American actor Kelsey Grammer was brought in to guest star as Sideshow Bob for the third time. At that time, Grammer had become a household name as the lead of the television series "Frasier", which was in production at the same time as this episode. Grammer did not know the rake scene was extended because he had made the moan only once and was surprised when he saw the final product. The show's writers admire Grammer's singing voice and include a song for each appearance, including this episode. Alf Clausen, the primary composer for "The Simpsons", commented that " is so great. He's just amazing. You can tell he has this love of musical theater, and he has the vocal instrument to go with it, so I know whatever I write is going to be sung the way I've heard it."