One of Oakley's challenges writing for The Simpsons was that there are few characters between the ages of 10 and 35.
Oakley edited the Harvard Lampoon while attending Harvard University.
Bill attended St. Albans School, a private college for boys in Washington, D.C.
Oakley is a big fan of Cartoon Network.
Bill and his writing partner Josh were the only executive producers and show runners of The Simpsons who did not write The Simpsons Movie.
Bill is a big fan of the animated movie, Fritz The Cat.
Bill and his writing partner Josh are close friends with Conan O'Brien.
Bill and writing partner, Josh Weinstein were hired onto The Simpsons writing staff after they wrote a spec Seinfeld script.
Bill along with Josh Weinstein wanted to carry on many traditions of The Simpsons that had been established when they ran the show, such as carrying on certain types of episodes.
Oakley has won three Emmy awards, in the field of "Outstanding Animated Series," for his work on The Simpsons.
Oakley has one son and one daughter. His son, James, can be heard in two of The Simpsons audio commentary tracks.
Oakley made an animated cameo in The Simpsons episode "The Itchy & Scratchy & Poochie Show" and in "Twenty-Two Short Films About Springfield."
Bill is married to The Simpsons and Mission Hill writer Rachel Pulido.
Oakley: (talking about Adult Swim) I love Futurama, and I'm thrilled that it's on there. It's another show that I think is perfect for Adult Swim. I have only seen a little bit of Sealab and Harvey Birdman, but both are very funny.
Oakley: The Simpsons has a big audience. Well, first of all, The Simpsons is now an institution, so it defies all traditional things. However, I think The Simpsons attracts -- or it used to -- every kid in the universe, some of their parents and then some grown-ups too. But if kids didn't watch it, the ratings wouldn't be very good. My suspicion is if adults who didn't have children were watching The Simpsons, their audience would be miniscule. And that's the audience we had for Mission Hill, I think.
Oakley: (talking about Mission Hill) I've let my daughter watch every episode except for the masturbation one.
Oakley: We actually have a top secret idea for a Simpsons film, but they have to ask us to do it first. But the Simpsons film may be a great mythological thing that is always talked about and never done. It requires a lot of time!
Oakley: (talking about Mission Hill) Well, it's all about satirizing parts of American culture. There's only about 30 percent that is goofing off and zany stuff. The whole construction of the show is about satirizing culture, from the characters to everything else.
Bill: (Talking about The Simpsons Spin Off Showcase episode.) Right off the bat we wanted to let people know they weren't watching a regular episode.