There were difficulties getting this episode up to the minimum length of an episode and many scenes were added in post-production. The episode starts with a repeat of a couch gag that was first used in Lisa's First Word (1992), which is considerably longer than the typical couch gag. The crew added an Itchy & Scratchy cartoon and a few misleads as to who was trying to kill Bart. Even with all of these additions, the episode still ran short of time. This led to the creation of the rake sequence, which became a memorable moment of the episode, and the entire series.
Kelsey Grammer did not know that the rake scene was extended, because he had only done the moan once and was surprised when he saw the final product.
The show's writers admire Kelsey Grammer's singing voice, and try to include a song for each appearance including this episode. Alf Clausen commented that "[Grammer] 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."
Bart asks Sideshow Bob to sing the entire score of The H.M.S. Pinafore, which is then performed by Bob (Kelsey Grammer). In season 3 episode 4 ("Leapin' Lizards") of Grammer's sitcom Frasier, he sings part of the same segment of this score that he did in this episode of the The Simpsons.