Mike Scully, the writer of the episode, based it on an experience in his childhood. Scully was twelve years old when he paid a visit to the Bradlees discount department store in West Springfield, Massachusetts. A "bunch of guys" were shoplifting at the store and they "pressured" Scully into shoplifting as well. He ended up getting caught outside, and "had one of the most traumatic moments" of his life. "To this day it still terrifies me", Scully said. He jokingly told Variety, "It's great to be paid for reliving the horrors of your life."
Josh Weinstein called Lawrence Tierney's appearance "the craziest guest star experience we ever had". In addition to yelling at and intimidating employees of the show, Tierney made unreasonable requests, such as abandoning his distinctive voice to do the part in a southern accent and refusing to perform lines if he did not "get the jokes". Despite this, Weinstein and Bill Oakley thought Tierney did a good job. Weinstein said, "He certainly delivered and he's one of my favorite characters we have had [on the show]."
This was the first Christmas episode the producers had done since the first episode of the series, Simpsons Roasting on an Open Fire (1989). Bill Oakley said that nobody in the writing staff wanted to "try on Christmas" because it was "so famous" as being the first episode.
Video games seen in the case alongside Bonestorm are Save Hitler's Brain, Swim Meet, Canasta Master, Operation: Rescue, A Streetcar Named Death, and Sim Reich.
The title comes from the poem "Death Be Not Proud" by John Donne, also known as Holy Sonnet X. "Death be not proud, though some have called thee Mighty and dreadful, for, thou art not so."