David Hyde Pierce was cast as Sideshow Bob's brother, causing Pierce to joke, "Normally, I would not do something like this. But how often do you get a chance to work with an actor like Kelsey Grammer and, more importantly, play his brother?"
Kelsey Grammer's favorite Sideshow Bob line is "Lisa, you don't spend ten years as a homicidal maniac without learning a few things about dynamite."
The original script was run by the Frasier (1993) producers to make sure they were okay with it, and they only had one problem. There was a very brief scene in which Cecil talks to a visible character and refers to her as "Maris", who in Frasier is an unseen character, and the producers of Frasier said the scene should go.
The episode contains several references to Frasier (1993), with the intention of making it obvious that it was parodying the series:
- The mention of Arthur Fiedler's wake is an apparent reference and parody of Frasier Crane's upper class Seattle lifestyle.
- When Bart covers Cecil's eyes and asks "Guess who?", Cecil guesses "Maris". Maris was Niles' unseen wife.
- In an ad for the episode, Sideshow Bob while slamming his fist on the table angrily tells Cecil "Mother had high hopes of us becoming prominent psychologists, you know!", a reference to how Frasier and Niles were both psychiatrists.
- The title card just before the start of the second act says "Frasier is a hit show on the NBC television network" in a similar typeface and style as Frasier's intertitles, with jazz music playing over it as it does in the series.
The "Krusty the Clown Prison Special" is based on Johnny Cash's 1968 appearance at Folsom Prison. Krusty's song is a parody of "Folsom Prison Blues". Krusty's song mentions Tahoe, while the original mentioned Reno. (Both are in Nevada.)