9. Becoming Mayor
The 2005 Simpsons episode, "The Italian Bob", was a rare one for Sideshow Bob in that he was stripped of all the traits fans had grown accustomed to - the elaborate scheming, plots to kill Bart and murderous blood lust were rarely seen here. After being tasked to pick up a new car by his boss, Mr Burns, Homer takes his family to Italy, where they discover the mayor of a small Tuscan village is none other than Sideshow Bob. Bob seems peaceful at first, seemingly enjoying his life away from Springfield, and is even married with a small child. But his new-found bliss goes out the window when Lisa informs the villagers of Bob's criminal past. That's when we begin to see the real Sideshow Bob we all know and love, as both he, and even his family, swear to kill the Simpsons, before Bob is (naturally) foiled. What we loved about this particular Sideshow Bob moment is that his devious ways appeared to rub off on his son, along with the malicious grin, and all.