O’Brien had a glorious and prestigious run at “The Simpsons” that lasted from the show’s third season through its fifth. Many consider this time to be when the series really took off in quality. Given that “The Simpsons” is still running after 150 years, there was every reason for O’Brien to stay and continue writing for the series. When asked if he wished he had stayed, however, O’Brien answered with an emphatic “God, no.” The circumstances of the show’s writing were fraught to begin with. O’Brien said:
“When I was on ‘The Simpsons,’ imagine a room like this, only really crappy. On ‘The Simpsons,’ it was a room about this size [of a small garage]. Really rowdy furniture, all of us sitting around staring at each other from 9 o’clock in the morning until 9 o’clock at night, trying to think of ideas, and it was hard, hard work. I’m very hyperactive, so the writers used to use me to be their court jester. They would get bored and would say “Conan!” and I would get up and do all of this stuff and dance around, so as a writer I was always very energetic, and a performer.”
O’Brien served as the “court jester” for three years before being told, in a sort of code, that it was time for him to move on. O’Brien recalled a fellow writer, John Swartzwelder, saying to him that he was too talented to stay in the “Simpsons” writers’ room and that he needed to headline his own TV series. O’Brien took that not as a compliment, but a gentle encouragement to finally hit the road. He did.
His own shows, he notes, are far more active than any old garage-like comedy conference.
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