Episode - 2F02\\
First Aired - 10/9/1994

With help from the Rush Limbaugh-esque Birch Barlow (a right-wing radio personality), Sideshow Bob gets released from prison again and runs for mayor against "Diamond" Joe Quimby -- and Bart and Lisa investigate how one criminal running for public office got so many votes while another criminal got so few.
!!This episode contains examples of:
* ZeroPercentApprovalRating:
-->'''Kent Brockman:''' The results are in: for Sideshow Bob, one hundred percent; and for Joe Quimby, one percent. And, we remind you, there is a one percent margin of error.
* AccuseTheWitness: Bart and Lisa get Bob to confess by accusing him of being Barlow's front man. He immediately produces several binders and floppy disks detailing his "masterpiece of electoral fraud".
* AsHimself: Creator/DrDemento; Larry King
* BitingTheHandHumor:
-->'''Larry King:''' Now, a word to our audience: even though we're being broadcast on...Creator/{{Fox}}, there's no need for obnoxious hooting and hollering. ''(The audience does just that; King groans.)''
* BrickJoke: The bats in the public library.
** Homer gets thrown out of Riverdale for reasons unknown. When he drives Bart and Lisa to meet the unknown informant in the parking garage, Homer stays in the car, reading ''Franchise/ArchieComics'', muttering, "Lousy Riverdale punks! Think they're too good for me."
* TheCameo: Archie and his pals Jughead, Reggie, and Moose from the Archie comics make a cameo, throwing Homer from their vehicle and telling him to "Stay outta' Riverdale!"
* CassandraTruth: Bart telling Marge that he was told to bring in fireworks.[[note]][[FridgeLogic Given Bart's history, one would think Skinner would personally tell Homer and Marge about the project]].[[/note]]
* DevilInPlainSight: The reaction to Bob's below-mentioned evil laugh? "And just look how happy he is!"
** If you hear well, it sounds like everyone is laughing with him.
* DickDastardlyStopsToCheat: Bob goes for ballot-stuffing in an election where Quimby may have actually had a ZeroPercentApprovalRating.
* EvilLaugh: Sideshow Bob, of course, delivers a long, utterly hammy one after he wins the election.
* {{Expy}}: As noted, Birch Barlow is one of real-life conservative radio personality RushLimbaugh.
* EvilIsPetty: As soon as he is elected, Bob uses his power to make the Simpson family as miserable as possible, planning to mow down their house to make room for the new Matlock Expressway, and sending Bart to kindergarten (being a class flunky however, he only ends up enjoying this).
* {{Homage}}: The entire second act, including the bird eye shot of Lisa studying in the library, is an homage to Film/AllThePresidentsMen.
* HornedHairdo: Quimby inadvertently sports one during the mayoral debates after he runs his fingers through his sweat-soaked hair, leading the news team to electronically demonize him in their broadcast.
* HypocriticalHumor
-->'''Announcer:''' Mayor Quimby supports revolving door prisons. Mayor Quimby even released Sideshow Bob, a man twice convicted of attempted murder. Can ''you'' trust a man like Mayor Quimby? Vote Sideshow Bob for mayor!
** Also, Homer had earlier in the episode stated a low opinion about people who vote but he's later seen voting for Sideshow Bob. (He approved Bob's "Selma-killing policy".)
* InsaneTrollLogic: Sideshow Bob runs on this, as seen in his aforementioned campaign ad.
-->'''Sideshow Bob:''' I am presently incarcerated. Convicted of a crime I didn't even commit. "Attempted Murder", now honestly, what is that? Do they give a Nobel Prize for "Attempted Chemistry"?
* ITakeOffenseToThatLastOne
-->'''Birch Barlow:''' There are three things we are never going to get rid of in this town. One, the bats in the public library; two, Mrs. [=McFuly=]'s compost heap; and three, our six-term mayor - the illiterate, tax-cheating, wife-swapping, pot-smoking spendocrat, Diamond Joe Quimby.
-->'''Mayor Quimby:''' ''(as he's watering a marijuana plant in his office)'' Hey, I am no longer illiterate!
* ItsPersonal: Lisa states this after finding out one of the dead people and pets that "voted" for Bob was her long-deceased cat, Snowball I. Bart, understandably takes offense at this:
-->'''Bart:''' Um...he ''did'' try to kill me!
* LaughingMad: Bob, after being elected mayor.
-->'''Kent Brockman:''' [[ComicallyMissingThePoint And look how happy he is!]]
* LighterAndSofter: Compared to the previous Sideshow Bob episodes. "Sideshow Bob Roberts" is more of a humorous political satire where Bob doesn't try to murder anyone.
* TheManBehindTheMan: Played with when Bart and Lisa shift the accusation of the rigged election to Birch Barlow in order to get Sideshow Bob to confess.
* MadeOfIron: Homer somehow was able to cushion a wrecking ball from hitting its house (similar to what happened on ''The Simpsons Movie'', only Homer actually felt pain when he hit [[VisualPun the rock and a bar called "A Hard Place"]]. On this episode, Homer doesn't even flinch).
* NoodleIncident / RiddleForTheAges: What did Homer to do to [[PersonaNonGrata get thrown out of]] [[Franchise/ArchieComics Riverdale]]? Better yet, how'd he get there in the first place? And what did Bart do to gain the enmity of Doctor Demento?
* PasteEater: When Quimby and Bob come to Springfield Elementary:
-->'''Skinner:''' Now, students, I want you to be on your best behavior for this carefully-choreographed media event. Now this means there is to be no wising-off, no face-making, and no grass-eating. This means you, Ralph.\\
'''Ralph:''' ''(mouth full of grass)'' Yes, sir.
* RealityIsUnrealistic: As it turns out, graveyard votes, votes cast by people who are deceased, was a common form of fraud.
* SingleTargetSexuality: Subverted. Smithers alludes to being gay when in previous episodes, it was heavily implied that he was either sexually confused or straight, but had a crush on his boss.
* ShoutOut:
** Politicians using the votes of people who passed away happened earlier in American history.
** Quimby and Sideshow Bob's TV debate is a reference to Kennedy and Nixon's 1960 TV debate.
** Sideshow Bob posing in front of his election poster references ''Film/CitizenKane''.
** The entire second act is a parody of the Watergate scandal, specifically spoofing ''Film/AllThePresidentsMen''.
** The commercial described in HypocriticalHumor is a parody of the infamous "Willie Horton" advertisement by the UsefulNotes/GeorgeHWBush campaign during the 1988 presidential race.
** The episode's title is a reference to the satirical political mockumentary ''Film/BobRoberts''.
* SpecialGuest: Henry Corden as Fred Flintstone[[note]]The voice on the Flintstone phone.[[/note]]; Creator/KelseyGrammer as Sideshow Bob; Creator/PhilHartman as Lionel Hutz
* SuspiciouslySpecificDenial: A TV ad for Quimby ends with: "It's not the mayor's fault that the stadium collapsed!"
* TakeThat: This is the first time the show really takes stabs at the Republican Party, which garnered a lot of complaints from viewers ([[http://snpp.com/episodes/2F02.html particularly the ones on snpp.com]] who were used to seeing the show skewer both political parties (or only focus on local politics and not national stuff). Of course, considering that Mayor Quimby is the episode's representative of the Democratic Party, it does even out somewhat.
** Of course, even though the episode was meant to spoof both Democrats and Republicans (but especially Republicans, as Creator/MattGroening is a left-leaning Democrat), he admitted this episode [[MisaimedFandom did attract many right-wingers who wished for him to become a member of their political groups/organizations.]]
** Also disappointment was expressed in the DVD Commentary of the episode that Lisa would listen to "St. Elmo's Fire".
* TitleOnlyOpening: The second FOX airing and the DVD version goes from the ''Simpsons'' cloud title straight to the executive credits on the TV, while the original airing and the syndicated version had couch gags that were used other episodes (the original airing had the couch gag from "Boy Scoutz 'n The Hood"[[note]]the one where the Simpsons' eyes are floating in the dark[[/note]] while the syndicated version had the oft-used one from "Rosebud"[[note]]the one where The Simpsons run in and find an identical version of themselves on the couch[[/note]]). This is one of the few times they did this after season one and before the high-def episodes from season 20 on (barring the special episodes, like the ''Treehouse of Horror'' episodes and the two Troy [=McClure=]-hosted episodes: "The Simpsons 138th Episode Spectacular" and "The Simpsons Spinoff Showcase.")
* YouCantHandleTheParody: "...No truth handler, you! Bah, I deride your truth-handling abilities!"