The episode contains the first use of the word "meh" in the show. The word, which was later included in the Collins English Dictionary, is credited as being popularized by the show, principally following its usage in the season twelve episode Hungry Hungry Homer (2001). Here, the word is used by the librarian who provides Lisa with the town's voting records, in response to her questioning their unclassified nature.
Sideshow Bob runs for mayor on the Republican ticket. Kelsey Grammer is a noted Republican who has voiced political aspirations including US President and NYC mayor.
Sideshow Bob was released by Democratic mayor Joe Quimby after pressure from Republican-inspired protests. In Black Widower (1992) he claimed he and his prison mates would be released on the streets once the Democrats were back in power.
The episode does not feature a chalkboard or couch gag, cutting straight from the clouds to the TV. The 1994 original airing and some syndication edits have included a couch gag.
Much of the episode is based on the Watergate scandal, as well as other real-life political events. The two Republicans who follow Bob around were based on H. R. Haldeman and John Ehrlichman, two of Richard Nixon's closest advisors during Watergate. Sideshow Bob's campaign advert was based on the famous Willie Horton and Revolving Door political advertisements used by George Bush during the 1988 United States presidential election. Birch Barlow's question to Mayor Quimby about whether his stance on crime would differ if it was his family being attacked is a reference to Bernard Shaw's similar question to Democratic candidate Michael Dukakis during the 1988 presidential debates. Quimby's appearance during the debate parodies Richard Nixon's appearance during his first televised debate with John F. Kennedy during the 1960 presidential election. Nixon had recently recovered from a cold, and sweated considerably throughout, something that was detrimental to the impression he made in the debate.