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The Simpsons is not a show that’s big on continuity. One of its many characters might change in one episode and then immediately revert by the next. One piece of continuity that remains, though, is that Bart Simpson proved Sideshow Bob for framing Krusty for robbery, and now Sideshow Bob wants to kill him. And he’s tried. A lot. Probably the show’s most beloved (and one of my favorite) recurring guest stars, Sideshow Bob episodes are almost always the highlight of a season. I'll actually tune in whenever I get the word that he's showing up in this day and age of the Simpsons.
Here's all of his episode where he is featured as a main character.
"Krusty Gets Busted": Sideshow Bob's villainous debut. His hair has changed from an afro to a palm tree fronds hairdo. Krusty the Clown is framed for robbing the Kwik-E-Mart, and the entire town abandons him and embraces his replacement, the suave, sophisticated Sideshow Bob. However, Bart never loses hope in Krusty and is eventually able to unmask the identity of the real culprit... Sideshow Bob.
"Black Widower": Selma begins dating her prison pen pal, who the Simpsons discover is none other than Sideshow Bob. Sideshow Bob declares that he has been reformed by Selma's love, and eventually proposes to and marries her (all to the objection of Bart, who still believes Sideshow Bob is pure evil). On their honeymoon, it is revealed that Sideshow Bob only wants to kill Selma for her insurance money, but Bart manages to unravel his scheme and stop it at the last second, sending Sideshow Bob back to prison.
"Cape Feare": Bart receives a series of threatening letters written in blood, and soon afterwards Sideshow Bob is released from prison on parole. Discovering that he is responsible for the threats and is planning to kill Bart, the Simpsons go into the witness protection program and move to Terror Lake, but Sideshow Bob follows them. After a few days of stalking, Sideshow Bob finally sneaks into the Simpson's new home to kill Bart. The two end up confronting each other on the deck of their small boathouse, but Bart manages to outwit Sideshow Bob by asking him to sing the entire score to the H.M.S. Pinafore as a last request. This delays Sideshow Bob long enough for the boat to crash, where a waiting Chief Wiggum arrests him (telling Bob "It's a good thing you drifted by this brothel"). This episode also features the first scene with Bob's slapstick act of accidentally stepping on numerous rakes, which hit him in the face. This episode is largely a spoof of the 1991 film version of Cape Fear.
"Sideshow Bob Roberts": Sideshow Bob's outspoken and eloquent conservative viewpoints cause the town Republicans to parole him and get him to run for Mayor against Quimby, where he wins in a landslide (one of the arguments against Quimby being that he agreed to parole known criminal Sideshow Bob). Sideshow Bob uses his new power to make the Simpson family suffer, scheduling their home for demolition and putting Bart in Kindergarten (though this actually makes Bart happier). Lisa discovers that Sideshow Bob won the election by registering dead people to vote for him. Lisa and Bart confront Sideshow Bob with the truth, and Sideshow Bob is arrested and sent back to jail.
"Sideshow Bob's Last Gleaming": Sideshow Bob's hatred of television prompts him to steal an atomic bomb from the Springfield Air Base, and he threatens to destroy all life in Springfield unless television is permanently cancelled. Krusty violates the cancellation, so Sideshow Bob attempts to detonate the bomb, but it turns out to be a dud ("best before November 1959"). Sideshow Bob then takes Bart as a hostage and goes off on a kamikaze mission aboard the Wright Brothers' plane to kill Krusty, but is foiled by the frailty of the Wright flyer.
"Brother from Another Series": Sideshow Bob is released from prison and enters into a work-release program headed by his brother Cecil played by David Hyde Pierce Grammer's co-star and fictional brother from the television series Frasier. The program is a construction project working on the new Springfield Dam. Bart and Lisa believe Sideshow Bob is planning something terrible, and spy on his every move. The two run across evidence that suggests Sideshow Bob is planning to wipe out Springfield by sabotaging the dam. Eventually, it is revealed that Sideshow Bob really has reformed, and that it is his brother Cecil that is planning on destroying Springfield to frame Bob as revenge for 'stealing' the position of Krusty's sidekick from him (but mostly for the money he made from using cheap materials for the dam). Bart, Lisa, and Sideshow Bob team up to stop Cecil's plan, and Bart even saves Sideshow Bob's life when the dam begins to collapse. Moved, Sideshow Bob promises to stop trying to kill him. However, Sideshow Bob ends up taking an equal share of the blame for Cecil's scheme, and both of them are hauled off to jail by Wiggum.
"Day of the Jackanapes": Krusty the Clown becomes sick of annoying network executives, prompting him to arrange for a final episode. Meanwhile, Sideshow Bob is enraged when he learns that Krusty has destroyed all evidence of his existence by taping over his old episodes (since Krusty had a love for Judge Judy and didn't want to buy blank tapes), prompting him to enact yet another "kill Krusty" scheme, this time by hypnotizing Bart into becoming a suicide bomber and killing Krusty on the show. During the initial hypnosis, he continues with his 'Walk into a rake and shudder' act, proclaiming the rake to be his greatest arch-enemy in his life beyond Bart. However, at the last minute, Krusty makes an on-air apology to Sideshow Bob for all the pain he's caused him, causing Sideshow Bob to have a change of heart. Sideshow Bob warns everybody that Bart has a bomb, prompting Krusty's pet monkey, Mr. Teeny, to swoop in and throw the bomb away (the only people hurt are the network executives, whose body parts merge into a T-1000-like monster). Sideshow Bob and Krusty finally resolve their differences, but Sideshow Bob is still scheduled to be decapitated for his crimes by Chief Wiggum (although the show cuts to the credits before we see the impact). He must have survived somehow, though, because he next appears in:
"The Great Louse Detective": A series of attempts on Homer's life prompts Chief Wiggum to consult Sideshow Bob as a Hannibal Lecter-style expert on the criminal mind. Sideshow Bob is eventually sent to live with the Simpsons to help reveal the killer's identity, with an electric shock device strapped to him to prevent him from causing trouble. In a final confrontation at Mardi Gras, Sideshow Bob saves Homer's life and the two confront the real killer: Frank Grimes Jr. In the end, Sideshow Bob sneaks into Bart's room and is about to kill him, but finds that he can't do it because he's "grown accustomed to Bart's face" a la My Fair Lady. He later escapes, but not before receiving a number of electric shocks from the misplaced controller of his electronic bracelet.
"The Italian Bob": When the Simpsons visit a small Italian village, they find that Sideshow Bob is the mayor. His new wife and son - Francesca and Gino - know nothing about his murderous life in America, although Gino says "Die, Bart!" several times (apparently Bob is known to yell it in his sleep). Bob begs the Simpsons not to tell anyone. They trust that he has changed, and they agree. However, when Lisa gets drunk at a party, she reveals everything. All three Terwilligers end up vowing revenge (or "vendetta") on the Simpsons, apparently renewing Bob's murderous wishes. The Simpsons are nearly killed in the Colosseum, but Krusty saves them at the last minute. In this episode, it was implied that Bob experimented with homosexuality while in college. This episode may or may not draw inspiration from The Mayor of Casterbridge, in which a Mayor has similar familial secrets.
"Funeral for a Fiend" Bob and the entire entire Terwilliger family return along with Bob's father, Robert, and mother, Dame Judith Underdunk, making their first appearances. Bob fakes his own death and locks Bart in the coffin, which he attempts to cremate at the otherwise empty funeral home as all the Terwilligers laugh maniacally. They are foiled by Lisa and the rest of the Simpson family and sent to prison. This episode is also notable for guest starring John Mahoney makes his first appearance as Dr. Robert Terwilliger, Sr., the father of Bob and Cecil.
Bob reappears again in the episode "The Bob Next Door" where he switches faces with his prison cellmate Walt Warren. Bob returns to Springfield and moves into the house next to the Simpson family, assuming Walt's identity. He exploits this to make his latest attempt to kill Bart legally over state lines, but is foiled again and gets taken away by state police.
In "The Man Who Grew Too Much" Bob was revealed as a Chief Scientist for a genetic engineering company named Monsarno, having received the position after he was selected as a test subject and published the results of the experiments to which he was subjected. He and Lisa bond over their interest in Walt Whitman, but Bob soon reveals that he has also genetically modified himself to give himself various superhuman abilities, intending to acquire DNA from the relics of various historical figures stored in the Springfield Museum to make himself a superhuman dictator. However, after he is provoked into a fight, he realizes that he has become a crude monster and jumps off the Springfield Dam, surviving because the gills he gave himself allow him to survive in the lake.
During Treehouse of Horror XXVI segment "Wanted: Dead, then Alive", Bob successfully kills Bart, but finds his life so meaningless in Bart's absence that he creates a machine to bring Bart back to life so that he can keep killing his enemy over and over, until the other Simpsons rescue Bart and Bart turns him into a twisted amalgamation of creatures.
He's also made brief cameos in a few other episodes, but I did not count them. Anyway, what is your favorite Sideshow Bob episode? I know a lot of people will say Cape Feare, and rightfully so, but mine is actually between Brother From Another Series and Sideshow Bob Roberts.