Bill Oakley was a writer at The Simpsons from seasons 4-6 and an executive producer/showrunner with his writing partner Josh Weinstein from seasons 7-8. I talked to him at length about his experiences in that famous writer's room. This is a transcription of part of that conversation, edited for length and clarity.
Twice a year, from at least season three 'til season eight, there'd be these story retreats where everybody would come and present their ideas for episodes. We'd get a big conference room in a hotel about a hundred yards from the office, and we'd go around and everybody would tell their ideas, one by one. It was sort of like opening Christmas presents on Christmas morning; we’d go around in a circle and everybody would have a turn or two.
It was always a huge treat to see. You had no idea what George Meyer (for instance) was going to say, and suddenly it was like this fantastic Simpsons episode pouring out of his mouth that you never dreamed of. And it was like, wow, this is where this stuff comes from.
A lot of times people worked collaboratively, too. We would work with Conan, back and forth, and we'd exchange ideas and help polish them up. And so everybody would usually come with two, sometimes three ideas. You'd take fifteen minutes and you'd say your idea in front of everybody — all the writers, Jim Brooks, Matt Groening, Sam Simon when he was still there, and also the writers assistants who would be there taking notes on all this stuff.
Many people were very, very intimidated by all this stuff and it was like the worst part of their year. But for us, it was our favorite part of the year. My writing partner Josh Weinstein and I would work really hard on these things and we'd usually have a couple of ideas stored up that we'd been working on for a couple months, and we just liked the opportunity to discuss them and have everybody there pitching in their jokes. And, you know, usually you would get laughs. And people would give suggestions like, oh, this could happen or that could happen, and you'd usually talk about the idea for about twenty minutes, with everybody pitching in stuff off the top of their head.
You wanted to have a story that had a beginning, middle, and end. You didn't necessarily have to have the act breaks, but you couldn't go into the retreats with just one sentence, you know, something like "Bart vs. Australia." These are busy, highly-paid people, and you didn't want to waste Jim Brooks' time with something half-assed. I'm pretty sure there was at least one guy who got canned after his crummy performance at the story retreat. So you wanted to be prepared, as your job was on the line to some extent. So you wanted to come in with a story that would take ten minutes to tell and would have the act breaks, or at least some semblance of the act breaks.
So the writers assistants would take all those notes, and they'd basically go into storage until it was time to do that episode. And then for that episode we'd be in the writer's room which is, like, ten or twelve guys, and we'd have a "pitch out" lead sometimes by the show runner but usually, often, lead by the writer. We'd just go through scene by scene, go through the broad strokes, fix any story problems, and just spend the day kind of micromanaging the episode and trying to sort of break it down into scenes as much as you could. Sometimes it could only take an hour and other times it would take two or three days. And when we were done, the writer would go off and write an outline.
And the outline used to be way, way, way long. Like, it would be almost an hour of television. The outlines would always be about forty single-spaced pages, and the show runner would read it and give his thoughts and suggest some cuts and whatnot. And then you'd have two more weeks to write the script. And as soon as you started converting that outline into a script, we'd always realize that the script would be twice as long as it's supposed to be. So a lot of stuff would be cut — cut, cut, cut — and then you'd turn in the script.
The most you could get away with was like a 62 page script. At the table readings the scripts had to be like 47, and by broadcast it was usually 42, so the most your first draft could be was 62 pages without getting in trouble. So every draft we'd turn in was usually 62 pages. But then, when you turn in the first draft, it would go to the rewrite room and usually spend anywhere from a few hours to a few weeks, going through the script line by line, under the direction of the show runner, rewriting it to perfection, table-read level. Then after the table-read there's usually a rewrite over a day or two, and then they record, and then the track goes off to the animators at that point. That’s the structure we used for the entire time I was there, from season three to season nine.
Also be sure to check out the second part of this piece, The Lost Jokes and Story Arcs of "Sweet Seymour Skinner's Baadasssss Song," in which Bill walks through the writing process and lost jokes of one specific episode from season five.
Bill Oakley can be found on Twitter at @thatbilloakley.