Sideshow Bob (Terwilliger) has been sent to jail six times. Now for your reading pleasure, a description and summary of each major episode he has been in, including some modus operandi pictures, or things that have helped Bob pull of his schemes:

KRUSTY GETS BUSTED

CASE NUMBER: 7G12
PLAN:

This is Sideshow Bob's first case. His plan is to frame Krusty the Clown and take over his show because he hates being the center of all his jokes and being mistreated. 

THE DOINGS A-HAPPENING:

Sideshow Bob began as Krusty the Clown's sidekick. Bart Simpson has always been a great fan of Krusty the Clown. One day "Krusty" showed up at the Kwick-E-Mart, read some magazines, had a burrito, got his foot stepped on and oh ya, robbed The Kwick-E-Mart's owner, Apu, at gun point. "Krusty" got away with it. Krusty the Clown was at home when a SWAT team broke down his door and dragged him to jail. Sideshow Bob then took over and renamed Krusty's show to Sideshow Bob's Cavalcade of Wisdom. On which, he read novels to children. Meanwhile, Krusty the Clown had been put on trial for the armed robbery of the Kwick-E-Mart. Bart was there at that trial. He watched Krusty's little feet go into the trial as Krusty admitted he could read, he watched the surveillance tape of "Krusty" robbing it and he still couldn't believe that he had done it. Later, Bart went on S.C.of W. Bob noticed that he was looking sad, so he invited Bart up on stage to try to cheer him up. As Bob was speaking Bart was going over the evidence and the video tape. And when Bob said "...big shoes to fill..." he realized that "Krusty" in the video was not Krusty the Clown. He accused Sideshow Bob and then stepped on his foot. Bart then explained to the police thast Krusty couldn't read, had small feet and had a pace-maker. He explained that "Krusty" a.k.a. Sideshow Bob in the video, read a magazine, got his big foot stepped on and ate a microwave burrito. 

FOILED BY:
VERDICT:
RESULT:
Bart Simpson
Convicted of Framing Krusty and Armed Robbery
His first of many visits to jail 

THE BLACK WIDOWER

CASE NUMBER: 8F20
PLAN:

Bob plans to marry his prison pen pal, Selma, to get her money and to get revenge at Bart. 

THE DOINGS A-HAPPENING:

Selma has been having this relationship with this prisoner, 1211, through a prison pen pal program. The prisoner is released and comes to dinner with the Simpsons and Selma and Patty. That prisoner is Sideshow Bob! Bart and Lisa are terrified. However, Sideshow Bob acts very nice to everyone, and then asks the question to Selma, "Will you marry me?". She says yes and Bart is very worried. Selma reveals that she has no sense of smell, when the wedding menu is being made. Also, Sideshow Bob agrees to go on a walk when ever McGuiver is on. Bob and Selma go off to a Shelbyville hotel to celebrate their honeymoon. The Simpsons soon receive a video tape of the honeymoon just getting started. Bart notices that Sideshow Bob was making a big deal about a fire place. When Bart is watching television he realized that Sideshow Bob is going to kill Selma. Meanwhile, Bob turns on the gas in the hotel room and leaves when McGuiver starts. He knows that her one cigarette will ignite the whole place, and that her lack of smell will make her unaware of the gas. Bart tries several ways to explain this to Homer, but he doesn't get it. One try and Marge understands completely. The apartment explodes and when Sideshow Bob enters, he is confronted by Bart. 

FOILED BY:
VERDICT:
RESULT:
Bart Simpson, with help from wedding video
Convicted of Attempted Murder
Wiggum blows place up via match from cigar, Bob in jail 

CAPE FEARE

CASE NUMBER: 9F22
PLAN:

Sideshow Bob set his sights on Bart in this Episode. From his prison cell, Sideshow Bob had been writing numerous death threats to Bart. His plan was to keep terrorizing him and then, escape and kill Bart. 

THE DOINGS A-HAPPENING:

After receiving many death letters, written in blood, Bart Simpson was worried. Bob was put up for parole. When asked about the tattoo "Die Bart Die", he explained that it simply was German for "The Bart The". After charming the review board, he was granted parole and released. The first encounter the Simpsons had with Sideshow Bob was at a movie theater. Sideshow Bob was sitting in front of the Simpsons, smoking a cigar and laughing. Homer confronted him and realized who it was. Bart immediately went into shock, and Marge told Bob to stay away forever. Because of this encounter, the Simpsons were placed into the Witness Protection Program. They were renamed the Thompsons and moved to Cape Feare. Sideshow Bob hid under their car while they were moving. After Homer drove through a stretch of desert with lots of cactus and reached their new home, a riverboat, Sideshow Bob got out from under their car. In a ridiculously long scene, he kept stepping on rakes. This scene was this long because they need to fill up some time. Bart tried to go on with his life, but after seeing Sideshow Bob many times, he was very worried. Homer did nothing to help either. He burst into Bart's room to show him his new hockey mask and chainsaw and to cut him some warm brownies. Once this was over, Sideshow Bob cut the rope on the riverboat so it started to drift. He confronted Bart and cornered him. Bart, for his last request, asked Bob to sing him all of "H.M.S Pinafore". Bob did and by the time he was done, the boat had drifted to Springfield, where the cops where waiting. 

FOILED BY:
VERDICT:
RESULT:
Bart Simpson, and the current of the river
Convicted of Guilt
Bart ordering the police around, and Bob in jail 

SIDESHOW BOB ROBERTS

CASE NUMBER: 2F02
PLAN:

His plan this time was to get out of prison and run for mayor. Once he had won, he was going to force the Simpsons to move, and destroy their house.

THE DOINGS A-HAPPENING:

Lisa had to listen to Birch Barlow for school. When Bob called into Birch Barlow's show, Lisa and Homer were relaxed. Bob explained his position and Birch Barlow said that he was a prisoner of the system. He also said that he must be released! Lisa brought a radio into Bart's room and told him is mortal enemy was on the radio. Most of the town heard Birch Barlow's plea for Bob's release, and a group of supporters, rallied behind him and went to the Mayor's office to protest. By order of the Mayor, Bob is released from the island prison. After he has fallen off the island, he is informed that the boat is on the other side. Bob then decides to run for mayor. With the support of Birch Barlow and the rest of the republican party, Bob runs for mayor. He and Quimby go to the school as part of their campaigns. Bart is confronted by Bob. Bob puts on a little show in front of the kids to make them like him. Bart and Lisa realize this and go hug Mayor Quimby. Bob snatches Bart into his limo and puts vote Bob pins on him. Another stop on the campaign route is a televised debate on FOX. Mayor Quimby has the flu and Bart has been feeding him, by accident, extra drowsy medicine. The debate goes great for Bob. Bob ends up winning as mayor. The construction of the new Matlock Expressway is blocked by the Simpsons house. Bob tells the Simpsons that if they do not move they will tear down their house. Bart and Lisa know Bob didn't win fairly, but they don't have evidence. With the help of Waylon Smithers, they are told to follow the names that they have been researching. As it turns out, all of the dead people in Springfield voted for Bob, including, Snowball I, their dead cat. Just as the Simpson house is about to be torn down, Lisa and Bart confront Bob. They take him to court and trick him into admitting his guilt.

FOILED BY:
VERDICT:
RESULT:
Bart and Lisa Simpson, with Smithers help
Convicted of Election Fraud
Participates in the prison's crew race against Yale in Springfield Minimum Security 

SIDESHOW BOB'S LAST GLEAMING

CASE NUMBER: 3F08
PLAN:

This time, Sideshow Bob held the entire town of Springfield ransom, his demand - to get rid of television. After escaping from a prison work session at the airbase, Sideshow Bob stole an H-bomb and ransomed the Airshow, along with Springfield. 

THE DOINGS A-HAPPENING:

Because of the laughter of his cell mates, Bob ruined his model of Westminster Abby in a bottle. Outraged, he went into a speech about how horrible television was. When he and other prisoners were taken to the Springfield air base to clean for the upcoming air show, his anger was fueled even more when his huge pile of condom wrappers were blown away by an jet passing over him. Later that night, his hatred for television grew when a star he knew was reduced to being on a sitcom. The next day when he was back at the air base, he was told to "get busy" by Chief Wiggum. Bob replied, "Oh I'll get busy, very busy indeed. Bwahahaha...", indicating that he was up to no good. He sneaked away and commandeered a General's private washroom. Imitating the verbal scolding that he received, he got access to a hanger with bombs in it. He then took one and set up base in the Duff Beer Blimp, which was stationed on the ground. The air show had begun, when Bob seized control of Trivano Vision and announced that they must abolish television in two hours, and, oh ya, he had a bomb. The Simpsons family, who were at the airshow, panicked. Bart stayed behind because he wanted to see all the action, Lisa stayed to try to get Bart. Anyways, a committee is formed to find Bob, but they can't. So television is demolished. Sideshow Bob wins? No. Krusty the Clown has gone to the Alkily Flats to broadcast from the emergency channel. Bob, in anguish, is about to blow the bomb. Lisa, figures that he is in the Blimp because of his high voice. Bart and Lisa, burst into the blimp and try to stop Bob, no avail. He detonates the bomb. It is, however, a dud. Bob grabs Bart and is about to kill him when he hears the police surround the blimp, Lisa has sent a message to the police using the display board. While all this has been happening, Marge and Homer have been trying to get back into the air show. Bob cuts through the blimp and takes him and Bart into a Harrier Jet. He can't take off, so he high-jacks the Wright Brothers' plane. He is followed, slowly, by Homer, Marge and Lisa in their car, and the population of the air base - walking. He heads towards the shack where Krusty is broadcasting, planning to kill him. Bart tries to talk him out of it, but he crashes into the shack at full speed. Nothing happens. He and Bart fall out of the plane, Krusty is safe and the Air Force and police arrive. 

FOILED BY:
VERDICT:
RESULT:
Bart and Lisa Simpson
Convicted of Guilt
Wright Brother's Plane crushed by tank and Bob in jail 

THE BROTHER FROM ANOTHER SERIES

CASE NUMBER: 4F14
PLAN:

This time the plan came from the evil, new, mastermind, Cecil, Sideshow Bob's brother. He embezzled money for concrete from the Springfield Dam construction project to keep to himself. After which, he would blow up the dam to cover-up any evidence. Everyone in the town would think it was Sideshow Bob. Cecil wanted to frame Bob because he wanted the money and Bob stole the role of Krusty's Sidekick, from Cecil, many years ago. It was a good coincident that Sideshow Bob, Bart, and Lisa ended up in the Dam after finding out Cecil's plan, that meant he could eliminate them too. 

THE DOINGS A-HAPPENING:

Sideshow Bob, now truly reformed, was released from prison, by Reverend Lovejoy, via the Worker's Release program. Sideshow Bob thought no one who hire a 5 time loser like him, but someone did, his Brother. When Bart heard the news of Bob's release, he immediately when to the jail, along with other protesters. However, Sideshow Bob was released. Things started off well, Bob went to work for (not with) his brother at the construction of the Springfield Dam, as Construction Supervisor. He was however, agitated, by some of the lower class workers, that he had to deal with. Meanwhile, Bart had convinced Lisa to help him search for evidence that proved Sideshow Bob was up to no good. Doing so, he rummaged through Bob's trash, spied on him in many locations, which, in turn, ruined Bob's only chance with Edna Krabapple. Sideshow Bob became very annoyed by this. Finally, Bart and Lisa found something. Over a million dollars, cash, was in a briefcase in Bob's office. Further investigating, by Lisa, found that large supplies of concrete had been embezzled. When Bob went to his office, the children lead him on a chase through the dam. That ended in a room where the children confronted Bob, and he realized Cecil was in charge of the concrete. Cecil showed up and locked them in the room after revealing his plan to blow up the dam "One minute to sunrise". Bob lead the children down a water pipe and to freedom. Bob and Lisa were about to defuse the bomb when Bart was thrown off the edge by Cecil, whom Bart tried to surprise. Cecil lost his gun and the money while Bob, without second thoughts, leapt off the dam and rescued Bart. When the police arrived, Chief Wiggum would not listen to both Bart's and Lisa's testimony that Bob was innocent.

FOILED BY:
VERDICT:
RESULT:
Bart and Lisa Simpson, and Sideshow Bob
Wrongly Convicted of Guilt
Fighting over top bunk in jail, with Cecil