Sideshow Bob Roberts (S06, E05-108)

"And just look how happy he is!"

Plot Summary
Seems I'm a bit late with this episode, a somewhat satirical take on politics both then and now, but more importantly than that its another Sideshow Bob episode.  Bob, still in prison after his attempt on Bart's life, calls into a right-wing radio show hosted by Birch Barlow, complaining that his incarceration for "attempted" murder has no merit.  Birch makes it his mission to free Bob, gathering a large public force to convince Mayor Quimby to let Bob go.  Quimby relents, and quickly Bob is released from prison.

With the race for mayor coming up, the Republican party, consisting of Barlow, Mr. Burns, some Texan, Ranier Wolfcastle, Dr. Hibbert and who I presume is Dracula, agree that Bob would make an excellent candidate to unseat the six-time incumbent Quimby.  Bob's campaign is harsh and quick, using his own release from prison as a weapon against Quimby.  In a debate, Quimby is suffering from a cold (and extra-drowsy cold medication) and is unable to keep up with a witty Bob.  Come election time, Bob earns 100% of the vote to Quimby's 1% (with a 1% margin of error) and Bob gleefully enjoys his victory.

Soon, Bob makes efforts to make life miserable for the Simpsons, Bart in particular.  The "Matlock" Expressway, a new highway initially proposed by Quimby to appease seniors but left in limbo during the campaign, is quickly being built by Bob but requires going straight through the Simpson house, leaving is to be demolished.  Bob also sends an executive order to send Bart all the way back to kindergarten.  Lisa is convinced that Bob did not win legitimately given the wide disparity of votes between two ex-convicts, and begins to investigate, easily acquiring the list of people who voted and for whom.  Falling asleep in her attempt, a shadowy figure gives Lisa a letter to meet at a Pay & Park & Pay.  Homer unwittingly reveals the figure to be Smithers, whose "lifestyle choices" are conflicted with Bob's ultra-conservative views, tells the kids to look for one name: Edgar Neubauer.

The search for Edgar is fruitless at first, but Bart finds a gravestone with his name.  Lisa then realizes that most of the votes for Bob were by the deceased, including most of the pets in the pet cemetery.  Having found evidence of voter fraud, they take Bob to trial.  There, Lisa recognizes Bob's ego and attempts to cast Barlow as the mastermind behind the fraud scheme, implying Bob was nothing more than a puppet.  Bob furiously refutes that claim and takes full responsibility for the fraud, including showing the court all of the evidence needed to convict himself.  Having been trapped, Bob is arrested, and things go back to normal with Quimby somehow getting back in.  Bob in the meantime is sent to a minimum security prison where rowing contests against Princeton alums is a thing.

Quick Review
For an episode that tries to be a Sideshow Bob episode and a political satire, the combination works very well here, and there was a lot of humor to supplement the plot.  Oddities, like Homer's newfound rivalry with the Riverdale gang and the Matlock expressway add to the episode's quality as well.

Final Score: 9.5