"Sideshow Bob's Last Gleaming" was the first episode of "The Simpsons" to be directed by Dominic Polcino. Polcino had worked as an assistant director on the show and had left the show, but was offered a chance to be a director. He describes the episode as a "tough one to start with", especially the scenes with the Wright Flyer. An early version of the script featured a longer scene at the air show that featured Hans Moleman flying an early flying machine. The scene where Milhouse is in a jet pretending to fire missiles at his parents because he's upset with them, would later inspire the episode "A Milhouse Divided". In that episode, Milhouse's parents become divorced, and it is also a reference to Dr. Frasier Crane.