Here is a chronological guide to the essential episodes featuring Springfield’s favorite antagonist. The Foundation: The Early Years
Sideshow Bob endures because he is more than a cartoon villain. He is a tragic figure—a brilliant man undone by his own pride and a pathological need to murder a fourth-grader. And somehow, after 30+ years, we still cheer when he steps on that rake.
Bob returns with a reformed image and marries Selma Bouvier. His true goal—killing her for her retirement fund—is thwarted by Bart’s detective work. This episode cemented Bob’s character as a "high-culture" villain who loves Gilbert and Sullivan and fine wine. The Golden Era: Peak Bob
The Simpsons travel to Italy, where Bob has become the respected mayor of a small town. He has a wife (Francesca) and a son (Gino). For a brief, beautiful moment, he is happy. Then Bart, drunk on wine, reveals Bob’s past as a would-be murderer.
In this episode, Sideshow Bob returns to Springfield after being released from prison. He becomes obsessed with Marge's new Indian neighbor, Professor Hampster, who bears a striking resemblance to his former tormentor, Professor Frink. The episode features Sideshow Bob's signature wit and schemes, as well as some clever references to his past escapades.