The Best Sideshow Bob Episodes From The Simpsons

“Very well, Bart. I shall send you to heaven before I send you to hell.”

With new Simpsons episodes still being churned out and unfortunately, none of these are any good or worth talking about we thought we’d instead take a look at the episodes of one of our favourite characters from that once great show… Sideshow Bob.

Who is Sideshow Bob?

Dr. Robert Underdunk “Bob” Terwilliger Jr., PhD, better known as Sideshow Bob, is a guest character in the animated television series The Simpsons. Voiced by Kelsey Grammer (Frasier) and first appeared in the episode “The Telltale Head”. Bob is a self-proclaimed genius who is a graduate of Yale University, a member of the Republican Party, and a champion of high culture. He began his career as a sidekick on Krusty the Clown’s television show, but after enduring constant abuse, Bob framed his employer for armed robbery in “Krusty Gets Busted”, only to be foiled by Bart Simpson, and sent to prison. Bob started seeking revenge against Bart while in prison, and the two became feuding arch-enemies.

From our previous reviews of Simpsons episodes, all the best episodes feature pre-season 10 so we expect this list to go no different.

Take a look at our top 25 Simpsons episodes (which will be revisited and may be revised later this year) and also our favourite Treehouse of Horrors episodes.

Also, why not check out our list of previous Simpson’s articles here.

We start with…

15. The Italian Bob – Season 17 – Episode 8

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In “The Italian Bob”, we catch up with Bob after he has moved to Italy to make a fresh start. He has been elected mayor of the village of Salsiccia in Tuscany and has married a local woman named Francesca, with whom he has a son named Gino. The Simpson family are in Italy to retrieve a Lamborghini supercar for Mr. Burns, and they encounter him by chance. Bob welcomes them with hospitality on the condition that they do not reveal his dark felonious past; however, a drunken Lisa jokes about Bob’s criminal deeds and reveals his prison uniform, alienating Bob from his citizens. Bob is angered enough to change his dream of killing Bart to killing the whole Simpson family. Upon catching up to Bob, his wife and his son swear a vendetta with him on all the Simpsons.

14. The Man Who Grew Too Much – Season 25 – Episode 13

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In “The Man Who Grew Too Much”, Bob was revealed to be 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 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. After being tempted into a murderous rage, he chases down Bart and Lisa and is about to kill them but however, but he is provoked into a fight and he realizes that he has become a crude monster and jumps off the Springfield Dam. The episode ends with Bob underwater in the lake, shown to have survived because the gills he gave himself allowed him to live.

13. Gone Boy – Season 29 – Episode 9

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In “Gone Boy”, Bob tries to track down the whereabouts of Bart after he goes missing and is presumed dead. Bob finds Bart and proceeds to kill him and Milhouse, but saves them at the last minute due to the influence of the prison therapist’s lessons of potentially moving on from wanting to kill Bart. The epilogue features an older Bob, now known as Elder Bob, being a lighthouse keeper and still having regrets about not killing Bart.

12. Funeral for a Fiend – Season 19 – Episode 8

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The entire Terwilliger family appear in “Funeral for a Fiend” in which Bob’s father, Robert Terwilliger Sr., and mother, Dame Judith Underdunk, make their first appearances. Cecil also appears a second time on the show. Bob at first attempts to kill the whole family a second time, but his plan fails. 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. They are foiled by Lisa and the rest of the Simpson family and sent to prison.

11. The Bob Next Door – Season 21 – Episode 22

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Bob reappears once again in the episode “The Bob Next Door”. This time 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

10. Bobby, It’s Cold Outside – Season 31 – Episode 10

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In “Bobby, It’s Cold Outside”, Bob is hired to play Santa Claus at a theme park, and later helps the Simpsons discover who is stealing everyone’s Christmas gifts.

9. Treehouse of Horror XXVI – Season 27 – Episode 5

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In “Treehouse of Horror XXVI”, in the first story called “Wanted: Dead, then Alive”, Bob uses Milhouse’s phone to trap Bart in the band classroom and successfully kills him. In peace with himself, Bob moves on from Bart to pursue other dreams, however, due to Bob chasing down Bart for so long, Bob 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 find Bob’s location and rescue Bart, and Bart uses the resurrection machine to turn Bob into a twisted amalgamation of creatures.

8. The Great Louse Detective – Season 14 – Episode 6

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Bob’s aid is sought by Springfield police in “The Great Louse Detective”. After an attempt is made on Homer Simpson’s life, Bob is released from prison to help find the culprit. During the adventure, Bob is given the advice to kill Bart without hesitation, instead of being tricked into delaying or screwing up his plots. When the mystery is solved and it is revealed that it was Frank Grimes’s (or Grimey as he liked to be called) son, he returns to murder Bart. However, Bob finds he is “accustomed to his [Bart’s] face” and cannot do it.

7. Day of the Jackanapes – Season 12 – Episode 13

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In “Day of the Jackanapes”, Bob discovers in prison 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. Everything goes just as Bob had planned, and just when Bob was about to succeed in murdering both his enemies, 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.

6. Krusty Gets Busted – Season 1 – Episode 12

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It’s Bob’s first major outing In “Krusty Gets Busted” from the first season, all the way back in 1990. Here Bob disguised himself as Krusty and frames him for the armed robbery of the Kwik-E-Mart. After Krusty is arrested, Bob takes control of the show and introduces the viewing children to elements of high culture that they never got before. However, Bob’s reign is short-lived; Bart exposes him as the robber, Krusty is released, and Bob is fired and sent to jail for the first time!

5. Black Widower – Season 3 – Episode 21

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Bob’s first major reappearance 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, but Bart again foils the plan and Sideshow Bob returns to prison.

4. Brother from Another Series – Season 8 – Episode 16

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Bob takes advantage of the prison’s work-release program and appears to be genuinely redeemed. “Brother from Another Series” reveals that Bob only became Krusty’s sidekick after his younger brother Cecil failed an audition ten years prior because Krusty considered Bob to be a perfect comic foil. Reverend Lovejoy declares him a changed man and recommends him for a work release opportunity. Bob is discharged from prison into the care of Cecil, who is now 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 by having it burst across Springfield. Bob, Bart, and Lisa together stop Cecil and save the town, and both brothers, despite Bob’s genuine innocence, are sent to prison

3. Sideshow Bob Roberts – Season 6 – Episode 5

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Bob is released from prison once again in “Sideshow Bob Roberts”, 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 from Waylon Smithers that Bob rigged the election by using the names of deceased people. Bob is put on trial and claims himself innocent, but is tricked by Bart and Lisa to expose himself as guilty, leading to another incarceration

2. Sideshow Bob’s Last Gleaming – Season 7 – Episode 9

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Sideshow Bob escapes from prison for the first time in “Sideshow Bob’s Last Gleaming”, 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, improvising a performance on the Emergency Broadcast System). This too is thwarted, and Bob returns to prison

Finally… Our Fave Sideshow Bob Episode

1. Cape Fear – Season 5 – Episode 2

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This is our favourite Sideshow Bob episode and also one of our favourite Simpsons episodes… The whole episode is a parody of Cape Fear. After being paroled from prison in “Cape Feare”, 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. Although Bob finishes singing and nearly kills Bart, the delaying tactic leads to Bob’s third arrest as the houseboat drifted all the way back to Springfield. Watch out for the rake scene!

Other appearances

In “Sex, Pies and Idiot Scrapes” – Season 20, 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. In “Wedding for Disaster” – Season 20, 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

In “O Brother, Where Bart Thou?” – Season 21, Bob makes a non-speaking cameo appearance in Bart’s dream sequence while the latter becomes desperate of having a younger brother. Cecil makes his third appearance in The Simpsons by appearing alongside Bob; the brothers are flying kites together.

Bob appears in “At Long Last Leave” – Season 23, the 500th episode of The Simpsons. He attends a town meeting to decide if the Simpson family should be banished from Springfield, and is one of many who express their desire for it to happen. He makes a silent appearance in “Moonshine River” – Season 24, where he runs across the train tracks trying to kill Bart, but ends up getting hit by a train.

Bob also appears in “Clown in the Dumps” – Season 27. Having returned to prison, he offered his condolences to Krusty after the death of his father, Rabbi Krustofsky. Several episodes later, Bob returned in “Blazed and Confused” – Season 26, where he meets Mr. Lassen, Bart’s former teacher, who was now reduced to working in prison as a guard after Bart’s earlier actions at a “Blazing Guy” festival got him fired. Despite Lassen’s offer to get him out, Bob rejects the idea that they team up as Lassen thought that they would take turns gutting Bart.

Bob also appears in the episode “Gal of Constant Sorrow” – Season 27, 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

Bob returns in “Treehouse of Horror XXVII” – Season 28, the 600th episode of The Simpsons. 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. Wanting revenge once more, the group attempts to kill the Simpsons but is ultimately killed by Maggie, except Grimes’s ghost. In the ending sequence, Bob is one of the characters featured in the “600” song played by Judith Owen. In “Havana Wild Weekend” – Season 28, Sideshow Bob appeared in the background at the Cuba’s check-in.

Bob also makes a non-speaking cameo appearance in “The Nightmare After Krustmas” – Season 28; he is amongst the crowd witnessing Krusty nearly drowning in a frozen lake while holding up a sign saying “Die Clown”.

In “The Fat Blue Line” – Season 31, Bob escapes from prison once again, only to be hit by a rake truck.

Bob returned in a non-speaking cameo in “Meat Is Murder” – Season 33 , where he is seen signing the chests of citizens like Milhouse’s father Kirk Van Houten at the celebration of Krusty Burger’s 50th anniversary, a callback to the “Die Bart, Die” scene from “Cape Feare.”

Written by Jay

A caffeine-based life form with a love of the 80s and pop culture.

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