Bill Oakley and Josh Weinstein (Seasons 7-8)
You may also remember them from: Futurama, Mission Hill, The Cleveland Show, Portlandia, Gravity Falls
Bill Oakley and Josh Weinstein have been making comedy together since they were in the eighth grade. The pair founded a humor magazine in high school and grew accustomed to making people laugh together from then on. Unfortunately, all that experience as a team didn’t help them find much success early in their careers. Each of them struggled to find work for several years, until eventually, a Seinfeld spec script caught the eye of Al Jean and Mike Reiss, who brought the pair onto the show’s writing staff in Season 3. The two men would go on to pen some of The Simpsons’ most iconic episodes as staff writers, including “Bart vs. Australia” and the “Who Shot Mr. Burns?” two-parter.
But it was not until The Simpsons’ seventh season that the pair became showrunners. In that role, they intended to pull back from David Mirkin’s wilder efforts and focus more on the family. While Mirkin, Jean, and Reiss had all expanded the world of The Simpsons and devoted many memorable episodes to side characters and guest stars who became just as vital to Springfield as The Simpsons themselves, Oakley and Weinstein wanted to turn that attention back to Homer, Marge, Bart, Lisa, and Maggie. They aimed to tell more character-focused stories, founded on the relationships between the show’s central figures.
The two also oversaw some of the series’s most experimental episodes. Oakley and Weinstein idolized The Simpsons’ third season and aimed to emulate that era’s tone and sensibility. But they also carved out the time and space in the writers’ room to try different sorts of episodes that went beyond even Mirkin’s experimentation.
Sometimes, that innovation came in the guise of format-bending installments like “22 Short Films About Springfield”, an episode with tons of hilarious, semi-connected vignettes that gave each character their two minutes in the spotlight. Sometimes, it came in the form of a high-concept premise, like “Homer’s Enemy”, a dark but audacious episode where the show examined the Kafkaesque horror of what it would be like for a real person to experience Springfield and its most dimwitted yet improbably successful resident. Sometimes, it led to self-referential episodes like “The Itchy & Scratchy & Poochie Show”, which laid bare the issues of network pressures and the show’s advancing age in comic tones for all the world to see.
At the time, Oakley and Weinstein believed that the show was winding down, not realizing it was merely rounding out its first 10 years of what will be a minimum 30-season run. That assumption meant they were willing to try new ideas that broke the mold for typical Simpsons episodes and tested the limits of the format. But it also meant that they wanted to do justice to the family and to the series that they’d admired before they were ever a part of it. Their reign may have offered exaggerated events like Homer working for a Silicon Valley-tinged Bond villain or experiencing hallucinations brought on by Guatemalan insanity peppers, but it also addressed social issues like vegetarianism, immigration, and homosexuality, while taking time out to give Homer an emotional reunion with his mother and having Bart cheer on his sister in the biggest challenge of her life.
While occasionally the cracks in the foundation would show during this period, it was the era of The Simpsons where the different sensibilities of the prior six-year run were distilled into one incredibly diverse but cohesive whole. Oakley and Weinstein combined the down-to-earth bent of the show’s early years, the family-focused comedy and emotion that gave the show ballast thereafter, and the ballsy, absurd humor of their immediate predecessor. The result was two seasons that wonderfully represent all the different shades of The Simpsons.