This episode featured then-89-year-old Bob Hope as a guest star, with his part recorded at his house by Jeff Martin and Conan O'Brien. He is however portrayed as his younger, Vietnam War-era self.
This episode has been used in England by the Anglican Church to give kids lessons in self-esteem, as well as pointing out Homer's sale of the Duff Beer ticket, marking a sacrifice on his part as Lisa's self-worth was more value to him than his pleasure.
Laramie's mascot Menthol Moose is a parody of Joe Camel, the mascot for Camel Cigarettes. At the time this episode was made, the company was accused of using the mascot to subtly market cigarettes to children.
According to Jeff Martin , "I'm not sure if we could do this episode today. People had a more innocent view of child beauty pageants before JonBenét Ramsey.
Lisa's swearing in as Little Miss Springfield is identical to Lyndon B. Johnson taking the Oath of office on November 22, 1963 the day Kennedy was assissinated. If you look closely, Marge is portraying Jacqueline Kennedy as she stands next to Lisa dressed all in pink.