The Simpsons: Every Sideshow Bob Episode Ranked Worst To Best
11. Gone Boy
This season 29 entry is bolstered significantly by a focussed plot and a deep dive into the psyche of Springfield’s least successful criminal. Bart falls down a manhole into an abandoned military base, and Bob, serving time on a nearby chain gang, joins the hunt, dead set on offing his young foe once and for all.
The majority of the story is told from Bob’s perspective, and is all the better for it. Grammer has put far more effort than necessary into the development of the character over the years, and he sells Bob’s sense of loss brilliantly. Bart is believed dead, and as such Bob’s life has little purpose.
When Bob eventually tracks down the still-living Bart, he has the chance to kill him, but ultimately decides against it. The decision to take the character in a different direction works well here - the writers had toyed with Bob giving up evil before, but tended to revert to the norm. The choices here serve well to keep the character fresh.
Combined with some strange but enjoyable spoofs of Saul Bass iconography, this is a strong chapter in the continuing saga of Sideshow Bob, breathing new life into the character, if only briefly.