The Simpsons: Every Sideshow Bob Episode Ranked Worst To Best

Bob’s status as a Springfield villain was established in his debut appearance, but Black Widower is where the writers really figure out the formula going forward. With Grammer’s silky intonations giving the character some real gravitas, early instalments played out like mini-film noirs, with Bart in the role of the hard boiled detective looking to crack the case before it was too late.

Black Widower is perhaps the best pure whodunnit - or rather, howdunnit - of the bunch. We know that Bob is up to no good, planning on murdering his new bride, Selma. All the pieces are laid out for us to solve the mystery, should we wish to do so.

It’s also the start of Bob’s descent into pure villainy. Whereas his initial crime was understandable, given his shabby treatment at the hands of Krusty, here he’s simply out for a payday. His second foiling at the hands of a 10 year old triggers his lust for revenge, and the many great episodes yet to come.

Season three of The Simpsons is where things really pick up, and this great entry into the lore of Sideshow Bob is emblematic of the show’s blossoming.