|Sideshow Bob Roberts||
- Joe Quimby proposes a new expressway at the Springfield Retirement Castle. The seniors want to call it the Matlock expressway after the television series Matlock, a favorite show among senior citizens.
- Sideshow Bob was released by Democratic mayor Joe Quimby after pressure from Republican-inspired protests. In "Black Widower" he claimed he and his prison mates would be released on the streets once the Democrats were back in power.
- Some prints of this episode cut the whole intro, as the text reveals the TV credits.
- Fox Broadcasting Company said that the episode was running too long to have the couch gag. Along with "Bart The General" And "Life on the Fast Lane," the episode Marks this one as the third episode to not have a couch gag or any gags.
- The Springfield Republican party members are:
- Rich Texan
- Birchibald T. Barlow
- Rainier Wolfcastle
- Blue Haired Lawyer
- Dr. Hibbert.
- Sideshow Bob's middle name "Underdunk" is mentioned for the first time.
- Names, which are on the voter records, are:
- Animals, which "voted" for Bob, are:
- The end of the episode, where the prison rowing team is going to compete against Princeton alumni, is the first time Bob is disparaging towards the school (the second is when he refers to it as "clown college" in Brother from Another Series).
- In the Mythbusters "The Simpsons Special" episode, Adam and Jamie tested a myth about this episode: A person hanging onto a wrecking ball can protect a house from damage if the ball swings to pin him against the wall? In order to test this myth, they built a real life Homer Simpson with rubber and filled with water to match Homer's weight (239 pounds). in the final test, Homer was intact, but the house was damaged. The myth was classified as "Plausible".
- This is the first time in the series were the catchphrase "Meh" is used, with a Librarian using it to answer Lisa's interjection about votes being secrets.
- Though never explicitly stated, the reason Smithers helps the kids to take down Sideshow Bob in secret by giving them information is likely due to the fact that Bob is affiliated with the Republican Party, who have a long tradition of being opposed to gay marriage; something that would not sit well with the closeted Smithers.
- Only names of dead people and animals appear on the voter records, but Bart's elephant Stampy, one of voters, is not dead or buried at the Springfield Pet Cemetery. It never said it was only dead animals, since animals are unable to vote, Bob only put as many names as possible.
- Much of the episode is based on the Watergate scandal and borrows many elements from the film All the President's Men which focused on the investigation into the incident by Bob Woodward and Carl Bernstein. These include the meeting with Smithers and the overheard shot of Lisa in the library.
- Bob's aides are parodies of Richard Nixon's advisors during Watergate, H. R. Haldeman and John Ehrlichman.
- Bob runs a campaign advertisement against Quimby which is largely based on George H.W. Bush's "Revolving Door Ad," an extremely important event in the 1988 US presidential campaign.
- Quimby's appearance at the debate impersonates Nixon's appearance at the 1960 Presidential debate after he had just recovered from a cold.
- Birch Barlow is a parody of conservative talk-show host Rush Limbaugh.
- The title is a reference to the film Bob Roberts, a 1992 film following the eponymous politician, suggesting that success comes from shady deals, hypocrisy and deceit. Bob enters the meeting wrapped in an American flag, a reference to the film's poster.
- Archie, Jughead and Reggie from the Archie Comics throw Homer out of their car, while Moose says, "Duh, stay out of Riverdale!" It is not known how he met them or what he did to offend them (and presumably the community they lived in).
- Homer later refers to them again; he is seen reading an Archies comic and comments, "Riverdale punks, think they're too good for me!"
- In court, Bob says, "You want the truth? You can't handle the truth!" A reference to a line from the movie A Few Good Men starring Jack Nicholson.
- Birch Barlow mentions the cartoon spokesperson Joe Camel.
- Springwood Minimum Security Prison is a parody of Allenwood Minimum Security Prison.
- Sideshow Bob gives his acceptance speech underneath a giant poster with a picture of himself on it; this is a reference to the campaign speech scene in Citizen Kane.
- In Season 2, Mr. Burns did the same thing when running for Governor in Two Cars In Every Garage And Three Eyes On Every Fish.
- Bart reveals his other enemy to be Dr. Demento, a real life radio host famous for his partnership with "Weird Al" Yankovic, a partnership that is the reason for Yankovic's fame.