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Bob never anticipated a career in show business. His younger brother Cecil (voiced by Grammer's Frasier co-star David Hyde Pierce) auditioned for the role of Krusty's sidekick, but Krusty thought Bob's uptight demeanour would make him a better comic foil, and gave him the job instead.
As the years went on, the highly-educated Bob became increasingly angered at being overshadowed by Krusty's "dilapidated vaudeville antics", not to mention Krusty's continual abuse. Finally, he snapped and framed Krusty for armed robbery. He took over the show, making it more upmarket (for example, Krusty's catchphrase "Children, who do you love?" was replaced by the grammatically correct "Whom do you love?") introducing culture, singing Cole Porter, and reading the classics to his rapt young audience. Although the show earned critical raves - and boffo ratings - his reign was shortlived, as Bart exposed his plan and landed him in jail.
Since then, he has taken the position of Evil Genius in the series - a typical Sideshow Bob episode involves his being released from incarceration and acting out some cunning plan, which is foiled by Bart and (usually) Lisa. Frequently this plan involves killing someone: Krusty, Bart or everyone in Springfield.
Bob was briefly married to Selma (whom he also tried to kill), and was the Robert Mitchum/ Robert de Niro character in the Cape Fear sendup episode. He is a Republican, and was briefly mayor of Springfield. He can sing entire Gilbert and SullivanPlaywright/lyricist William S. Gilbert ( 1836- 1911) and composer Arthur S. Sullivan ( 1842- 1900) defined operetta in Victorian England with a series of their internationally successful and timeless works. Their first major hit was HMS Pinafore ( 1878), operettas off the cuff.
Bob also has several tattoos, such as "Die Bart Die" ( GermanGerman (called Deutsch in German in which germanisch refers to prechristian times), is a member of the western group of Germanic languages and one of the world's major languages. It is the language with the most native speakers in the European Union., he claims, for "the Bart, the") on his chest and one resembling Bart's decapitated head on a skateboard on his back. The tattoos on Bob's fingers parody those of Robert Mitchum's character in the movie The Night of the HunterThe Night of the Hunter is a 1955 movie directed by Charles Laughton and starring Robert Mitchum, Shelley Winters, Lillian Gish, James Gleason, Evelyn Varden, Peter Graves, Don Beddoe, Billy Chapin, Sally Jane Bruce and Gloria Castillo. Night of the Hunte (whose fingers are tattooed L-O-V-E and H-A-T-E), but, as Simpsons characters have only four fingers, Bob's finger tattoos spell "L-U-V" and "H-Ā-T".
Bob's brother Cecil has harbored resentment for winning the role of Krusty's sidekick for many years, and during one of Bob's releases from prison, tried to frame him for embezzlement and sabotaging the Springfield Dam. Cecil's plan ended with mixed results: the sabotage did not destroy Springfield as expected, and both brothers took the blame for it.
Bob's position as Krusty's sidekick is now taken by Sideshow Mel.
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