The 15 Most Heinous Acts Committed By The Simpsons' Sideshow Bob

The Simpsons have been gracing TV screens the world over with good humour, makeshift morals, and diabolical deeds for nearly thirty years now. Some might debate the notion that the show still produces

The Simpsons have been gracing TV screens the world over with good humour, makeshift morals, and diabolical deeds for nearly thirty years now. Some might debate the notion that the show still produces good humour, or morals of any kind. In fact, many say that the show lost its touch as early as season eleven. But for many people, even if all they watch is that first wonderfully devious decade, the Simpsons are a hilarious family with which one can escape from every day drudgery for a while.

This family is not without its hardships though, of course. Aside from never being too well off, having some rather mischievous kids, a blubbering drunk and abusive father, and an incredibly repressed mother, there are darker, outside influences that do manage to bring the family together from time to time.

Sideshow Bob Terwilliger (made famous by Kelsey Grammer) is one such case. Since framing Krusty the Clown, and getting caught by Bart and Lisa, there has been a homicidal chip on Bob's shoulder for one Bart Simpson. And to be sure, not all of his diabolical schemes are based around Bart, but they typically have some sort of "Bart-killing policy", or revolve around killing someone in his family.

15 Bob Runs For Mayor

Calling a press conference to call out the local government about his treatment in prison, Sideshow Bob is released and, in turn, decides to run for mayor against Quimby. Now Diamond Joe Quimby was never a good mayor, and slept and paid his way to his position, but the people fall for Bob. Though Quimby wins the Retirement Castle by calling the new expressway the Matlock Expressway, Bob does one better by agreeing to that term, and by listening to the old folks' problems the rest of the afternoon. Bob even manages to sway Homer and Krusty to vote for him, in spite of the fact that he tried to kill Homer's son, and frame Krusty for robbery. Bob wins and declares that the Simpsons must move by the time the Matlock reaches their home, or the home (and anyone left in it) will be destroyed. Thankfully (depending how you look at it), some of Bob's laws are enough to push Smithers to help Bart and Lisa discover the truth about Bob's campaign. Using the dead of Springfield (including Snowball and the rest of the Pet Cemetery) to ensure a landslide victory.

14 Bob Turns Bart Into A Bomb

Announcing his fifth and final retirement, due to annoyance with executives, Krusty goes on air with Kent Brockman to talk about it. Mentioning that he has taped over all of the archival footage from the Sideshow Bob era with episodes of Judge Judy, Krusty seals his fate. Bob, watching the confession, begins forming another diabolical plan: to kill two birds with one stone...or one little boy anyway. When first confronted by Bob, Bart is not at all afraid, knowing by now that Bob is caught by the cops in the end anyway. So this time, Bob hypnotizes the little boy, and after sending him to destroy a statue of Krusty, then straps him full of plastic explosives and takes him to Krusty's retirement show. Sent out onto stage to receive a hug from Krusty, thereby setting of the explosives, Bart starts on his way to meet his maker (no, not Matt Groening). However, after Krusty admits his feelings of guilt and his fondness for Sideshow Bob, Bob gets his monkey to remove the explosives, and throw them into the executives' office (but they reform like the T-1000). In the end, the sideshows, Krusty, and the Simpsons sit to a meal, whereupon Bob is caught by the police and sentenced to death by guillotine. The execution is soon cancelled, but to be fair...he turned a boy into a bomb and blew up several TV executives.

13 Bob Threatens Nuclear Destruction

All because of a ruined model of Westminster Abbey, Bob lashes out about network television (particularly the FOX network— which is understandable). Bob just happens to be on work placement from prison at the local airfield where they are gearing up to hold an annual airshow. Impersonating a Colonel, Bob finds his way into a restricted area, and gets his hands on a ten megaton nuclear bomb. Making demands from the privacy of a stolen DUFF blimp, Bob orders Springfield to dispose of TV for good, lest he detonate the warhead. Krusty however, determined to stay on the air, finds a broadcast shed, and begins to transmit a very shoddy television program (now being the only show in town). Bob mourns as he discovers that nuclear annihilation is no match for TV. Attempting to detonate the bomb, Bob finds it is a dud, but takes Bart hostage, steals the Wright Brothers' plane, and aims to fly it into Krusty's broadcast shed. Simply bouncing off the shed, Bob is once again captured and taken into custody.

12 Bob Frames Krusty For Armed Robbery

Well here it is. The very beginning. All those years ago, when Krusty canned Sideshow Bob, recruited Sideshow Mel, and continued producing crummy TV. Sideshow Bob, entering the Kwik-E-Mart dressed as Krusty the Clown, commits armed robbery. Homer dives out of the way, very gallant in his aid to store clerk Apu, and the whole thing is caught on camera. Showing it all on TV, homer is embarrassed, but still pulls himself together to show Bart that his hero is truly a criminal. Meanwhile, Bob takes over Krusty's show with healthy, educational, touching, and engaging programming. He is actually the best thing to ever happen to Springfield, in this regard. However, unwilling to give in to Sideshow Bob, and recalling a clip of "Krusty" getting his massive foot stepped on, Bart reveals that Bob is the true culprit. Bart, being such a huge fan of Krusty, and a great collector of clues (with the help of Lisa), knows that Krusty can't read, and also has tiny feet. The "Krusty" at the Kwik-E-Mart read a magazine before having his foot stepped on. Pointing out Bob's huge intellect and feet, the young Simpsons have Krusty released, and Bob sent to prison...which started the whole thing.

11 Bob Marries And Attempts To Murder Selma

Getting out of prison, how almost every episode with Bob begins, Bob doesn't seem to gripe with Bart much, though there are dark glimpses of possible intentions. Instead, Bob is brought to the Simpsons' house for dinner via Aunt Selma, who met him through a "prison pen-pal club". Understandably upset by this Bart does all in his power to break the relationship, and subsequent wedding (as Bob proposes that very night at dinner). Unable to steer Selma clear of the maniac, Bart sulks, only to be tipped off by certain clues, and an episode of MacGyver, that Sideshow Bob plans to murder his Aunt Selma. Bart managed to piece together Bob's plan through the following clues: 1) Selma permanently lost her senses of taste and smell, 2) Bob wanted a room on their honeymoon with a fireplace (gas powered), 3) Selma quit smoking except after meals and after MacGyver, 4) Bob hated MacGyver. Surmising that Bob would leave the gas run, unbeknownst to Selma, while she watched her show, and subsequently lit up a smoke, he rushed to save her. As the room explodes (thanks to the incompetence of Chief Wiggum), Bob returns to discover Bart and the police waiting for him. Foiled again.

10 Smoking Kills

This heinous act belongs to both Sideshow Bob and Homer Simpson. True, in the episode that the above clip is from, Bob sends death threats written in his own blood to Bart...but on the other hand, so too does Homer (just not with his own blood). And later in the episode Bob does try to kill the little scamp yet again, but this is still not the heinous crime here. Going out as a family to see an Earnest movie, the Simpsons are disturbed by the ridiculous laughter of some obnoxious figure in front of them (how they don't know right away that it's Sideshow Bob is laughable, but there it is). Being obnoxious and causing a raucous in the middle of a film at the cinema is crime enough, but in addition to that, Bob is smoking! Not only smoking, but smoking a cigar, which is the equivalent of smoking five cigarettes (if the Bouviers are to be believed). And as aforementioned, Homer is complicit in this heinous act as well, since he has a far larger cigar, and a much louder guffaw during the film.

9 Bob Finally Kills Bart...And Has Some Fun

Everyone knew that this was going to happen at some point. But also, everyone knew it could only happen under the banner of a Treehouse of Horror episode. And so, in Treehouse of Horror XXVI, twenty four years after his desire for Bart's blood began, Sideshow Bob confronted the little boy at school. Wielding a harpoon gun, Bart is momentarily frightened at the appearance of his nemesis, but then, as before, he shrugs him off. Dancing about like a hooligan, Bart sings about how Bob wouldn't be able to hit him even if he put an x on his head. That being said, Bob does not hit Bart's head, but plunges a harpoon right through the little boy's heart. Sure that Bob made some mistake Bart carried on a little longer, then realizes he is mortally wounded. Collapsing to the floor, he asks only that Bob tell Homer for him that he is fat. Bob, victorious, then uses the boy's intestines for a scarf, plays mini-golf with Bart's mouth, and generally throws and poses him around. A bit morbid for The Simpsons, Bob finally gets his victory...though of course it is short lived.

8 The Italian Bob

Picking up a new Italian sports car for Mr. Burns, the Simpsons go to Italy. Touring around, a giant wheel of cheese lands on the car (cheese-related incidences is the only coverage the car does not have). Coming to a small village, the Simpsons are pointed toward the mayor of the town who is none other than Sideshow Bob. Pleading with the Simpsons, Bob asks that they say nothing of his criminal past. Wanting to forget the past and having started a new life, crushing grapes for the locals with his huge feet, and eventually becoming mayor, Bob begs. The family agrees in exchange for their car to be fixed. Unfortunately, after Lisa has a bit of wine in her, she gets talkative, and mentions Bob's past. Stumbling back, she pulls on Bob's outfit which (for some ridiculous reason) reveals a Springfield Prison uniform. Losing everything, Bob swears "Vendetta" on the entire family. Even Bob's wife and son join him on his murderous revenge seeking. Saved at the last minute by Krusty, who was bombing an Italian opera, the Simpsons flee as Bob's family walk away with evil grins...Bob raised a family of psychos as well.

7 "Python Jaw, Unhinge!"

Yeah...he tries to eat Kearney. As discussed above, Sideshow Bob becomes Chief Scientist for Monsarno GMO. What was not mentioned from this episode, is that there is a side plot where Marge starts an abstinence club, showing teens the most horrible way to stop simply not having sex. This, to no one's surprise, turns the group of teens into an agitated and destructive bunch. As Bart and Lisa plea for Bob to sing before he kills them (yet again), Homer and Marge show up with the sexually frustrated crew. Telling the teens that she release them from their pledge of abstinence if they stop Sideshow Bob, Marge sicks the violent group of teens on Bob. Knocking a couple aside, Bob grabs hold of Kearney, unhinges his genetically enhanced, python jaw, and begins to consume the portly teen. It is not until Lisa comes up, as said before, with some Walt Whitman, that Bob tosses Kearney aside and jumps into the lake to his death...until he recalls the gills. Cannibalism is a new low for Sideshow Bob.

6 From Outlaw To Legend

Kent Brockman said it best: “America has a tradition of turning outlaws into legends after their deaths: Billie the Kid. Bonnie and Clyde. Jesus Christ. Joining them now is Robert 'Sideshow Bob' Terwilliger.” That's right, Bob dies...but not really. After a restaurant hoax to lure the Simpsons to their deaths, Bob is foiled by a misquote of Shakespeare. At trial, Bob pulls a vial of nitro for his heart condition, but before he can consume it, Bart flings it out the window, whereupon Bob has a heart attack. At the funeral, the town of Springfield turns on Bart, who is then urged by Cecil to pay his respects to Bob at the funeral home. As he stands by the coffin, Bob springs out, throws the boy in, and begins the conveyor belt and furnace. The Simpsons storm in (as Lisa put the clues together) and Homer blinds Bob with some hobo ashes. As it turns out, the misquoted Shakespeare at the very beginning was all part of the plan, where Bob's entire family came together, simply to incinerate Bart.

5 Bob Sings Gilbert & Sullivan

The Simpsons move away from Springfield (leaving Grandpa behind without his pills, and with wolves after him) to Terror Lake, escaping the very public threats of Sideshow Bob on Bart's life. Of course Bob straps himself to the Simpsons' car and travels along with them. After being driven through a cactus patch, stepping on several rakes, and being crushed by a parade of elephants, Bob shakes the cobwebs and captures the Simpsons, tying them all up, save for Bart (Homer sleeps through this whole thing). Running from end to end of the boat, the lake laden with eels and alligators, Bart is trapped by Bob, who comes at him with a sword. Cuing the first request for Bob to sing before murder, Bart convinces the maniac to sing the entire score from the H.M.S. Pinafore. Treating Bart to an extravagant show with costumes and vocal changes for each character, Bob finishes and makes to kill Bart. Running aground just by a brothel that the police happened to be...investigating, Bob is foiled again.

4 Bob Inspires Art Like This...

This might be the most heinous act of all that Sideshow Bob has done. His dastardly deeds in The Simpsons are at least relegated to a TV cartoon. But this...this is perhaps the most tame of the very bizarre fan art that has been done of Sideshow Bob Terwilliger. It's absolutely disgusting, some of the pictures. Of course there is weird stuff all over the internet and Bob is certainly not the only Simpsons character to get this bizarre, and overtly sexual treatment, but he features heavily...with Marge, with Willy, with Patty and Selma...the sexual deeds one never thought possible; that one never, ever dreamed about, or even had the slightest thought about...It has always been known that the internet was full of dark recesses, from which very disturbed, and disgusting people appear, but to tarnish The Simpsons brand with such graphic, tasteless, and bizarre work...Perhaps it is true that it takes all sorts to build a community...and there's a reason why some people are just brushed aside.

3 Bob Unwittingly Outshines His Brother

Bob Terwilliger was never interested in becoming a sideshow. That was his brother Cecil's fantasy. Since he was a child Cecil wanted to be a part of the Krusty the Clown Show. Even going so far as to spend four years in "Clown College" to prepare himself, to which Cecil says, "I'd thank you not to refer to Princeton that way". Come time for his audition, Krusty and the producers have no interest in Cecil's performance. Ordering a pie in the face, upon spying Bob however, Krusty bursts out laughing and hires Bob on the spot. Never getting over how his brother stole the limelight from him, Cecil disappears...until of course Bob is released from prison. Cecil hires his brother on to work for him at the hydro dam, as Cecil is the "Chief Hydrological and Hydrodynamical Engineer". Truly, Cecil simply wanted to frame Bob for destroying Springfield by way of blowing up the already weakened dam, getting his revenge at long last. In the end, Bob saves the day and is put back in jail, but it was Bob who started Cecil on his quest for revenge in the first place. Considering how little Bob has appeared on The Simpsons, he really has done some damage.

2 The Man Who Grew Too Much

Under the guise of having given up evil, Sideshow Bob becomes the Chief Scientist at Monsarno, an obvious play on a real-life GMO food production company. Lisa discovers that GMOs (genetically modified organisms) are actually good for everyone and while she is shocked, demands to meet with the company's chief. Enter Sideshow Bob, who makes nice with Lisa, promising that they can meet and talk about fine art and such things that Lisa yearns to talk to someone about. Strolling through a museum together, Bob saves Lisa from some falling objects and is asked how he could possibly be so strong. Admitting the truth as to why they're at the museum, Bob opens up about his genetically modified scheme. Having the thighs of a grasshopper and the sonar of a killer whale, Bob came to the museum to harvest DNA from the smartest minds around. Bart comes to Lisa's rescue, but Bob warns he can be very easily driven into a murderous rage...which of course he is quickly driven to. As so often works, Bart and Lisa beg Bob to sing to them before he kills them, and after some Walt Whitman quotes from Lisa, Bob realizes he's a monster. He attempts suicide in the lake, but recalls that he has gills...defeated once again.

1 He's Grown Accustomed To His Face

In an interesting turn of events, someone attempts to kill Homer, not Bart. Having no clue who is attempting to take Homer's life, the Simpsons turn to Wiggum for help. They decide that hiring a murderer would help to understand how a murderer thinks, and so they take on Sideshow Bob to help solve the case and discover who Homer's would-be killer is. Bart is understandably uncomfortable by all of this, but is given a remote for a shock bracelet that is taped to Bob's leg hair. Eventually it is sorted out that Frank Grimes Jr. is responsible for the attempted murder, believing that Homer drove his father insane...which is true. All solved, getting things back to normal, Bob hides behind Bart's door, and waits for everyone to go to sleep before exacting his revenge at long last. Bart reaches for the remote, but Bob already has it in hand and, taping Bart's mouth shut, Bob pulls his knife. However, because of all the two have been through over the years, Bob cannot kill Bart. A la My Fair Lady, Bob's grown accustomed to his face.


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The 15 Most Heinous Acts Committed By The Simpsons' Sideshow Bob