On The Simpsons
The character of Sideshow Bob began his career as the non-speaking sidekick on Krusty the Clown's television show. The episode "Brother from Another Series" (season eight, 1997) reveals that Bob only received the job after his younger brother Cecil failed an audition, because Krusty considered Bob to be a perfect comic foil. After repeated instances of abuse, including being shot from a cannon and hit constantly with pies, the Yale-educated Bob became angry at Krusty and resentful of the clown's success. In "Krusty Gets Busted" (season one, 1990) Bob frames Krusty for armed robbery of the Kwik-E-Mart. After Krusty is arrested, Bob takes control of the show, introducing children to elements of high culture. However, Bob's reign is short-lived; Bart Simpson exposes the plan, Krusty is released, and Bob is sent to jail.
In "Black Widower" (season three, 1992), Bob's first major appearance after framing Krusty, he is released from prison and marries Bart's aunt Selma Bouvier. As part of a scheme to inherit money she has invested in the stock market, Bob attempts to blow Selma up during their honeymoon. Bart again foils the plan and Sideshow Bob returns to prison. After being paroled from prison in "Cape Feare" (season five, 1993), Bob targets Bart directly, threatening him repeatedly and forcing the Simpsons into hiding as part of the Witness Relocation Program. Bob follows them to their hideout, a houseboat on Terror Lake, and, after subduing the family, prepares to kill Bart. He allows a final request, however, and Bart asks to hear Bob sing the entire score of H.M.S. Pinafore. The delaying tactic leads to Bob's third arrest.
Bob is released from prison once again in "Sideshow Bob Roberts" (season six, 1994), and runs for Mayor of Springfield as the Republican Party candidate. He defeats Democratic Party incumbent Joe Quimby in a landslide, but Bart and Lisa discover that Bob rigged the election, leading to another incarceration. Bob escapes from prison for the first time in "Sideshow Bob's Last Gleaming" (season seven, 1995), and threatens to blow up Springfield with a nuclear bomb unless the city stops broadcasting all television shows. He is thwarted when he finds out that the bomb itself is a dud, then kidnaps Bart and flies the Wright Brothers' plane in an attempt to kill himself, Bart, and Krusty (who is hiding inside a shack). This too is thwarted, and Bob returns to prison. In the following season, Bob takes advantage of the prison's work release program, and appears to be genuinely redeemed. In "Brother from Another Series," Reverend Lovejoy declares him a changed man and recommends him for a work release opportunity. Bob is discharged from prison into the care of his brother Cecil, who is Springfield's chief hydrological and hydrodynamical engineer. However, the scheming Cecil, still smarting over his failed audition for Krusty, tries to frame Bob by sabotaging the Springfield Dam. Bob, Bart, and Lisa together stop Cecil and save the town, and both brothers, despite Bob's genuine innocence, are sent to prison.
In "Day of the Jackanapes" (season 12, 2001), Bob discovers that Krusty has erased all of the early shows featuring Sideshow Bob as Krusty himself is declaring his fifth and final retirement after being annoyed with the network executives. Bob is released from prison and develops a plot to kill Krusty using Bart as a suicide bomber during Krusty's retirement special. Just as Bob was to succeed, he overhears Krusty publicly holding himself responsible for turning Bob into a criminal, expressing his regret of mistreating Bob during his years as Sideshow. To appease things, Krusty sings himself a song on Bob's behalf, and being touched by this, Bob decides to abort his plan of attempted murder and reconciles with Krusty, although he is returned to prison for it. Bob's aid is sought by Springfield police in "The Great Louse Detective" (season 14, 2002). After an attempt is made on Homer Simpson's life, Bob is released from prison to help find the culprit. When the mystery is solved, he returns to murder Bart. However, Bob finds he is "accustomed to face" and cannot do it.
It is revealed in "The Italian Bob" (season 17, 2005) that Bob has moved to Italy to make a fresh start. He is elected mayor of a village in Tuscany and marries a local woman named Francesca, with whom he has a son named Gino. The Simpson family, in Italy to retrieve a car for Mr. Burns, encounters him by chance. Bob welcomes them with hospitality on the condition that they not reveal his felonious past; however, a drunken Lisa jokes about Bob's criminal deeds, alienating Bob from his citizens. He, his wife and son swear a vendetta on the Simpsons. The entire Terwilliger family returns in "Funeral for a Fiend" (season 19, 2007) in which Bob's father, Robert, and mother, Dame Judith Underdunk, make 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. Bob briefly returns in the season 20 episode "Wedding for Disaster", when Bart and Lisa initially suspect Bob of kidnapping Homer to prevent him from attending his second wedding with Marge (due to a keychain they found had an 'S' and a 'B'), but Krusty provides him with an alibi, explaining to the kids that Bob was with him the whole day. Eventually, Bob and the kids discover the true culprits, Patty and Selma.
Bob re-appears again in the episode "The Bob Next Door" (season 21, 2010), 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. Bob briefly returns in "At Long Last Leave" (season 23, 2012), where he attends a town meeting to decide on if the Simpson family should be banished or not, and he expresses his desire for the former to happen.. He also appears briefly in "Moonshine River" (season 24, 2012), where he tries to sneak up from behind to kill Bart, only to be quickly hit by a train in the process.
Read more about this topic: Sideshow Bob, Appearances