The Simpsons: Every Sideshow Bob Episode Ranked Worst To Best
3. Sideshow Bob Roberts (Season 6, Episode 5)
The Simpsons has always had a rocky relationship with political satire, but Sideshow Bob Roberts is living proof it can pull it off when it wants to.
This time around, Bob's a free man once more, and has decided to run for Mayor of Springfield, something which works profoundly well as Bob charms the locals into falling for him head-over-heels and commits widespread election fraud.
With sharply amusing references to the Watergate Scandal, the rise of populism, All the President's Men and Citizen Kane, Sideshow Bob Roberts bursts with intelligence from the first frame, but never loses sight of the Bob/Bart feud that drives much of the former clown's story.
As it stands, Sideshow Bob has never been this devious or successful in his quest for power and recognition.