Fictional Characters Wiki

"Hello, Bart. (Bart and Lisa: Ahhh! Sideshow Bob!)"

  • Sideshow Bob's catchphrase and Bart & Lisa's response.

Robert Underdunk Terwilliger Jr, better known as Sideshow Bob, is one of the main antagonists (and sometimes an anti-hero) of the animated TV series The Simpsons. He is Bart Simpson's archenemy.

Sideshow Bob used to be Krusty's sidekick and best friend and co-star of the Krusty the Clown Show, but soon he was so tired of being humiliated by Krusty and wanted him off TV.

He was originally Krusty the Clown's sidekick until he framed Krusty for robbing the Kwik-E-Mart, however he was foiled by Bart Simpson who exposed Bob's scheme. And ever since then Bob has vowed to kill Bart, though on some occasions he has also gone after Krusty.

He is voiced by Kelsey Grammer in his first villain role as he late played Stinky Pete in Toy Story 2, Harold Attinger in Transformers: Age of Extinction, and Hunter in Storks.


Sideshow Bob is a complex character in the series. He is a sadistically obsessed psychopath by trying to kill Bart, yet he is often very smart and sophisticated to talk, and has shown redeeming features in the past such as deciding against killing Krusty when he realized that he regretted mistreating him (which led to his start to villainy).

Sideshow Bob enjoys the finer things in life, including reading classical literature and possesses massive. Likely due to his upbringing, he has a passion for theater, knowing Gilbert and Sullivan's H.M.S. Pinafore off by heart as well as Shakespeare's works. In contrast to his love of the 'higher pleasures', he despises television and other 'low class' things, which gives him a rather snobbish attitude. Ironically, in his time when he was a Master Criminal, he studied the uses of Dynamite, which would theoretically be considered low class. At times, he also may have genuine desires to help humanity, as he explains that his motivation for tricking the Springfield citizens into electing him was to "save them from themselves."

Beneath the cultured gentlemen is the heart of a cold blooded killer; Bob is a man who is willing to hurt others to get what he wants. Bob's primary motive seems to be revenge; his original crime (framing Krusty the Clown) was an attempt to get back at him for making a clumsy fool of Bob for years as his sidekick, and most of his other crimes have been more evil attempts at murdering Bart Simpson for foiling him. However, he has made several attempts at acquiring money and/or power not related to his vendetta against the two of them, such as when he tried to kill Selma Bouvier (though since Selma was not well-liked, this was a bit justified) or run a campaign for mayor as a republican (if for no other reason than to make the Simpsons miserable).

Bob's rivalry with Bart

He is Bob's rivalry with Bart Simpson on some of his episodes. The underlined episodes are where Bob serves as the main antagonist of that episode.

Krusty Gets Busted

The rivalry between Bart and Sideshow Bob began in the season 1 episode, Krusty Gets Busted, when Bob framed his partner Krusty for robbing the Kwik-E-Mart with a gun. A man named Homer Simpson was there when Bob committed the robbery, and reported Krusty to the police, and got him thrown in jail. After Krusty's arrest, Bob gained control of the Krusty the Clown Show, renaming it Sideshow Bob's Cavalcade of Whimsy. Fortunately for Krusty, Homer's son Bart foiled the scheme after realizing that Krusty could not be responsible for the crime and he exposed Bob committed the crime dressed like to the audience by revealing that, like the Kwik E Mart robber, he had abnormally large feet, and Krusty was released while Bob was thrown in prison. This began Bob's rivalry with Bart as he swore revenge on Bart for this.

Black Widower

In the season 3 episode, Black Widower, For his next evil plan, he was released from jail and married Bart's aunt Selma. Later, he tried to blow her up to gain her inheritance from the stock market, but Bart caught on to his plan and Selma was rescued and Bob was arrested again.

Cape Feare

Later In the season 5 episode, Cape Feare, Sideshow Bob began sending death threats to Bart in the mail. Bob was later released and drove around an ice cream truck reading a list of the people he would spare (Bart was not on the list). In response, Bart and his family moved from Springfield to another town and changed their surname to Thompson. However, Bob latched himself onto the Simpson's car and resumed his pursuit after Bart, but was hit by rakes, which allowed Bart to flee and alert his parents. Later that night, Bob located the family in a boat used as a home and upon boarding, he cut the rope holding the boat to the dock and tied up Bart's parents and sisters. Bob eventually cornered Bart on the port, but Bart stalled for time by distracting Bob long enough for the boat to reach Springfield. Bart's plan to defeat Bob again was successful, and the police freed Bart's family after the boat arrived in Springfield and arrested Bob yet again.

Sideshow Bob Roberts

In the season 6 episode, Sideshow Bob Roberts, Bob was released again and ran against Mayor Quimby for mayor of Springfield (with the help from Mr. Burns and the Springfield Republican Party). Bart and his sister Lisa ran for Quimby, but despite that, Bob rigged the election against Mayor Quimby by putting in dead people and pets as people who voted for him and won the election. After becoming mayor, Bob put the Simpson's house in front of his expressway to demolish it and demoted Bart to kindergarten. Bart and Lisa desperately tried to find evidence that Bob rigged the election, to no avail. However, Bart discovered one of the names of the people who voted for Bob on a tombstone with help from Waylon Smithers. Bart and Lisa placed charges against Bob and put him on trial, where they tricked him into confessing his crime and Bob was arrested. His evil plans had failed again.

Sideshow Bob's Last Gleaming

Later In the season 7 episode, Sideshow Bob's Last Gleaming Bob was placed on duty in a local Air Force Base, but escaped and stole an A-bomb to threaten Springfield to rid itself of television, and the Air Base was evacuated, but Bart and Lisa were separated from their parents and decided to stop Bob. The National Guard soldiers searched for Bob, but were unable to locate him. Bob was broadcasting from an airship and was able to evade capture easily. However, Bob discovered that Krusty began televising himself from a fallout shelter in the desert. This outraged Bob, but not before Bart and Lisa tracked him in the cockpit. Angry, Bob attempted to detonate the A-bomb, but it turned out to be a dud and did not explode. Lisa quickly used the airship's electronic ticker to send a message to the police. When the police tried to capture Bob, Bob kidnapped Bart and deflated the airship. Bob then stole the Wright Brother's plane to escape and crash into Krusty's shelter. However, Bart freed himself and Bob crashed the plane near the shelter where the police arrested him.

Brother from Another Series

In the season 8 episode, Brother from Another Series, Bob was the secondary antagonist/anti-hero. He was released into the care of his younger brother Cecil, who began constructing a dam. Bart and Lisa snuck in to investigate, but Bob caught them and returned them to their parents. However, Bob, Bart and Lisa learned that Cecil is planning to flood Springfield by blowing the dam and frame Bob for it to cover his embezzlement (mostly out of spite against Bob for being chosen as Krusty's sidekick), Having no choice, Bob, Bart and Lisa were forced to work together to stop Cecil from flooding Springfield. However, as the police arrest Cecil for his crimes, they believe that Bob is involved in the plot and arrest him as well, even though the plan was entirely Cecil's doing. Cecil then tricks Bob into swearing revenge on Bart and Lisa, thereby incriminating himself once again, much to his horror. As such, Bob gets angry at Cecil for making him become Bart's nemesis again.

Day of the Jackanapes

In the season 12 episode Day of the Jackanapes, Bob escaped prison and tracked down Bart to Springfield Elementary School and lured him into a shed where he hypnotized him. Bob planned to use Bart to kill Krusty. Eventually, Bob strapped explosives to Bart to kill Krusty and kill Bart himself so Bob could finally have his revenge. However, Krusty's monkey detached the explosives and destroyed Bob's chamber, which also forced Bart out of his hypnotic state. Though Bob makes amends with Krusty and apologized for the attempted murder, he was arrested.

The Great Louse Detective

"Tom Shales gave this show a good review. And I'm the one IN PRISON!"

  • Bob's review on That 30's Show

In the season 14 episode, The Great Louse Detective, Bob served as the secondary antagonist/anti-hero. He was released to help the Simpsons find out who was trying to killing Homer, despite Bart's concerns. In order to prevent him from killing Bart, The police chief Clancy Wiggum attached an electric collar to Bob's leg and gave the Simpsons it's remote so they could shock him with it. Wiggum taped it to Bob's hairy leg so Bob would not take it off because it "really hurts". Eventually, Bob discovered the assassin was Frank Grimes, Jr., the son of Frank Grimes, Homer's co-worker in the season 8 episode Homer's Enemy. Grimes Sr. hated Homer and accidentally electrocuted himself to death while mimicking Homer's habits. His son wanted revenge on Homer for killing his father. But Bob and Homer caught Frank and he was arrested. After Frank's imprisonment, Bob returned to his goal to kill Bart, and attempted to murder him in his own room, but didn't because he had "grew accustomed to his face". After singing a song, He let Bart go and went out his window ready to escape in the shadows, but the bird activated the shock remote that Bob threw out earlier, and electrocuted Bob.

The Italian Bob

It is revealed in the season 17 episode The Italian Bob that Bob fled to Italy and married a Italian woman named Francesca, and they had a son named Gino. Eventually, Bob became mayor of a Italian village after they realized how effective his large feet were at making wine. In the episode, The Simpsons soon arrived there to buy a new car for Homer's boss, Mr. Burns, and once again ran into Bob, who begged them not to expose him. However, Lisa became intoxicated with wine and exposed Bob's criminal past of the village, which infuriated Bob, and he swore vendetta on the Simpsons. Bob pursued the Simpsons on a Ducati, but failed to catch them. Later, Bob cornered the Simpsons in the Colosseum with his family, but the Simpsons were rescued by Krusty and they returned to the U.S., leaving Bob stranded in Italy.

Funeral for A Fiend

Eventually in the season 19 episode Funeral for A Fiend, Bob snuck into the U.S. where he lured the Simpson family to a fake restaurant called "Wes Doobner's World Famous Family Style Rib Huts" and dressed up like it's cowboy owner, Wes Doobner. After Bob trapped the Simpsons in the restaurant, revealed his true identity and tied the family to chairs, Sideshow Bob reveals he will kill the family with a large pile of TNT, which he'll set off using a laptop with a defective battery, which will overheat and explode. While gloating, Bob incorrectly quotes a phrase from Macbeth and Lisa corrects him and says the correct quote. Bob sets up the bomb and leaves the room but Lisa urges him to come back in and look up the Macbeth quote on the laptop. He returns and tries to use the laptop to find the correct phrase on Wikipedia, but the laptop explodes in Bob's hands. He is then arrested and taken to court. However, Bart was put on trial as well by Bob. Bob's father, Dr. Robert Terwilliger Sr., is brought to testify. He explains Bob has a rare heart condition, and also suggests that Sideshow Bob is insane because of his long-standing feud with Bart. However Bart calls Bob out on his lies and demands he be returned to jail. Bob then pulled up what appeared to be an explosive, but Bart threw it out the window. Bob then collapses on the floor. Bob's mother - Shakespearean actress Dame Judith Underdunk says that what Bob was holding was medicine for his heart medication and Dr. Hibbert walks over, examines Bob and says that Bob is dead. At Bob's funeral, his brother Cecil insists Bart pays his respects to Bob before he is cremated. Bart visits Bob at his coffin however to his surprise, Bob pops out of the coffin alive and well and throws Bart into the coffin. Meanwhile at the Simpson house, Lisa discovered that Bob faked his death and his family planned the whole thing out. Bob is getting ready to cremate Bart, but the Simpsons arrive with the police and rescue Bart and arrest Bob. When Bob asks Lisa how she figured out he faked his own death, she explains that she was suspicious that Bob's coffin had extra room for his large feet, which the family would not have bothered to pay to have put in "for the comfort of a dead man". Bob and his family are later locked with Snake Jailbird.

Sex, Pies and Idiot Scrapes

Bob briefly appeared the episode escaping from Springfield Penitentiary, where Homer is sent to for a day after skipping bail for his role in a St. Patrick's Day brawl.

Wedding for Disaster

Bob appeared in Wedding for Disaster, where Homer was kidnapped from attending his second wedding ceremony with Marge (as their marriage was declared invalid due to a lapsed ministerial certification held by Rev. Lovejoy). At first, Bart and Lisa initially suspected Sideshow Bob as he escaped from prison and that they found a keychain with the initials "S.B.", so they confront him for kidnapping their father. However, it turns out that Bob is innocent, as Krusty gave an alibi that he was with Bob the whole time when Homer got kidnapped. Eventually, Bob soon deduced that the keychain actually belonged to his ex-wife Selma, the very same person he tried to kill for her money. It was then Bart and Lisa realized that Patty and Selma kidnapped Homer and planned to keep him cooped up until Marge forgets about him. At that point, Bart and Lisa confront their aunts and threaten to tell their mother about what really happened, forcing both Patty and Selma to concede defeat and pay for the remarriage ceremony. Despite Bob's innocence being proven, he was last seen sent back to prison for unknown reasons.

The Bob Next Door

"Bob: The sum total is the greatest murder since Snape killed Dumbledore!
Bart: I haven't gotten to that part yet!
Bob: It's a four year old book."

  • Bob spoils a major part of the Harry Potter and the Half Blood Prince novel for Bart.

Later in the season 19 episode The Bob Next Door, Bob's cell mate, Walt Warren, was scheduled for release, so Bob drugged him unconscious. Bob used plastic surgery to switch his face with Warren's face. Using Warren's identity, Bob escaped prison while Warren stayed in prison, as the police mistook him for Bob. Bob then bought the house next to the Simpson's house, but Bart immediately discovered who he really was. Bart made several attempts to blow Bob's cover, but with little success. Later, his mother Marge took Bart to see Bob, who was really Warren, still in jail, which appeared to satisfy his concerns. That night, Warren escaped from jail to alert the Simpsons of the danger. Later, Bob bought an extra ticket to the baseball game. Bart agreed to go and went to get his cap. Bart then left with Bob in his car, where Bob revealed he was indeed who he was and proceeded to take Bart to Five Corners to kill Bart. Once he arrived at Five Corners, Bob revealed his plan: Bob would stand in one state, fire his gun in the second state, where the bullet would travel through the third state, hitting Bart in the fourth state, and Bart falls dead in the fifth state, so his murder cannot be prosecuted and even quotes greater than when "Snape killed Dumbledore." However, Warren, attacks Bob and stopped him. The police then arrived to capture Bob, and Chief Wiggum revealed that Bart was never truly convinced that Bob was Warren, and before his capture, Bart reported to the police about Bob and told them to track the car. However, Bob jumped to the others state, but more police appeared there as well. Eventually, Bart was freed and Bob was arrested and Warren with them to return their faces to normal, and Bob was seemingly placed in high security shortly after.

At Long Last Leave

In the Season 23 episode, At Long Last Leave, the show's 500th episode, he later speaks briefly during the town meeting to banish the Simpson family from Springfield.

Moonshine River

In the season 24 premiere Moonshine River, he attempts to kill Bart while in New York City, only to be hit by a train.

Dark Knight Court

In the other season 24 episode Dark Knight Court, Bob was later seen during Bart Simpson's trial, assuming the mantle of one of the "Unfriendly Witnesses".

The Man Who Grew Too Much

In the season 25 episode, The Man Who Grew Too Much, While still serving out his sentence at Springfield Penitentiary, Sideshow Bob was recruited as a human test subject by Monsarno Corporation. His original purpose was to ensure that the experiments wouldn't be too painful for the test monkeys. After publishing the results of the tests he was subjected to, he eventually rose up the ranks to become Chief Scientist at the Monsarno Research Campus, where he created over 5000 patents. One day, the Simpson family visits the lab to learn more about genetically modified organisms and are shocked to find Sideshow Bob working there. Bob swears that he has changed and that he truly is working to make a better world. During their visit, Lisa learns that she and Bob share a common passion for Walt Whitman, poetry, and art. Believing that a mind that thinks so much like hers could not possibly be completely evil, she begins visiting Bob at the campus on a regular basis. Eventually, Monsarno Corporation allows Bob an hour of freedom to spend with Lisa at the Springfield Metropolitan Museum. While there, a Calder Mobile almost falls on Lisa, but Bob saves her by catching the mobile and throwing it aside. When Lisa demands to know how Bob got the strength to lift the massively heavy sculpture, Bob confesses that he had been altering his DNA to give himself various superhuman abilities. Further, he admits that he had only come to the museum to collect DNA from the personal effects of famous historical persons (such as George Washington, Albert Einstein, and Florence Nightingale) and splicing them with his own so that he might become a superhuman dictator. Eventually, Bart shows up at the museum and Bob is provoked to attack the Simpson children, due to DNA from Zombie Ant Fungus. During the chase scene that follows, Bob demonstrates the abilities of grasshopper-like leaping, sonar, and cranial kinesis. He eventually corners the children at the Springfield Dam and intends to throw them off of it. However, when Lisa recites a quote by Whitman, Bob finally realizes what kind of person he has become and attempts suicide by leaping from the dam himself. He survives on account of having given himself gills.

Clown in the Dumps

In the season 26 premiere Clown in the Dumps, When Krusty's father dies, Bob makes a brief appearance at the funeral reception to offer his condolences to Krusty. He is then confronted by a drunken Sideshow Mel, who reveals that Krusty is always telling him that he will never live up to Bob's comedic genius. Mel goes on to say that all of Krusty's sidekicks have thought about killing him.

Blazed and Confused

Later, In the other season 26 episode, Blazed and Confused, Bob meets Jack Lassen, a sociopath who took a job as a prison guard at Springfield Penitentiary after Bart gets him fired from his job as the new fourth grade teacher at Springfield Elementary. Realizing that they both share a deep hatred of Bart Simpson, Lassen offers to break Bob out of prison so they can team up and take their revenge on the boy together. Bob ultimately rejects the deal as he does not want to have to take turns gutting Bart.

Treehouse of Horror XXVI

In the first segemt of the season 27 episode, Treehouse of Horror XXVI, he seems to trapped Bart with a text on Milhouse cellphone, he tell Bart he will finally kill him with a gun, Bart tell he could not kill him same with a X on his head, but Sideshow Bob shot him in the heart and successfully killing him, but after Lisa and her family found Bart body and revived him, Sideshow Bob show up with a gun before be beheaded by Homer, Bart revived him, but on the body of a frog.

Treehouse of Horror XXVII

In the opening scene of season 28 episode, Treehouse of Horror XXVII, the show's 600th episode, he teams up with other Simpsons villains to crush the family. The villains he enlists are Kang, the ghost of Frank Grimes Sr. and Lepurcon. However Maggie kills them all. One of the villains who was with him in the promo was Russ Cargill from The Simpsons Movie.

Other Media

  • Bob also has a brief cameo in the Simpsons/Family Guy crossover episode, as one of many of Bart's enemies (along with Apu) that Stewie Griffin kidnaps and tortures.
  • Sideshow Bob is the main antagoist on the ride at Universal Studios, The Simpsons Ride. While Krusty was looking for a family to choose to be the first one to try out his all new, Upsy-Downsy-Spinsaroundsy-Teenoperatied Thrill Ride, Bob steps on Homer's foot causing him to shout, "D'OH!". This causes Krusty to choose the Simpson Family and also allows them to pick another group to come with them, which Bart chooses the audience. Sideshow Bob laughes evilly as the Simpson Family goes with Krusty as he was planning to use Krusty's new thrill ride as part of his new plan to kill the Simpsons for foiling him. Bob knocks out Krusty when the Simpsons were in the vehicle boarding station and then takes over the park and tries to kill the family (and the audience) while they crashed through different parts of Krustyland. But at the end of the ride, Sideshow Bob gets crushed by the Simpsons' couch when the family fell down the death drop. It's unknown what happened to him after that, but probably he was then caught and arrested and sent back to jail.