Lisa studies Mayor Quimby's reelection campaign for a school project. While listening to a call-in talk show hosted by ultra-conservative Birch Barlow, she recoginizes the voice of one of the callers: Sideshow Bob. Bob has an instant rapport with Barlow, who makes Bob's release from prison his top priority. Bart is horrified that his arch-nemesis is manipulating the madia in hopes of winning his freedom. As support for Bob's release grows, Mayor Quimby grants him a pardon.

Backed by members of Springfield's Republican elite, Bob announces his candidacy for Mayor. A game of one-upmanship ensues between Bob and Mayor Quimby. When Quimby ingests too many flu caplets just before a televised debate with Bob, his poor performance leads to Bob's landslide victory.

The moment he assumes power, Bob condemns the Simpson home to permit the construction of a new expressway. Convinced that the election is fraudulent, Lisa and Bart discover that many voters who cast their ballots for Bob are dead. Lisa tricks Bob into admitting that he rigged the election. He is arrested and sentenced to serve time at a minimum security prison.

Black Widower

Cape Feare

Sideshow Bob Roberts

Sideshow Bob's Last Gleaming

Brother From Another Series