When Bart, Milhouse, Martin, and Nelson drive through Branson, they pass a marquee that reads "Lurleen Lumpkin and Pip Diddle Tonight." Lurleen Lumpkin was the woman Homer became a manger for when he discovered her in a bar in Colonel Homer (1992).
There was a debate over where the children would go, and Fort Lauderdale, Florida, was first suggested, but the writers eventually decided to have them go to a "funny unlikely place."
Josh Weinstein said that the writers were always looking for combinations of characters that had not been done many times on the show. Homer and Lisa had not been done "too often" and they wanted the two characters to bond and get closer to each other.
The boys also see an Andy Williams concert in Branson, Missouri, and the marquee advertising it outside reads "Wow, he's still got it - Look magazine", with Look having been out of business for 25 years when the episode first aired.
The episode was written by Richard Appel, who wanted to do an episode that had two things; a "go to work with your parents day" and Bart getting a driver's license. The "go to work with your parents day" idea appealed to Appel because it was something he "lost the right" to do when he went from public school to private school as a child. Appel considered those days to be his favorites because he "didn't have to do anything" at his parents' job. The idea of having a driver's license was something that Appel dreamed about when he was younger.