic of conversation is why Agnes Skinner and Superintendent Chalmers’ brief romance in “Bart The Fink” is seemingly ignored in “22 Short Films.” Like Oakley, he feels it was a mere oversight, and that while a pact between Agnes, Seymour, and Gary to never speak of it again “would be a better explanation, the truth is, we just didn’t remember. And obviously, ‘despite your directions’ is such a great line, we just loved it when somebody pitched it and it went in, and that was it.”
Weinstein and Oakley loved writing episodes with Chalmers and Skinner, and not just because they took inspiration from their Washington, D.C. prep school teachers for the latter. “We just loved that relationship,” Weinstein says. “‘Sweet Seymour Skinner’s Badasssss Song’” was one of “Bill’s favorite episodes so he chose to write about Skinner and Chalmers for ‘22 Short Films.’” Weinstein has enjoyed seeing how Chalmers and Skinner’s relationship has evolved over the years (they’re producing partners, like Weinstein and Oakley once were) but notes that things between them are “still quite touchy.”
The abiding appreciation for “22 Short Films About Springfield” kept the hope of a spin-off based around the show’s supporting cast alive for years. “That spin-off was going to be called Springfield, and Bill, me, and Matt Groening were really into the idea,” Weinstein says. “At the time, I think Jim Brooks wasn’t crazy about the idea, so it was kind of shelved.” Asked if they’d come up with an opening credits sequence for Springfield to match the memorable one from the original series, Weinstein says they didn’t make it that far. “We kind of just fleshed it out roughly, where we knew that each episode would either be one story or maybe two stories about the side characters of Springfield. It wouldn’t involve the Simpsons, but they might make a cameo.”
There were no plans to add any new Springfieldians, according to Weinstein. When asked which extant characters he’d been most excited to write about, Weinstein says “It would be the real side characters, like Disco Stu or the Sea Captain, that seem like they’re sort of one-joke characters, but obviously they have some sort of life. That would have been really fun to do. But then also people like Chief Wiggum and his family, with Ralph. To be able to do a whole episode about them would be delightful.” Season eight’s “The Simpsons Spin-Off Showcase” wasn’t intended as a consolation prize for the never-launched spin-off, because according to Weinstein, that episode is “a parody of crummy spin-offs that we had all witnessed watching TV in the ’70s and ’80s, which is the particular era of crummy spin-offs.”
And as far as getting too granular with questions about The Simpsons, Weinstein says there’s no such thing: “It’s highly entertaining. I love when people find these things and it’s like, ‘Oh my God, we didn’t think of it at the time, and it’s been 25 years and no one’s pointed that out.’ Kudos to you for that.”