Josh Weinstein said that this episode was an opportunity for him, Bill Oakley, and John Swartzwelder to "go nuts" with the "Burns-ism". He said that they enjoy writing for characters such as Burns and Abe Simpson because of their "out-datedness", and because they get to use thesauruses for looking up "old time slang". For example, Burns answers the phone by saying "Ahoy, hoy!", which was suggested by Alexander Graham Bell to be used as the proper telephone answer when the telephone was first invented.
The number for Moe's Tavern is 76484377 (S-M-I-T-H-E-R-S).
When Bill Oakley and Josh Weinstein took over as showrunners, they wanted to "take the show back" to the Simpson family. Their goal was to have at least 15 episodes per season that revolved around the family or a member of the family, but they still wanted to do the annual Halloween episode, a Sideshow Bob episode, an Itchy and Scratchy episode, and a "format bending" episode, which in this season was 22 Short Films About Springfield (1996). They wanted the family episodes to be realistic, and Oakley thought this was a good example.
Bill Oakley commented that the stuffed polar bear had always been in Burns' office, and they were excited to "finally" have a use for it.
The episode was written by John Swartzwelder, who got the story from another member of the writing staff, Mike Scully. When Scully pitched the idea to the writers, Bill Oakley was surprised that it had not been done earlier on the show. He thought the story sounded like something that would have been done by the third season because it was "simple" and "organic".