_Bill Oakley is an Emmy Award-winning veteran American writer and producer, involved in many of television’s best loved shows. After attending Harvard University, Oakley and his writing partner Josh Weinstein wound up writing for America’s favourite family – The Simpsons.
There, the duo wrote some of the show’s most famous episodes, including the two-part special “Who Shot Mr. Burns?” Rising to the rank of “showrunner” – the TV industry term for a show’s overseer and main producer – Oakley and Weinstein presided over the show’s seventh and eighth years, which are widely considered to be its last classic seasons._
**Alex Gibson**: Can you tell us about your early life, where were you born, and what were some of your early influences?
**Bill Oakley**: I was born in Westminster, Maryland and grew up in Union Bridge, MD. I moved to DC when I was 10. My biggest early influence was MAD magazine. My brother went to college and left about 100 issues in the attic. I read them all over and over. Later, my influences were National Lampoon, SNL and especially SCTV, in high school. [And _Monty Python_] but it was hard to find back then, only on PBS late at night. I did see Holy Grail when I was little and I thought it was really scary! I did have every single MP record album though.
**Alex**: You’ve been writing comedy since high school, is that correct? With The Alban Antic?
**Oakley**: Yes, I was primarily a cartoonist in those days, but I started the Antic and Josh [Weinstein] was co-founder. We were brought together in the ninth grade by a shared love of comedy in what was a pretty stiff environment.
**Alex**: You also, like many people who later wrote for _The Simpsons_, went to Harvard and wrote for the Harvard Lampoon. What was that like and how do you think it helped shape _The Simpsons_?
**Oakley**: As I’m sure you know, no Lampoon people actually “created” _The Simpsons_. But in assembling the original staff Sam Simon did end up hiring several and I think it just built upon itself, in that Lampoon people from similar eras tend to have fairly similar comedic tastes. So that during Seasons 5-8, there was usually a very large percentage of Lampoon people (10 of 12 in our years, I think). The Harvard Lampoon magazine is very rarely good or funny but it provides the members/editors with a forum for non-stop practice and improvement of their comedy-writing skills so that by the time they graduate from college, it’s as if they have the experience and skills of someone who has been a pro for four years.
**Alex**: After Harvard, how did you get into writing? It seems like a fast progression for a lot of people; was that the case for you?
**Oakley**: It only seems fast because I usually leave out the unemployment parts! First I went home to DC and I got a job writing promos at “America’s Most Wanted” which was the only non-news network TV show in DC. Anyway, it was actually almost four years of small jobs on failed projects and a lot of unemployment until we finally got that big break where Mike & Al assigned us “Marge Gets a Job”.
**Alex**: And after that you ended up joining the staff full time, what was it like arriving on _The Simpsons_ as big fans of the show beforehand?
**Oakley**: It was incredible. And very intimidating. We were so ignorant of the whole process that we thought as “Story Editors” we would actually be editing stories written by the others. We were thrown into a room with 8 of the best comedy writers who ever lived and for those first few weeks I wrote down everything I said that actually got used. It was a very short list.
**Alex**: The two of you eventually took over running the show in Seasons 7 and 8. A lot of the episodes were what you have termed experiments and expanded the characters’ backstories. Was this something you were especially interested in, or did you even think the show would end soon, and so wanted to flesh out the mythology, as it were?
**Oakley**: We were NOT doing that because we thought the show would end soon, although I don’t think anybody at the time thought it would continue past another season or so. We came to the showrunning job with a specific plan: To do “classic”-style family episodes, plus one Itchy & Scratchy and one Sideshow Bob per year, plus at least one “format-bending” episode a la “22 Short Films About Springfield”. I think we did those backstory episodes because we were genuinely interested in what made those characters tick and wanted to flesh them out a bit, plus we did not want to repeat ourselves, so we had to start looking outside the family for some of the episodes.
**Alex**: “The Principal and the Pauper” [where it is revealed Principal Skinner is an imposter] proved to be probably the only negatively received episode of your era. Having listened to [writer] Ken Keeler’s explanation on the DVD, I understand the episode’s premise as an experiment in TV, and I never hated it anyway.
**Oakley**: Good, I think the commentary is pretty much the end-all be-all on that topic. […] I certainly never thought anybody would hate it. Again, it was drawn from a real-life story that Ken found and “Return of Martin Guerre”. I’m not sure clarity was the problem. I think it was pretty clear what happened. I think people reacted much more violently to the tampering-with-backstory thing than anyone expected they would.
**Alex**: _The Simpsons_ is a largely collaborative show, and an episode credited to you might actually contain little material pitched by you. Are there any jokes you wrote or pitched that have been well-received by fans?
**Oakley**: The most well-received thing I have ever written entirely by myself was “Skinner & the Superintendent” from 22 Short Films. I was just looking through the first draft and aside from some trims, what went on the air was what I turned in. Also in the broader sense, the 3D Halloween segment was my notion – although David Cohen wrote it – and it was my idea for Homer to have an enemy who was a stiff although it went through a lot of work by others before becoming Frank Grimes, […] but I cannot remember the specifics, I am more of a character comedy person than a gag man.
_After leaving The Simpsons, Oakley and Weinstein created the short-lived series Mission Hill and also worked on Futurama. Oakley now writes for the series Portlandia._