Episodes in which he is a central character typically involve Sideshow Bob being released from prison and executing an elaborate revenge plan, usually foiled by Bart and Lisa.

A lover of Gilbert and Sullivan operettas, Sideshow Bob is also known for his singing voice; several of Grammer's performances have been included in The Simpsons musical compilations.

In the episode, he and Krusty plan a big event for whoever knows information of who captured the head of Jebediah Springfield's statue, and joins in on the town mob when it is discovered that Bart Simpson took it.

However, after repeated instances of abuse, including being shot from a cannon and hit constantly with pies, the Yale-educated Bob became angry with Krusty and resentful of the clown's success.

[12] In "Black Widower" (season 3, 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.

[13] After being paroled from prison in "Cape Feare" (season 5, 1993), Bob targets Bart directly, threatening him repeatedly and forcing the Simpsons into hiding as part of the Witness Relocation Program.

He defeats Democratic Party incumbent Joe Quimby in a landslide, but Bart and Lisa discover from Waylon Smithers that Bob rigged the election by using the names of deceased people.

Bob fakes his own death during his trial and locks Bart in the coffin, which he attempts to cremate at the otherwise empty funeral home as all the Terwilligers laugh maniacally.

[21] In "Sex, Pies and Idiot Scrapes" (season 20, 2008), Bob is one of the wanted criminals in Homer and Ned Flanders's bounty hunter job despite already being in prison, which he escapes from at the end of the episode.

After tempted into a murderous rage, he chases down Bart and Lisa and is about to kill them but however, he is provoked into a fight and he realizes that he has become a crude monster and jumps off the Springfield Dam.

In "Treehouse of Horror XXVI" (season 27, 2015), in the first segment called "Wanted: Dead, then Alive", Bob uses Milhouse's phone to trap Bart in the band classroom and successfully kills him.

Bob also appears in the episode "Gal of Constant Sorrow" (season 27, 2016), grunting in annoyance as he wipes off Bart's graffiti from Hettie Mae Boggs' promo poster on the wall along with Snake Jailbird and other inmates.

In the opening sequence, he is the self-appointed leader of a four-member group consisting of Homer's enemies, including Bob himself and the ghost of Frank Grimes.

Bob also makes a non-speaking cameo appearance in "The Nightmare After Krustmas" (season 28, 2016); he is amongst the crowd witnessing Krusty nearly drowning in a frozen lake while holding up a sign saying "Die Clown".

Several episodes later, in "Bobby, It's Cold Outside" (season 31, 2019), he is hired to play Santa Claus at a theme park, and later helps the Simpsons discover who is stealing everyone's Christmas gifts.

In the "Treehouse of Horror XXXIV" segment "Ei8ht" (season 35, 2023), in an alternative ending to "Cape Feare", Bob realizes that Bart is stalling his death by making him sing Pinafore, and as a result, kills him, traumatizing Lisa.

[29] In The Simpsons Game, released in November 2007, Bob has a speaking cameo appearance at the end of the chapter titled "Invasion of the Yokel-Snatchers" in which he was working with Kang and Kodos.

[37] An early version of the script for "Krusty Gets Busted" called for James Earl Jones to voice Bob, but the producers instead selected Kelsey Grammer.

[45] For season three's "Black Widower", the writers echoed the premise of Wile E. Coyote chasing the Road Runner from Looney Tunes cartoons by having Bob unexpectedly insert himself into Bart's life and attempt to kill him.

Executive producer Al Jean has compared Bob's character to that of Wile E. Coyote, noting that both are intelligent, yet always foiled by what they perceive as an inferior intellect.

[36] A rule for earlier episodes featuring Bob called for a recap of his evil deeds; this was dropped after season eight's "Brother from Another Series" when the chronology became too lengthy.

[49] Despite these challenges, however, creators of The Simpsons usually look forward to "Sideshow Bob episodes"; the writers consider them enjoyable to write,[50] and former director Dominic Polcino describes them as "a treat" to work on.

[53] In a 2007 interview, Simpsons executive producer Al Jean listed Grammer as one of his favorite guest stars (second only to Phil Hartman), saying "his voice is so rich.

[61] Cecil returns in season 19's "Funeral for a Fiend", which introduces the brothers' previously unseen father, Dr. Robert Terwilliger, played by John Mahoney.

[63] Whereas in Frasier, Mahoney played the "down-to-Earth, average guy" to Grammer's and Hyde Pierce's "uppity snobs", Robert Terwilliger Sr. was portrayed as equally highbrow as Bob.

In 2006, IGN listed him as the second-best "peripheral character" on The Simpsons, commenting that Bob is "a man of contradictions; his goofy appearance, complete with palm tree like hair, doesn't seem to match up to the well spoken and even musically talented maniac.

[67] Adam Finley of TV Squad wrote that "that baritone voice, the Shakespearean delivery, and the ability to go from calm and collected to stark raving mad all within the same second make Sideshow Bob one of the best recurring characters on the show.

"[9] In her book My Life as a 10-Year-Old Boy, Nancy Cartwright (who performs the voice of Bart Simpson) wrote that "Kelsey Grammer scores big-time by injecting caustic, bitter, contemptuous and deliciously vile energy into his rendition of Sideshow Bob.

[80] In Planet Simpson, author Chris Turner writes that Bob is built into a highbrow snob and conservative Republican so that the writers can continually use him as a strawman and pincushion.

When accused of election fraud, he rants, "Your guilty consciences may force you to vote Democratic, but secretly you yearn for a cold-hearted Republican who'll cut taxes, brutalize criminals, and rule you like a king!