Airs: 12:00am - 12:30am on FOX
Homer has been listening to a conservative radio talk show host. One day Sideshow Bob calls in from prison, voicing his conservative views. The host, Barlow, gets Sideshow Bob released from prison. Upon Sideshow Bob's release, the town's Republicans want him to run for mayor against Quimby. Bob outwits Quimby in every debate and wins by a huge landslide. Lisa is skeptical (as usual) about how he did it, so she investigates. Meanwhile, Homer has problems with the gang from Riverdale. Sideshow Bob imposes a few new policies. For one he condemns the Simpsons' house to help make way for the new Matlock Expressway, much to the delight of the seniors. Second, he gets Bart placed in kindergarten. Lisa discovers how Sideshow Bob won the election: he had dead people vote for him. He admits to all of this when Bart and Lisa outwit him in front of the town. Sideshow Bob goes back to prison.