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„The Simpsons: Sideshow Bob’s Complete Backstory Explained“

The Simpsons have earned a couple of enemies in 30 years, most notably Sideshow Bob, who has tried to kill Bart Simpson many times – but who is Sideshow Bob and what was his life like before he became Bart’s nemesis? Created by Matt Groening, The Simpsons debuted as a half-hour prime time show in 1989 and recently celebrated its 30th anniversary. The series is the longest running American sitcom and is currently enjoying its 31st season, with a 32nd one already confirmed.

In all these years, viewers have met not only the Simpsons family but also other notable citizens from Springfield, both good and not so nice. A recurring antagonist in the series is Sideshow Bob, who has some unfinished businesses with the Simpsons, specially Bart. His first appearance was in season 1’s episode “The Telltale Head”, but it wasn’t until later in the season, in the episode “Krusty Gets Busted”, that he got an antagonist role – and it’s in that same episode where he’s hatred for Bart began, as he exposed him for framing Krusty the Clown.

Since then, Sideshow Bob has appeared in various episodes, sometimes as main character, and others in flashbacks or cameo appearances. When thinking about Sideshow Bob, the first thing to come to mind are his plans to kill Bart, but there’s a lot more to him than that, and the series has shared some details about his backstory.

Robert Underdunk Terwilliger Jr, a.k.a. Sideshow Bob, is the son of Dr. Robert Terwilliger and Dame Judith Terwilliger, a retired Shakespearean actress. Bob’s parents have appeared in only one episode (season 19’s “Funeral for a Fiend”), though his mother was mentioned in previous ones. Bob has a younger brother, Cecil, who was constantly ignored by his parents and compared to Bob. Cecil’s dream was to become Krusty’s sidekick, but his audition didn’t go as planned and Krusty instead hired Bob on the spot, even though he wasn’t there to audition for the role. Cecil then entered the hydroelectricity industry, where he found his “true calling” as a hydrodynamics engineer – but because revenge runs deep in the family, he had something planned for when his brother got out of jail.

In season 8’s episode “Brother From Another Series”, Cecil hired Bob to work for his company, which was building a new hydroelectric dam along the river. Cecil’s real plan, however, was to skim money from the project, build a poor quality dam, and frame Bob for its destruction. His true intentions were discovered by Bart and Lisa, but that didn’t stop him from trying to achieve “the one thing Bob failed to do”: kill Bart, which, ironically, was stopped by Bob. Cecil’s plans to blow up the dam were also foiled by Bart and Bob, and even though this was the one time Bob wasn’t involved in any murderous plans, he was arrested along with Cecil.

Bob’s parents and brother joined forces to help him kill Bart once and for all by faking Bob’s death and manipulating the young Simpson into throwing away Bob’s “medication” for a supposed pre-existing condition. Of course, the Simpsons once more figured out their plan and the whole Terwilliger family was sent to prison, with Bob seen sitting in a corner, restrained by a straight jacket and laughing maniacally as he dreamt of sneaking into the Simpsons’ house and kill the whole family. Aside from his parents and brother, Bob has his own family as he was once married to an Italian woman named Francesca, with whom he has a son named Gino. Though Francesca (and Gino) tried to help him kill Bart, it’s been implied that they are no longer together as he has been seen making plans to date “age-appropriate women” in subsequent episodes.

As mentioned above, he was hired by Krusty by mere coincidence. Krusty wasn’t impressed by Cecil’s audition and spotted Bob in a fine suit, and ordered a “pie-in-the-face” for him. The impact knocked off Bob’s top hat, causing his hair to pop up, which Krusty found to be perfect comedic material and immediately hired him. However, Bob wasn’t aware of what being a sideshow was actually about and had to endure repeated instances of abuse on live TV, including being shot from a cannon and hit by pies. Krusty took a more sadistic route in order to get more laughs, which in turn made him more successful, but also made Bob grow tired of how he was being treated. Bob couldn’t stand Krusty and his success, and so he plotted Krusty’s downfall, which didn’t go as planned: he ended up in prison, and Krusty replaced him with Sideshow Mel.

Not much is known about Sideshow Bob’s life before his obsession to kill Bart, as that’s what his arc has been all about. Bob is a self-proclaimed genius, graduate of Yale University, and champion of high culture, which shows in the way he talks and his love for operettas. Bob spent a long time as Krusty’s non-speaking sidekick, but when he grew tired of the way he was being treated, he disguised himself as Krusty and framed him for an armed robbery of the Kwik-E-Mart. After Krusty was arrested, Bob took over the show and turned it into an educational one, introducing children to elements of high culture and including a psychological segment called “Choices”, though he kept the popular Itchy & Scratchy Show. Bart exposed Bob as the real robber on his TV show, and he was arrested, swearing revenge on Bart.

During his time in prison, Bob won an Emmy for his role on Krusty’s show, but wasn’t able to keep the award. While in jail, he took part in a prisoner dating service and met Selma Bouvier. Once he was released, he married Selma as part of yet another plan: Bob’s real intentions were to kill Selma and inherit all the money she had invested in the stock market. His plans were once again foiled by Bart, and Bob was sent back to prison – after that, he started targeting Bart directly, and continued to be outsmarted by him. Bob keeps finding a way to come back, even in non-canon appearances (most notably the segment “Wanted: Dead Then Alive” in “Treehouse of Horror XXVI”, where he finally got to kill Bart… and brought him back), and no matter how many enemies Bart gains with his pranks, Sideshow Bob will remain as his one and only true nemesis.

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