Sideshow Bob's been sent to jail 7 times since he lost his role as Krusty's sidekick. He especially has a grudge against the 10-year-old Simpson boy, Bart, who sent him to prison the first time. Since then, whether getting revenge on Bart by murder or even through his family, or lunging back at Krusty for humiliating him all those years ago, he's always up to something as Springfield's #1 villain.

Let's take a look at his record, shall we?

case 1 (first ever): Krusty Gets Busted [7G12]
No one is sadder than Bart Simpson when his TV hero Krusty the Clown is arrested for a convienience-store robbery. While Homer must testify against the clown after witnessing the robbery, Bart refuses to believe it as the truth, and for good reason as we find out later when Krusty is unfairly arrested when Homer identifies him. Springfield is in shock, as well as Krusty's 'faithful' sidekick, Sideshow Bob, who believes he must pick up where Krusty left off... by taking over the entire show himself, reforming it as "Sideshow Bob's Cavalcade of Whimsy". Bart and Lisa find this fishy and work together to prove Krusty's innocence. And that they do, upon later realizing some facts. Krusty is illiterate and has a pacemaker, Sideshow Bob does not. The details of the Kwik-E-Mart robbery don't agree with these characteristics of Krusty. It doesn't end there.

When Bart and Lisa attend a live taping of the new Sideshow Bob show, Bart accuses Bob on the air of committing the robbery, pointing out the facts mentioned as well as an important one that both the robber and Sideshow Bob have "big shoes to fill" (quote Bob), meaning they have the same oversized feet fit for Krusty's oversized clown shoes (Bart proves this by injuring Bob's feet on the air!). Bob confesses to the crime, admitting that he did it to frame Krusty out of revenge for Krusty's treatment toward him on the show: being the center of his cruel (and oftentimes painful) slapstick jokes, and overall, humiliation. Krusty is let go, and as he thanks Bart for his help in proving the clown's innocence, the "other clown" Sideshow Bob is sent right to jail with a hatred for the Simpson boy that will last for years...

Well done, you twisted little thang XD you're well on your way to being a Springfield celebrity already.
arrested for: framing of armed robbery.

case 2: Black Widower [8F20]
Selma Bouvier, aunt of Bart Simpson and a life-long man-hunter, has finally landed herself a boy. She's happier than ever, not acknowledging the dangers of her new love being a prisoner (being she met him via a Prison PenPal program), as well as who he is revealed to be when she invites him over for dinner to meet her family. Oh dear! Her boyfriend is Sideshow Bob! Bart is terrified to learn this and tells his aunt not to trust him. But much to his disgust and fear, Selma accepts when Bob proposes to marry her. Throughout the wedding, Bart is still revolted and his skepticism grows, especially while watching the honeymoon tape that Selma had made and sent to his family. In the tape, Bart discovers some things that just aren't right about Bob's behavior during the honeymoon. With careful observation, he concludes a theory. Quickly, he tells the family; and the family and the police make it to the hotel to save Selma before any dangers happen, and in this case, the hotel blowing up. Bart made it into the room to warn Selma seconds before she set the hotel to danger of an explosion.

Bart explains to everyone how he foiled Bob's plot, and learned his motive. Bob knew Selma was related to Bart (he having a grudge against the boy, of course), as well as the fact that Selma was doing very well financially ("Relax. I told you, I got money.") and a crucial thing: Selma had lost her sense of smell as a child, and smokes every time she watches her favorite sitcom, "MacGyver". This explains the reason Bob was so worked up over the gas fireplace in the hotel room, Bart figured - Bob was going to start a gas leak that Selma could not possibly notice and would cause the room to explode when she lit her cigarette, she would die and he would be left with her life savings. Even so, the hotel did blow up because the police, ultimately Chief Wiggum, had lit cigars to (ironically) celebrate Sideshow Bob's arrest.

Strike two. and there goes any last lingering thread of non-hostility he had for Bart...
arrested for: attempted murder.

case 3: Cape Feare [9F22]
"You're going to die Bart", "I will kill you, Bart" "See you soon Bart"... someone has been mailing Bart threatening letters written in blood. He's terrified to learn that it's Sideshow Bob, who vows revenge on him for sending him to jail. Even worse, Bob is able to come across as sweet and innocent to the jury, granting him a quick parole and freedom to wreak havoc on Springfield (specifically Bart). The family have no choice but to relocate to a new home. But does that stop Bob?

Of course not. On the ride to Terror Lake, he straps himself beneath their car ("Who wants to ride through the cactus patch, kids?!"). That night, the new houseboat dwelling of the Simpsons is broken into by the fiendish criminal, who ties Homer, Marge, Lisa, Maggie and even the family pets up and cuts the boat off from the dock, setting it adrift down the river. He reaches Bart, and before Bart gave himself up for lost, he stalls Bob by asking him to sing the entire score from the "H.M.S. Pinafore". Bob proceeds to do so, even Bart gets in on the act - neither one realizing they're close to Springfield, where they soon finish the performance - and arrive 'home', the police taking Bob back into custody right away.

Oooh. this was a close one, boy! Bob must really hate you now... anchors away!
arrested for: attempted murder.

case 4: Sideshow Bob Roberts [2F02]
It's Lisa's turn to spot Sideshow Bob this time as she decides to study the upcoming election, specifically Mayor Quimby's re-election bid for a school project. As she and Bart listen to a radio show hosted by an ultra-conservative politician, Birch Barlow, Lisa identifies the voice of Bart's arch-enemy. No, not Dr. Demento! Sideshow Bob, who is one of the callers on the radio show who tells Barlow about his 'cruel punishment'. And you may imagine Bart's horror when Bob has successfully manipulated Barlow, the media and even Mayor Quimby (under public pressure) into letting him free once more!

Soon, Bob is chosen as the leading Republican challenger in Mayor Quimby's election. When Quimby shows up disheveled and drowsy at a televised debate, the tables turn against him and Bob is quickly voted into office in what appears to be a landslide. With his new power, Bob announces plans to build a new Mattlock Freeway. Seems innocent enough? He warns the Simpsons they will be evicted from their home, for he must demolish their house for freeway construction. Bart is also knocked down to kindergarten in school. Lisa, meanwhile, is almost absolutely convinced the election was rigged and on her search for evidence (with Smithers' help), discovers the huge majority of people that voted for Bob are deceased. In court, Bart and Lisa con Bob into admitting that he was fully responsible for rigging the election. He is arrested and sent to a minimum security prison.

Musn't mess with the Mayor, Bob! That's what you get for getting dead people to vote for you!
arrested for: election fraud.

case 5: Sideshow Bob's Last Gleaming [3F08]
Don't you just *hate* it when you're building a tiny model of Westminster Abbey inside a bottle, and the laughter of your prison mates cackling at the television interrupts? Sideshow Bob certainly does. In prison, he starts sulking about the negative effects of TV on society. And this is why while doing work detail at a local air force base, he sneaks off and hides out in a hangar that stores nuclear materials... bad time for the Simpsons to go see the air show that's being featured there. Bob interrupts the show by appearing on TV and declares that he has a nuclear bomb and will detonate the entire town unless they abolish all of television. Mayor Quimby has no choice but to follow his orders and shuts down all TV operations (except Krusty, who sneaks broadcasting from an abandoned defense shack in the desert).

Bart and Lisa find out where Bob is hiding, but Bob manages to kidnap Bart and hop aboard an antique Wright Brothers plane from the show and to the desert, for as Bob tells Bart he knows about Krusty's loophole and is going to kill him! When they get there, the plane is too slow and weak and fails to wreck the 'studio'. While Grandpa Simpson says he's going to 'haul ass to Lollapalooza', Bob is caught by the Simpson family and the police force and thrown back into prison.

TV is a powerful thing, Bob. You'll have to suffer hearing the 'FOX' theme over and over and over...
arrested for: guilt, and illegally dealing with a nuclear weapon

case 6: Brother From Another Series [4F14]
For once, Sideshow Bob is actually trying to reform. Don't believe it? You should. He is let out of prison and is re-united with his brother, Cecil (played by David Hyde Pierce, "Frasier's" brother too. Aha!), who hires him a job of helping build a hydroelectric dam in Springfield.

Thing is, Bart is convinced Bob is still evil and is simply out to kill him again. He, with Lisa's help and teamwork, sneak around the dam to see what the (semi) evil one is up to. They find a briefcase of money, 'til Bob catches them but claims himself innocent and tries to explain it. Of course neither Lisa nor Bart believe him, until Cecil who - out of an act of resentment for his older brother when, years ago, Bob got chosen over Cecil to be Krusty's sidekick and shattered Cecil's dreams - reveals he's going to blow up the dam with Bob, Bart and Lisa inside, take the money and let Bob be blamed for the accident. The three manage to escape, however, and foil Cecil's plans. The police soon show, and Chief Wiggum refuses to believe Bob had no part in the incident. Mmhmm, you guessed it. Bob is arrested once more, but this time little brother joins him, at least for now...

His brother is certainly something else, But we know this for sure about Sideshow Bob: once evil, always evil!
arrested for: framed conviction of guilt.

case 7: Day of the Jackanapes [CABF10]
After years of his show, Krusty decides to quit show business... for good. During his last press interview with Kent Brockman, he says that he's erased and taped over all old episodes of the first 10 years of his show, specifically the shows with Sideshow Bob! And the ex-sidekick himself in prison hears this, catching it on TV (?!), and is indeed planning revenge on Krusty for disposing of his classic shows. Sideshow Bob is released from prison once again and attempts to start over by applying for a job at Springfield Elementary (though Bart isn't exactly as fearful this time), so that he could have Bart help him with his plan to murder Krusty on his final show.

Bob later hypnotizes Bart, commanding him to kill Krusty. And on that night of Krusty's show, Bob tapes a belt of plastic explosives to Bart's chest and tells him to get on stage and embrace the clown, so the explosives will explode and kill him. But see... as it turns out on the show, Krusty does a special tribute to Bob, as an apology for leading him into a life of crime. Bob is touched and takes back his vow of revenge, though he can't stop Bart. Before Bart can strike Krusty, Krusty's sidekick monkey Mr. Teeny sees the armed-belt and tosses it backstage, saving Krusty and the boy (yet killing a couple of network executives). Later, Bob settles things with Krusty and is forgiven, but at the end, Bob is informed he's received the death penalty. Not that that will stop him, of course. He's an evil genius, remember?

Tsk, Bob. The least of your crimes and you get this? You'll get out of it, we know.
arrested for: attempted murder.

case 8: The Great Louse Detective [EABF01]
Bart is not the only common murder target in the Simpson family. A mysterious person is out to get Homer Jay, and naturally, the family seeks help from the police. Chief Wiggum advises that in order to find a murderer, you must first seek someone who understands a homicidal mind. And this someone is none other than Sideshow Bob. He ends up moving into the Simpsons' home for round-the-clock guarding of Homer. (There's a but: Bob is still considered twisted, thus he has a shock device attached to his leg, with a remote zap-controller that everyone in the Simpson family can enjoy!)

Over much of following Homer from place to place in his everyday life -- from the Kwik-E-Mart to Moe's to even getting Homer's car smashed and having to get that taken care of by a mechanic, even -- all seems normal to Bob and the rest. Then things get a bit fishy. You see, there's a festival going on at this time, and the family's victimized patriarch is elected as the King of Mardi Gras. During the parade, all seems well, until, upon noticing several clues around, the gears turn in Bob's head and he and Homer go to search out the murderer. Eventually, our villain-other-than-Bob is found (identity of murderer undisclosed for non-spoiling purposes ;>), and all's well that ends well. Until Bob pops into Bart's room to have a last 'errand' to run: killing Bart right then and there. There's the crazed maniac we know! Alas, alas, Bob finds that in his heart of hearts, he can not kill Bart... for after all this time, he has become accustomed to the boy's face.

Gooood boy. You've done pretty well. Yet, you try so hard to be nice and civilized, but we know you all too well by now, hon...
arrested for: nothing at all. aside from a bit of Rhino-tranquilizing and buzzer shocks, he runs free this time.

case 9: The Italian Bob [HABF02]
It's another road trip for the Simpsons family today, as Mr. Burns has bought a new Italian sports car and needs Homer to fly to Italy and pick it up for him. The entire family arrives in Italy, grab the car, and decide to do some sight-seeing around the beautiful countryside. After being struck with a large Mortadella wheel, the car does not make it through the whole vacation and certainly does not arrive to Mr. Burns in good condition, either, and the family abandon it in Salsiccia, a small village in which they are stranded. The Simpson family meet an old peasant woman who does not speak a word of English, but fortunately, she tells them that the Mayor of Salsiccia speaks English. By some strange, completely unforeseen coincidence, the mayor happens to be Sideshow Bob.
How did he wind up there?! Sideshow Bob explains that after the last time he attempted to kill Bart, he decided to move to Italy to start fresh. He did very well for himself very quickly (only after rough times like attempting to correct a local woman's Italian, of course), once he was discovered to be excellent at crushing grapes with his large, large feet, as the Italian workers pointed out. He quickly went from wine-maker to Mayor of the village, and he reveals three bombshells that shock the family: One, that he no longer wants to kill Bart. Two, that he has taken a wife- a local Italian woman named Francesca. And three, that with Francesca, he has a very, very young son named Gino! Bombshell number four is how his new family have absolutely no knowledge of "Roberto's" criminal past, and he is their hero. In return for having Mr. Burns' wrecked sportscar fixed, the Simpsons promise, on Bob's begging request, to not tell anyone of Bob's past.
Unfortunately, this doesn't last long: Lisa, after sipping a little too much wine at a party Bob throws for the townspeople, blurts out that Bob is a cold-blooded, several-time attempted-murderer. Bob tries to lead Lisa away, pretending she's only rambling, but she trips, falls, accidentally rips off his formal mayor's suit and reveals the Springfield Penitentiary uniform he's wearing underneath. The entire town is shocked, angered, and completely remove Bob from his position as mayor. As the Simpsons take off in the good-as-new fixed car, Bob glares after them, humiliated, and swears a loud vendetta on them. (and this is how his son Gino learned one of his very first words: "Vendetta!")
Soon enough, the Simpson family discover Bob following them on a motorcycle. Homer attempts to steer his family to safety-- into a ditch, over ancient Roman ruins and buildings, and they end up stuck on top of Trajan's Column. Bob gives up on chasing them and is completely despondent, until his wife Francesca and son Gino find him and reassure him that revenge is a dish best served family style, and they will help him in his mission to kill the Simpson family.
Before the Simpsons try to find their way home, Lisa finds out that Krusty the Klown will be performing in Pagliacci at the Colosseum, and they go to find him for help. Krusty agrees to help them and puts the family in the show as extras. Sideshow Bob and his new family, however, quickly find them and corner them on stage, and Bob performs a moving rendition of Vesti la Giubba while Francesca and Gino attempt to finish off the Simpsons family members one by one. It's another failure for Bob, though, as Krusty's limo quickly pulls up and whisks the family away from him. Bob doesn't mind too much, though, as he walks off with his own little family and plots a whole new kind of revenge. . .

Ah, Roberto. Arrivaderci... for now...
arrested for: nothing at all. runs free again, with his own back-up this time...

case 10: Funeral for a Fiend [KABF01]
Homer Simpson and his son Bart are sent to the store to buy new batteries for their camera. Homer is a man who can never resist a good bargain, so he takes up an offer to get the batteries free... as a bonus to a $200 TiVo set. The family enjoy TiVo and use it to skip commercials when watching television, and all is well until Marge starts having nightmares of Keith Olbermann scolding Marge for not watching the commercials that pay for the TV she watches. Out of guilt, Marge watches every commercial that is on, including a rather peculiar one for "Wes Doobner's World Famous Family Style Rib Huts". The restuarant has just opened in town, so the Simpsons decide to check it out during its grand opening. When they arrive, however, they find the restaurant to be a dark, abandoned building. It turns out to be not-so-deserted, as someone dressed as a cowboy locks the door behind them. That someone is Wes Doobner-- or as we better know him, and as Lisa knows him by his voice, Sideshow Bob.
Bob enthusiastically tells the Simpsons how he plans to destroy them by having them die in an explosion triggered by an overheated notebook-computer battery: the computer will blow up and ignite a pile of TNT close by. During his bragging, he quotes Shakespeare, and Lisa informs him that he got the quote wrong. Our defensive Shakespeare buff insists he's right, but proceeds to use the computer to look up the correct phrase. Bob's plan almost goes well, but just almost; as the computer explodes in his hands. But of course, the rest backfires and soon enough, the police show up and arrest him. Later on, Bob goes to trial, and his family are there to testify for him: his mother, Dame Judith Underdunk (a world-reknowned Shakespearean actress), his father, Dr. Robert Terwilliger Sr., and his brother Cecil. His wife Francesca and son Gino are also present. Papa Terwilliger explains that Bob has a rare heart condition his whole life, and mentions that Bob's psychotic actions are solely Bart's fault. Everyone in court - including Bart's own father Homer - believe in Dr. Terwilliger and turn against the boy. Bart defends himself and says Bob is just playing the town for fools. Meanwhile, Sideshow Bob takes out a small vial of nitro-glycerin... but what for?! What if it's an explosive?! Bart panics and grabs the vial and throws it out the window to save everyone. Bob angrily reveals that this was his heart medicine and not an explosive, but before he can finish, he suddenly staggers and collapses onto the floor. Dr. Terwilliger pronounces his son dead on the spot. (!!)
The whole town shows up to Sideshow Bob's funeral, and believe it or not, everyone is grieving something terrible. Everyone, that is, except Bart, who declares he's glad Bob died and yet Bob still makes his life miserable even in death. After the service, Bart briefly speaks with Cecil, and he finally feels a pang of guilt. He decides to visit Bob at the Springfield Funeral Home and make peace with him once and for all. When he does, Bart gets the shock of his life when a very much alive Sideshow Bob jumps out of his coffin and attempts to switch places with Bart, so that Bart will be the one getting cremated and Bob will run away a free man. While Bart is trapped in the coffin and is on his way to being burned to death, Lisa, back at home, figures out that Bob faked his death with the help of his entire family, complete with a powerful drug that simulates death injected into him by his father (and that's how he "died" in court!). She quickly leads the family to the funeral parlor and they save Bart right in the nick of time, distracting Sideshow Bob by blinding him with the ashes of an unclaimed person.
Bob asks Lisa how she untangled his web this time. Simple: she mentions how she was very suspicious of Bob's coffin: it had extra room for his huge feet, which the family would not have even considered if Bob had really died. The entire Terwilliger family are then arrested by the police and thrown into jail, where Bob, in a straight-jacket instead of a new prison uniform, goes into a slight case of delirium; having dreams of leaping out of a "10th Foiled Plot" anniversary cake and killing the entire Simpson family as his family just play cards to pass the time they're doing (to be exact, 87 years).

Aww, your first family road trip... straight to prison. You've got your family behind you, don't give up, you crazy boy.
arrested for: feigning his death, attempted murder. (along with his father, mother, brother, son, and wife)

case 11: The Bob Next Door [MABF11]
There is a massive economic crisis in Springfield, and Mayor Quimby takes drastic measures in an attempt to fix it (instead of covering it up, as usual): schooldays at Springfield Elementary are cut to only the ride on the schoolbus, roadkill remains on the road (too expensive to clean that up?!), more and more houses go up for sale, and as a result, more people are moving around-- especially the excess prisoners at Springfield Penitentiary being moved out, those released convicted of only minor offenses. Thusly, Bart Simpson has nothing to worry about, for 10-time convicted attempted-murderer Sideshow Bob is not getting out anytime soon and the boy will be perfectly safe.
A mysterious man named Walt Warren moves into the house right next door to the Simpsons. Bart and his family meet him, and while Homer, Marge and Lisa seem enchanted, Bart finds something frighteningly familiar about Walt's voice: it sounds a lot like Sideshow Bob. So much so, infact, that Bart believes Walt is Sideshow Bob in disguise. He tries all sorts of things to discover Walt's true identity: by singing Gilbert & Sullivan, knowing Bob's fondness for it (though Walt politely declines, saying he enjoys country music instead), and by sneaking into Walt's house trying to find proof of Bob's identity -- until Marge stops him fast. Marge worries about Bart's paranoia, and she takes him to Springfield Penitentary to put his fears to rest in showing him that Sideshow Bob is still kept under lock and key as always. Marge is right: Bart sees that Bob IS indeed in his cell, in a straightjacket and a pen held in his teeth, writing death threats to Bart all over the walls. Bart returns home with his mother, worry-free.
Upon returning home, Bart runs into Walt, who asks the boy if he would accompany him to an Isotopes vs.Spokane Cascades baseball game. Bart accepts and they begin driving to the game in Walt's car. Bart notices something is off when Walt does not make the turn off the freeway to Springfield Stadium, and he mentions this to Walt. Walt finally turns to the boy with a familiar, evil grin, and tells him something's up all right: he is indeed Sideshow Bob, and he proves it by taking off his shoes and stretching out his familiar, ginormous feet to confirm Bart's suspicions! And at the same time, "Sideshow Bob" at Springfield Penitentiary makes his own hasty escape and goes to the Simpsons' house first thing. Of course, he is not welcomed warmly (Marge with a hose, Homer slamming a window shut on him), "Bob" -- actually the real Walt Warren -- pleads with them that he is not Sideshow Bob at all and that the criminal has stolen his identity. (And he shows his very small feet to prove that.) He takes the family to Bob's place of residence and shows all the pictures of Bart with knives in them, effigy Barts being hanged and drowned, and the most telling of all: a picture of The Five Corners, U.S.A., where five states meet and apparently where Bart Simpson will die; as noted from Bob's handwriting of "Kill Bart Here" scratched onto it. Walt and the Simpsons rush like crazy to Five Corners to save Bart.
Bob tells Bart his plan: his cellmate Walt was a minor offender in prison and had a similar build and facial structure as Bob, so the obvious solution was an (amateur) facial transplant surgery, performed by Bob himself right there in their cell. The surgery was remarkably a success, as Bob just walked out when the prisoners were released, posing as Walt Warren and even using his investments to buy the house next door to the Simpsons'. Bart is understandably horrified, but not nearly as horrified as the poor waitress Bob meets when he and Bart stop at a diner, who flirtatiously pulls what she thinks is a loose thread on his jacket collar but actually is one of the stitches from Bob's face transplant, and reveals... a very, very ugly, faceless criminal-turned-amateur-surgeon. Bob runs away and drives off again with Bart, closer and closer to Five Corners. The waitress proves somewhat helpful to the Simpsons and Walt when they stop at the diner and describe Sideshow Bob (as Walt) to her. She lies and says he was going to Mexico, and then tries the same flirtatious jacket-thread-pulling technique on Walt, but the results are similar as his face quite nearly comes off too. Walt believes the waitress is possibly attracted to and may be trying to protect Bob, so he does not follow the Simpsons to Mexico and goes to Five Corners instead...
...where Sideshow Bob is right now with Bart and describing how he will stand in one state, Bart will stand in another, and as the bullet is fired in such a way that it ricochets through two other states before it hits Bart. It is this through this method that Bob makes it so he can not legally be prosecuted in any state, Bart dies, and he's happy. This doesn't work so well as Bart doesn't cooperate, and Walt Warren arrives and immediately takes the gun from Bob. However, a bee finds its way under Walt's transplanted face and doesn't let him hold on to the gun long. Fortunately, the police from [state where Springfield is in here], including Chief Wiggum, arrive and it's the same old story: Bob is under arrest once again and taken away. Bart notes that he actually told the police of his suspicions about "Walt" before leaving for the Isotopes game with him. After a few attempts by Bob to jump into other states and out of Chief Wiggum's long, chunky arm of the law, but failing at any escape due to the presence of police from the four other states, he is taken away to be chucked right back into prison... just in time for Homer and the rest of Bart's family to come in, a bit belated due to Homer arguing over how to say taco "in Mexican" with a local.

So you can sing, dance, AND do amateur surgery! Not bad, not bad. What will you do next?
arrested for: attempted murder, identity theft.

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disclaimer: "The Simpsons", 'Sideshow Bob' and related characters Matt Groening and FOX. "Evil Laughter" is a part of, Janna Correa.