Sideshow Bob Roberts
[1] Kelsey Grammer returns in his fourth major appearance as Sideshow Bob, who, in this episode, wins the Springfield mayoral election through electoral fraud to get revenge on Bart.
The episode received a favorable reception in the media, including a positive mention in I Can't Believe It's a Bigger and Better Updated Unofficial Simpsons Guide and Green Bay Press-Gazette.
Oakley and Weinstein drew inspiration for the episode from the Watergate scandal, and included many cultural references to political films and real-life events, among them All the President's Men and the 1960 United States presidential debates between Richard Nixon and John F. Kennedy.
Sideshow Bob calls local right-wing talk show host Birch Barlow and complains about being unfairly imprisoned for attempted murder.
However, after Quimby falls ill after a meet-and-greet with senior citizens and takes 'extra drowsy' cold and flu medicine, he loses a mayoral debate (hosted by Barlow).
Abusing his office, Bob proceeds to make the Simpsons' lives miserable, demoting Bart to kindergarten and threatening to demolish their house to build a new expressway.
While he initially denies the charges, Bart and Lisa bait his ego by claiming that he isn't intelligent enough to have rigged an election and was merely Barlow's accomplice, causing an indignant Bob to angrily take full credit for the fraud and hand over evidence to prove it.
[3] Sideshow Bob's campaign advert was based on the famous Willie Horton and "Revolving Door" political advertisements used by George H. W. Bush during the 1988 United States presidential election.
[3] The episode features several references to the film All the President's Men, which chronicled Bob Woodward and Carl Bernstein's investigation of Watergate.
[4] Barlow mentions Colonel Oliver North, Officer Stacey Koon and advertising mascot Joe Camel as being "intelligent conservative[s], railroaded by our liberal justice system".
"[1][2] Some of the deceased voters are Buddy Holly, Ritchie Valens and Jiles Richardson Jr. (The Big Bopper), who all died in a plane crash on February 3, 1959.
The episode also portrays Republicans as willing to break the law in order to achieve this; in this case, Bob commits electoral fraud.
This is most displayed in Bob's line: "Your guilty conscience may force you to vote Democratic, but deep down inside you secretly long for a cold-hearted Republican to lower taxes, brutalize criminals, and rule you like a king.
[9] Erik Adams writes that the episode "saves its greatest reserves of comedic contempt for a single entity—but it’s an entity that represents multitudes.
The subjects of the episode’s most effective political takedowns aren’t Republicans (though their local headquarters is portrayed as a dreamhouse from the Universal backlot circa Frankenstein) or Democrats (this in spite the fact that Springfield’s resident 'Spendocrat' dynamo, Mayor 'Diamond' Joe Quimby, willingly admits to all questions of his character save for illiteracy—and even that’s a recent development).
[11] Warren Martyn and Adrian Wood, in I Can't Believe It's a Bigger and Better Updated Unofficial Simpsons Guide, noted the episode was: "A stunningly outspoken political satire that drew considerable disapproval from the Republican Party when it was aired.
"[4] Eric Reinagel, Brian Moritz, and John Hill of the Press & Sun-Bulletin named "Sideshow Bob Roberts" as the seventh best episode of the series.
[17][18][19] In "Sideshow Bob Roberts", the word is used by the librarian who provides Lisa with the town's voting records, in response to her questioning their unclassified nature.
In an editorial for The Washington Post, Bill Oakley commented, "It’s hard to believe that the Sideshow Bob defense of Trump will be long-lived, as it fails to stand up to even the slightest scrutiny.
