: Bob escapes from a minimum-security prison and threatens to detonate a nuclear bomb unless Springfield abolishes television.
: Bob is a master of manipulation. In "Cape Feare," he successfully convinced the parole board that his "Die Bart, Die" tattoo was actually German for "The Bart, The". sideshow bob in jail
: In " Sideshow Bob Roberts ," he used his prison connections and talk radio influence to get released and successfully run for Mayor of Springfield. : Bob escapes from a minimum-security prison and
Ultimately, Sideshow Bob in jail represents the ultimate sitcom stalemate. He cannot truly be reformed, and he cannot truly succeed. The bars of his cell serve as a reset button for the series, holding him in stasis until the next time Springfield needs a touch of high-stakes villainy. As long as Bart Simpson is breathing, Sideshow Bob will continue to pace his cell, plotting a masterpiece of revenge that will, inevitably, land him right back where he started. : In " Sideshow Bob Roberts ," he
Robert “Sideshow Bob” Terwilliger Institution: Springfield State Penitentiary (Maximum Security Wing) Reporting Period: Post-Multiple Arrests (Terrorism, Attempted Murder, Grand Theft, Parole Violations) Status: Frequent Repeater (Intermittent)
Sideshow Bob rarely stays in jail for his full sentence. His releases usually fall into three categories: