4. Rex Banner
In 1997 episode 'Homer vs. the Eighteenth Amendment', Bart accidentally ingests alcohol during a live news report and is shown staggering around drunk on television, leading to outrage, and prohibition being enforced on Springfield. Homer obviously isn't too happy about this and attempts to flaunt the law by taking up the alias of the "Beer Baron", smuggling booze into Springfield via bowling balls. Rex Banner replaces the incompetent Chief Wiggum as Chief of Police and makes it his life's mission to capture the "Beer Baron", but is thwarted when Homer deliberately hands himself in to Wiggum to help him get his job back. Unfortunately, Wiggum cannot prevent Homer from being punished for his beer smuggling, and the Simpson dad is almost fired out of a catapult, until Rex steps in and is instead catapulted out of Springfield, probably to his death.