Production
The first draft of "Day of the Jackanapes" was written by current showrunner Al Jean. In the DVD commentary for the episode, Jean said that he had always wanted to write an episode about Sideshow Bob, and that "Day of the Jackanapes" would be a good way to have the character return. He also said that the writers wanted to work with Kelsey Grammer, who portrays Sideshow Bob, again. "Of all the guest stars we've had who've been great, he's right up there as the very best", he said. Still, the writers had trouble with coming up with a story for Sideshow Bob since they had already explored several aspects of the character before. "It's just that we've done so many angles of whether he's, he's good, he's reformed and then his brother came to town..." executive producer and former showrunner Mike Scully said about the difficulty of writing episodes about Sideshow Bob.
At the beginning of the episode, Krusty is shown being pestered by network executives who comment on every choice he makes. He announces his departure from the Krusty the Klown Show after the executives give him notes during filming of a sketch. At the end of the episode, Mr Teeny is uncertain of where he should throw the plastic explosives that Bart wore. When he sees the two executives discussing in a room, he throws it onto them. Instead of dying of the explosion however, the pieces of the executives reconstitute into what Jean describes as a "super-executive". These sequences were inspired by Jean's dissatisfaction with some network executives, who he felt took control over a television series he was working on before he returned to The Simpsons in 1999. "I had just worked on a show on another network we had a show where there were a lot of notes from executives", Jean said of the inspiration for the scenes. The episode would originally have a different ending, but it was changed to its current iteration after the writers did not find the original ending humorous enough. When recording the DVD commentary however, Jean said that he was a bit dissatisfied with the new ending. "I think we did leave it a little hanging", he said.
During one of the recording sessions for the episode, The Simpsons' staff recorded "Hullaba Lula", a version of the 1946 song "Zip-a-Dee-Doo-Dah" with Grammer as Sideshow Bob on vocals. The song would originally be used in the episode, but the staff were not able to clear the rights for the song in time. It was therefore removed from the episode altogether, and remained unreleased until September 17, 2007, when it was included as a bonus track on the soundtrack album The Simpsons: Testify. Aside from Grammer, the episode also features American actor Gary Coleman as himself.
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