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One of Oakley's challenges writing for The Simpsons was that there are few characters between the ages of 10 and 35.
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Oakley edited the Harvard Lampoon while attending Harvard University.
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Bill attended St. Albans School, a private college for boys in Washington, D.C.
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Oakley is a big fan of Cartoon Network.
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Bill and his writing partner Josh were the only executive producers and show runners of The Simpsons who did not write The Simpsons Movie.
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Bill is a big fan of the animated movie, Fritz The Cat.
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Bill and his writing partner Josh are close friends with Conan O'Brien.
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Bill and writing partner, Josh Weinstein were hired onto The Simpsons writing staff after they wrote a spec Seinfeld script.
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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.
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Oakley has won three Emmy awards, in the field of "Outstanding Animated Series," for his work on The Simpsons.
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Oakley has one son and one daughter. His son, James, can be heard in two of The Simpsons audio commentary tracks.
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Oakley made an animated cameo in The Simpsons episode "The Itchy & Scratchy & Poochie Show" and in "Twenty-Two Short Films About Springfield."
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Bill is married to The Simpsons and Mission Hill writer Rachel Pulido.