This is the first and only Sideshow Bob episode that Chief Wiggum, Eddie, and Lou don't appear, to arrest Sideshow Bob.
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.
Syndicated prints and FXX reruns of this episode, including the Complete Sixth Season DVD print, skips the whole intro, meaning that it goes from the "P" of the title screen to the "Created By/Developed By" TV credits. This same intro was used five seasons earlier on some prints of "Life on the Fast Lane", and returns in HD twenty seasons later in "The Musk Who Fell to Earth".
In FXX airings, there is a slight cutoff when the "P" goes to the TV credits, as the TV moves up while the "P" moves, showing that FXX seems to paste the same TV credits onto intros.
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, and so is the house (even if it 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.
Although Sideshow Bob was established to have won the election by rigging it via deceased voters, the scenes of the people casting their votes showed Homer and Krusty (people who Bob antagonized before) voting for Bob, implying that Bob would have won the election regardless.
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, while his first name is a possible reference to the far-right John Birch Society.
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.