Yandere Toons x Reader: An Anthology of Headcanons and Scenarios

Sideshow Bob (Platonic & Romantic Headcanons) (The Simpsons)

TW: Mentions of Violence & Death, Stalking, Workplace Abuse (not by Bob), Victim Playing, Mention of Incarceration, Emotional Manipulation, Toxic Mindsets.

A.N. - Incoming Simpsons binge.

Platonic:

With his mother's side of the family teaching him the fine art of acting, Sideshow Bob thinks of himself as sophisticated and has a plethora of knowledge about theatre that he wishes to share with his friend. The goal of this is to introduce them to what he considers a higher form of recreation and, in his opinion, enrich their mind so that they may enjoy the same indulgences as he and come to understand his questionable lifestyle. This is a source of amusement for his brother Cecil, whose taunts are deflected by Sideshow Bob's confidence that enough time and effort will change their point of view.

Sideshow Bob is a man of many grudges, and any rudeness to his friend or himself never strays far from his thoughts until his idea of worthy retribution is enacted. This commonly entails framing the culprit for a violent crime to land them a life sentence in Springfield State Prison or, if he finds a suitable way to orchestrate it, sending them to an early grave. Once he sets his sights on proving to someone the grievousness of their mistake, no mercy is offered unless his friend openly forgives them and Sideshow Bob believes that the culprit's regret is sincere.

For all his talk of minding one's manners, Sideshow Bob is easily irritated by people in his and his friend's life acting uncouth and failing to meet his standards for companionship. There is little hesitation when he starts to curse their name and dub these so-called simpletons a stain on his friend's legacy. He does not understand any complaints they may offer, for he has no enduring loyalty to anyone outside of his friend, his family, and a few dead poets.

Romantic:

In public spaces, Sideshow Bob wears a carefully crafted mask of innocence. The friendliness he displays towards his partner is genuine, but the compliments and pleasantries he pays to everyone else are a thin step short of condescending and threatening. If his partner is giving lukewarm responses to his conversation about classical literature, Sideshow Bob allows some bitterness to creep into his attitude before he attempts to regale them with flawless recitations of whole acts from H.M.S. Pinafore and Macbeth.

A penchant for theatre and cosmopolitan interests runs in the family, and Sideshow Bob is a prolific fan of disguising his mission to endear himself to his partner's colleagues as nothing more than a harmless want to make friends. He feigns affability and plays the victim until the day he rigs an explosion in the target's room or ambushes them in an isolated location. Any trace of incriminating behaviour is evaded until, in the heat of a Shakespearean monologue at either the crime scene or the funeral, he makes a cruel joke about the method of death or a spiteful comment about the departed.

While not a miser or a poser by any means, Sideshow Bob obeys a code of ethics that is based on his wealthy upbringing and his own ideas of civility. He despises impropriety and has high expectations for his partner, wanting them to conduct themselves as he would conduct himself. His mistreatment as the sidekick of Krusty the Clown has ruined his capacity for patience, but Sideshow Bob directs his frustrations and homicidal impulses at those who he accuses of leading them astray and exerting bad influences on their behaviour.