- For Sideshow Bob's father, see Robert Terwilliger, Sr. For other uses, see Sideshow Bob (disambiguation).
- “Hello, Bart.”
- ―Sideshow Bob
Dr. Robert Underdunk “Bob” Terwilliger, hJr., more commonly recognized by his stage name, Sideshow Bob, is the secondary antagonist of The Simpsons and a minor antagonist in The Simpsons Movie. He was originally Krusty the Clown's sidekick before starting a life of crime that began with an attempt to frame Krusty for armed robbery. Bob is a self-proclaimed genius, member of the Republican Party, champion of high culture, former children's entertainer-turned-criminal mastermind and Bart Simpson's nemesis. He loves operettas, the likes of Gilbert and Sullivan, and is also known for his gigantic feet, which have gotten him into trouble on more than one occasion.
- 1 Biography
- 2 Non-Canon Appearance
- 2.1 Future
- 2.2 Halloween Specials
- 2.3 Treehouse of Horror XXVII
- 2.4 The Simpsons Guy
- 2.5 Ride
- 2.6 Video-Games
- 2.7 Mobile Games
- 3 Behind the Laughter
- 4 Trivia
- 5 Appearances
- 6 Gallery
- 7 Citations
Robert Terwilliger (aka Sideshow Bob) began his career as "Sideshow Bob", a non-speaking sidekick on Krusty the Clown's television show. His younger brother, Cecil, was actually the one who was auditioning for the role, which Krusty was not impressed by and saw Bob as the ideal comic foil who would be ridiculous and never stand him up. Sideshow Bob endured much as it was to be expected from being clown sidekicks, such as being targeted with pies and shot out of cannons, but Krusty took on a more sadistic bent in order to get laughs, which had been shown to be a habit of doing to other sidekicks of his. Sideshow Bob soon began to tire of these antics, and also realized that off-camera Krusty was engaging in vulgar behavior such as illegal gambling and patronizing strip joints. Fed up with enduring abuse in order to make money to fund Krusty's carnal appetites, Sideshow Bob began plotting Krusty's downfall.
Fed up with Krusty's torment, Bob disguised himself as Krusty and framed him for an armed robbery of the Kwik-E-Mart. After Krusty was arrested, Bob takes control of the show, introducing children to elements of high culture. However, Bob's reign is short-lived; Bart Simpson, with the help of his sister, Lisa, exposes Bob's treachery and Krusty is released. Bart, with Lisa's help, was able to catch Bob mainly because Bob's large feet actually filled out Krusty's clown shoes, so when his foot was stepped on in the security footage he felt it and yelped. Had it actually been Krusty committing the robbery, he would not have felt his foot being stepped on (or he may have worn normal shoes to aid in his getaway). Bart and Lisa also knew that Krusty had a pacemaker and in the security footage Bob used the microwave, which the real Krusty could not do because it would interfere with his pacemaker. Finally, Krusty was illiterate and Bob was reading a magazine in the Kwik-E-Mart right before committing the robbery. After the new evidence was brought forward, Bob was subsequently convicted for the robbery and sent to jail, but not before swearing vengeance on Bart.
During his time in prison, Bob won an Emmy Award for his role on The Krusty the Clown Show, but his award was confiscated by the prison guards. Bob took part in a prisoner dating service and went into a relationship with Selma Bouvier, Bart's aunt. He also took some satisfaction in making nameplates for cars during this time since it allowed him to make subtle threatening messages against Bart. After he was released from prison, he proposed and married Selma, despite Bart's protests. As part of a scheme to inherit the money she has invested in the stock market, Bob attempted to kill Selma by blowing up their hotel room during their honeymoon. However, Bart again foiled the plan and Sideshow Bob returns to prison, exclaiming that as soon as the Democrats were back in office, he and all his criminal buddies would be back on the streets. Ironically, he would run as a Republican in a later episode.
After being paroled from prison, Bob targeted Bart directly, threatening him repeatedly. His first attempt at threatening Bart involved mailing dozens of threatening letters written in Bob's own blood (only one of the letters was not actually written by Sideshow Bob, written in a sloppy, grammatically-incorrect manner and obviously not being written in blood, which was instead written by Homer as revenge for Bart tattooing his butt with "Wide Load"), which also caused him some health problems due to blood loss. The letters led Bart to become extremely paranoid. Bob eventually managed to get parole due to manipulating the Parole Jury with his intellect and cultured nature. He then unveiled his release to the Simpsons family in a movie theater and then proceeded to declare all the people he won't be killing, making sure to leave Bart off the list. His actions forced the Simpsons to move to Terror Lake with the identity of the Thompsons as part of the Witness Relocation Program. Bob, however, anticipated their relocation and followed them to their new houseboat, although the actual journey proved painful for Bob, having his head hit repeatedly by speed bumps, being scalded by coffee Homer threw out of the car, and being subject to cacti after the family decided to drive through the cactus patches, and then after getting out of the car, constantly hitting rakes. He eventually encountered Bart underneath another car but ended up losing his quarry due to the arrival of a parade celebrating Hannibal crossing the Alps, complete with elephants, although not without Bart noticing his presence. Eventually, he, after infiltrating the houseboat and subduing the family, prepared to kill Bart. He allows a final request, however, and Bart asks to hear the entire score of H.M.S. Pinafore. This delaying tactic leads to Bob's third arrest.
Bob was released from prison once again after conservative commentator Birch Barlow convinced the public that Bob was a political prisoner. After being released, he ran for Mayor of Springfield on a Republican Party ticket. He won the election against liberal incumbent Joe Quimby by a landslide. He then used his power as mayor to propose the demolition of the Simpsons house to make way for an Expressway and sent Bart back to Kindergarten. Bart and Lisa later discover that Bob rigged the election, and then manipulated him into confessing after implying he was simply a patsy, leading to another incarceration.
During his prison sentence, he began to develop a growing dislike of television, calling it "an omnidirectional sludge pump, droning and burping". While doing community service at an Air Force Base before an annual air show, Bob escaped from his work duty and sneaks into a hangar in the base disguising his voice with the mannerisms of Col. Leslie "Hap" Hapablap, where he made off with a Nuclear device. During the air show, coincidentally being attended by the Simpsons family, Bob appeared on the television screens and threatened to blow up Springfield with a nuclear bomb unless the city stops broadcasting all television shows. When confronted by Bart and Lisa, the bomb is discovered to be a dud, and Sideshow Bob instead kidnaps Bart and hijacks the Wright Flier, planning to crash the Flier onto a shack where Krusty was broadcasting an impromptu TV show. However, the plan fails, and Bob returned to prison.
During yet another prison sentence, Bob became a member of the prison's Christian outreach program and tried to be genuinely redeemed. Reverend Lovejoy declared him a changed man and recommended him for a work release opportunity. Bob is discharged from prison into the care of his brother Cecil, who was Springfield's chief hydrological and hydrodynamical engineer. Though Bart constantly investigated him and his job at the dam still made him show signs of bitterness and resentment, he tried to be a good man. However, the scheming Cecil, still sulking over his failed audition for Krusty, tried to frame Bob by sabotaging the Springfield Dam. Bob, Bart, and Lisa together stopped Cecil and saved the town. However, both brothers were sent to prison despite Bob's genuine innocence due to chief Clancy Wiggum's steadfast insistence about Bob's culpability despite all contrary testimony from Bart and Lisa.
When Krusty announces his retirement due to low ratings, Bob discovered from prison that Krusty has erased all of the early shows featuring Sideshow Bob. Bob is released from prison and developed a plot to kill Krusty. Using his new job as an intercom announcer at Springfield Elementary, he corners Bart in a shack off the school playground and hypnotizes Bart, planning to use him as a suicide bomber during Krusty's final retirement show. However, when he overhears Krusty express regret about mistreating him, Bob decides to abort his plan, and although he is returned to prison for attempted murder, Krusty thanks him due to the fact that his show's ratings soar back up every time Bob tries to kill him. Sideshow Bob, as a result of his attempted murder, was also originally going to be executed by the Guillotine, but Bob reminded Chief Wiggum that he was supposed to get a trial before committing the execution, causing it to be revoked and spend time in jail. At some point, he also participated in Marge's prison art class and ended up having a paper-mâché sculpt being done on his own face for unknown reasons.
After a murder attempt is made on Homer Simpson's life, Bob was temporarily released from prison to help find the culprit, much to the dismay and horror of Bart. To keep him from trying to hurt Bart, the police attach a shock garter to Bob's leg and gives the family a remote that shocks Bob at the push of the button, which proves effective. However, the family, mainly Bart, misuse the remote, shocking Bob just for being too smart. During the course of the case, Bob actually saved Homer after an attempt on his life. When the mystery is solved, he returned to the Simpsons home to murder Bart. However, Bob found that he was "accustomed to Bart's face" and cannot do it. Bob did not return to prison and decided to move to Italy in order to make a fresh start. After gaining fame for his wine (his exceptionally large feet made him a perfect grape crusher), he became the mayor of the town. He married a local woman named Francesca, with whom he has a son named Gino.
The Simpson family encountered him by chance after coming to Italy to retrieve a car for Mr. Burns. Bob welcomes them with hospitality on the condition that they do not reveal his felonious past; however, a drunken Lisa jokes about Bob's criminal deeds, eventually exposing Bob's past and causing Bob to be alienated from his citizens. He, his wife and son swear a vendetta on the Simpsons.
In a later attempt on Bart's life, Bob lured the Simpsons family into a fake rib restaurant, and tied the entire family up, planning to kill them with the explosion of an overheating laptop next to a pile of TNT. After Bob misquoted several lines on Shakespeare, Lisa managed to trick him into checking a line from a Shakespeare play on Wikipedia, resulting in the laptop exploding on his hands. During the trial, Bob's father, Robert Terwilliger, Sr., testified on the stand, explaining that Bob had a rare heart condition, and also suggests that Sideshow Bob is insane because of his long-standing feud with Bart. This convinced Springfield that in the long-run Bart is ultimately to blame, and they turn against him. As Bart pleads his innocence, Bob takes out a vial labeled nitroglycerin, which Bart snatches and throws out the window, thinking it was an explosive. The vial was actually Bob's heart medication and he collapsed on the floor, unconscious, and was pronounced dead. In reality, Bob was actually faking his death and put in a temporary death-like state, as his father injected him with an anesthesia. His entire family was assisting him to kill Bart. When a guilty Bart visits his coffin while being led by Cecil, Bob leaped out of the coffin and trapped Bart inside to be cremated inside the coffin. The Simpsons family saves Bart just in time by blinding Bob with unclaimed ashes. Bob's entire family, including his Italian wife and child, and his brother and parents, were sentenced to an 87-year prison term, and Bob was put in a straitjacket.
Sideshow Bob was briefly seen escaping from prison and visited Krusty the Clown for the week. Bart and Lisa traced Sideshow Bob to a cabin believing that he has kidnapped Homer Simpson (Homer went missing at Marge's third wedding and thought Sideshow Bob was the culprit due to a clue, a key-chain with the letters "SB" on it, being left in the groom's room.), only to discover that he was actually trying to aerate a bust of Krusty that he was sculpting. Krusty also explains that Sideshow Bob couldn't have kidnapped Homer Simpson because Bob was with Krusty the whole day. When Lisa questions him about the key chain, he explains that, although it's nice that they thought of him, the initials don't just pertain to him, and gives a list of people whom "SB" could refer to, including Selma Bouvier, the actual culprit. Eventually, he returns to jail again (exactly how is never explained), where he is bullied by Snake.
Later, the town of Springfield releases all minor offenders from the Springfield prison as a result of budget cuts. Sideshow Bob performs plastic surgery on his new cellmate, Walt Warren, one such offender, switching their faces (which he did in order to be released from prison early, as Walt, so he can kill Bart). He then buys the house next to the Simpsons, planning to pose as their friendly neighbor while waiting for the chance to kill Bart. However, while this disguise does fool the rest of the Simpsons, Bart easily sees through it, immediately recognizing Bob's distinctive voice. Bob then planned to take Bart over to the Five Corners so he could kill Bart in one state while standing in another state, so that it would be legal for him to kill Bart. However, the real Walt manages to foil his plan and the police from all five states trap him. It is revealed he has been given back his normal face when he later speaks briefly during the town meeting to exile the Simpson family, and later on, when he attempts to kill Bart while in New York City, only to be hit by a train. Bart also assumed his identity on an online poker game. Bob was later seen during Bart Simpson's trial, assuming the mantle of one of the "Unfriendly Witnesses".
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.
When Krusty's father dies, Bob makes a brief appearance at the funeral reception to offer his condolences to Krusty (exactly how he was captured or if his abilities have been removed is never explained). 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.
Later, 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.
Bob later did community service, although his hard work was wasted when the Simpson family destroyed the garbage by running into it via their rental car. After learning that Bart went missing, Bob volunteered alongside his other prison inmates and Shaquille O'Neal to find Bart, obviously, so he could try to kill him. After hearing that Bart was dead, he had trouble believing it, with his doubts being confirmed when Bart called the Simpson family and confirming he is alive. Bob then forces Milhouse to show them where Bart was located (being the only one who found the manhole Bart fell into). Predictably, he then shoves Milhouse down the manhole and prepares to use the military missile bunker's missiles to do away with his nemesis. However, he ultimately had a change of heart and spared them, presumably also bringing him to the surface. Bob subsequently returned to prison and underwent psychiatric help. At some point afterward, he underwent parole again, and eventually joined a Santa union at Santa's Village where he played Santa to hear kids' desires for Christmas. This eventually led to a very awkward moment when his next customer ended up being his nemesis, Bart, as well as trying to avoid the urge to strangle him due to needing to act in-character. After gift packages were reported to be stolen from porches across Springfield, and Lenny left a clue to the identity of the one responsible, Bart assumed Sideshow Bob was responsible and went to Santa's Village, only to discover that his "plans" referred to his life goals. Bob then offered to help Bart catch the one responsible for the thefts, and hid in a package to draw out the culprits, who turned out to be Smithers and Mr. Burns, who did their actions because the latter had a horrible Christmas as a child. Bob then tells him that he became strong during that Christmas.
Sideshow Bob has appeared in various Simpsons Comics
For example in issue 2 story "Cool Hand Bart" where Bart, Nelson, Jimbo, Dolph, Kearny, and Milhouse attend a seminar, called "Scared Spitless", which is held in Springfield State Prison and intended to scare trouble-making kids into shaping up. Chief Wiggum decides that all the kids attending the seminar should spend an hour in an actual prison cell. Bart and Milhouse are put in Bob's cell, and to avoid being killed, Bart climbs through the bars and into a van. The van winds up in a work-camp, where Bart is chained up with Bob. Bob escapes with Bart, and they leap onto a moving train. Until Bob is able to get onto the train himself, he is left bouncing on his end of the chain, repeatedly hitting his head on the ground. Soon, however, he climbs aboard and advances on Bart with murderous intent. Just as Sideshow Bob is about to kill Bart, Bart points out that he would have to drag his corpse around, because they are chained together. Postponing his plan to kill Bart, they walk through the swamp while Bart follows until they reach a hacksaw sale. They go in, but Bob is forced to hide his hair in a hat to keep from being noticed and identified. They realize that Wiggum is at the sale, and Bart sucks his hat off with a vacuum cleaner, revealing him to the police. Finally, Bob is arrested and Bart goes home safe.
He appears again in issue 11 "Fallen Flanders" where he somehow teams up with Kang and Kodos and together they abduct Ned Flanders and replace him with an evil clone. Ned's uncharacteristic behavior convinces Bart and Lisa to investigate alongside actor Rainier Wolfcastle who had previously encountered the aliens' clones, this turns out to have been Sideshow Bob's plan all along and the three are abducted. Eventually, the aliens are defeated and Sideshow Bob escapes on a helicopter he realizes too late is driven by Chief Wiggum.
He appears in issue 23 story "Bart de Triomphe" which introduces his nephew Neil.
He and his brother Cecil appear in jail together in issue 41, story "Bart Simpson and the Krusty Brand Fun Factory". Krusty gives Ralph, Barney, Bart, Nelson, Chief Wiggum, Grampa, Homer (disguised as Barney's mother) and Snake (claiming to be Nelson's parole officer) a tour of his new factory in a boat on a cherry soda river which includes a water slide. Unbeknownst to Krusty and the visitors, Sideshow Bob has hacked into Krusty's computer and he drops a giant cherry on the boat. Krusty escapes while everyone else is forced to take refuge in the frozen food division. Bob releases flying cyborg monkeys that attack the visitors. They try to fight back until Krusty arrives in a jet and saves them. Krusty gets revenge on Bob by knocking his jet into Bob's prison cell.
In issue 46 story "Angels with Yellow Faces" he was paroled from prison. Bob wanted to make more money, so he starts a small business-Sideshow Bob's VCR repair and pet sitting. In the back of the building was his school of crime- where he would teach other people to become criminals. He uses Nelson Muntz, Dolph Starbeam, Kearney Zzyzwicz, and Jimbo Jones to steal money from people all over town. Meanwhile, Bart photocopies his butt and is caught by Chief Wiggum. Wiggum knows about Bob's scheme, but he has no proof, so he tells Bart- "You won't get in trouble if you infiltrate his gang". Bart cannot say no and joins the gang. Bob is planning to kill him until Bart aces the test. Bob is very proud and says that he will do his master scheme the next day. Bart tells Chief Wiggum that he doesn't know what it is. The next day, Bob drives to the hospital, planning to kidnap Mr. Burns (who is only there because of his love of children's tender organs). Nelson pushes Mr. Burns into a fake ambulance, where Bob drives away, but the police stand in front of them. Bob believes Bart called them and prepares to kill Bart with a high powered drug. Bart shocks Bob, and the police take him away. Lisa says she called in the cops after following him here. They hug.
In issue 77 story "The Many Faces of Bob" He is released from prison but soon ends up in the hospital and gets a new face. After Bart and Lisa discover this they become worried as they do not know what he looks like anymore. They eventually discover this was exaggerated and his new face is basically exactly the same as before. He is knocked out by Sideshow Mel.
In issue 108 story "Big House Homer" Homer is framed by Mr. Burns and Smithers and made Sideshow Bob's cellmate (though Homer fails to recognize Bob at first), due to a common dislike for Bart, Homer and Bob become quick friends. Bob takes Homer on a tour of the prison and Homer points out a masked prisoner who Bob claims to be a nameless psycho. Bob reveals to Homer a plan to escape jail, Bob's secret tunnel is under the cell of the masked prisoner. When Homer and Bob get into the cell the prisoner asks if he can come along. Homer quickly jumps into the tunnel when the prisoner reveals he knows who Homer is. The prisoner chases Homer through the tunnel while telling him that he can't escape the past. Homer falls into a cavern full of crates, the prisoner jumps down and removes his mask revealing, Frank Grimes, Jr.. Grimes reminds Homer that he was sent to jail for attempting to murder Homer to avenge the death of his father, Frank Grimes. Mr. Burns and Smithers enter the cavern and reveal it's Burns' secret stash of rare paintings. Sideshow Bob falls through the hole in the ceiling and knock out both himself and Grimes. Homer blackmails Burns to get him out of jail, otherwise he blabs about the paintings, Burns agrees and Homer is set free, while Bob and Grimes are returned to prison.
In Issue #123 story "Bobbing for Vengeance" Bob becomes popular on the television series Big House Live that broadcasts live from the prison where they show Sideshow Bob is in the kitchen and cook a Flaming Vengeance, around the same time everyone seems to start trying to kill Bart. The next day the family is at home and watches Big House Live in which Sideshow Bob explains that he has help from his spiritual advisor and now he wants to make peace with the world and not kill a young boy. A picture of that spiritual advisor is on the screen and Lisa tells Bart that she recognizes him. Lisa and Bart start to looking at copies of the show and Bart and Lisa discover that they almost always see Sideshow Bob's spiritual advisor and he has a pocket watch, and they realize he is a hypnotist. They pause the DVD and find that in some seconds they show the text, Vote for Bob. Be Like Bob. They realize that Bob is using hypnosis with subliminal messages so anyone who sees the program wants to kill him. Bart becomes really scared and outside the door is the residents of Springfield who want to come to play with Bart, when they see Bart in the house, he escapes and they start chasing him. Bart manages to escape the crowd and he decides to dress up as Sideshow Bob and tell the mob to leave Bart now, but they realize that it's Bart and intend to kill him, but then came the real Sideshow Bob and with his hypnotist and he gets all of Springfield to forget what happened to want to kill Bart himself. Chief Wiggum then appears and tells them that like all reality shows there's a twist, there was never any parole, that was just a way for the city to save some money and get some criminals out of they temporarily overcrowded jail. But because they did not have to pay to feed him they even managed to save a few bucks on the side for the Police Retirement and Buffalo wing. Sideshow Bob realizing he's facing life in prison no matter what he does and Wiggum confirms that. Sideshow Bob then starts to hunt Bart at his home, and Bart asks for help from Homer, but he can't leave the TV, showing live the hunt between Bart and Bob.
A British version of Sideshow Bob makes a minor cameo in issue 208, 'Brit Simpson', on page 11. His name was Sideshow Bobby.
He has unusually large feet (they actually fill his over-sized clown shoes). Apparently, if he needs to disguise himself, he can actually fold his feet just to wear "normal" shoes. He is tall with slender limbs and a plump paunch. His favorite weapon is a carving knife, which he is regularly depicted holding. In the episode Cape Feare, he uses a machete. He was born on October 11, 1957, making him 33 years old during his first appearance and has been on Krusty's show from 1983-1990.
Sideshow Bob's defining feature is his curly, palm tree-shaped red hair (the palm-tree style has been used as visual gags in various episodes). His hair is exceedingly long when wet (as seen in Cape Feare), pulled or brushed. It tends to recoil and bounce back into shape with great ease. When he first appeared in The Telltale Head, he had an afro-like hairstyle, with a darker shade of red.
Sideshow Bob has various tattoos all over his body, some of which are against Bart.
- Chest: The words, "Die Bart, Die" (which he pretends in court is meant to be German for "The Bart, The")
- Back: Bart's Head (decapitated) on his skateboard with a speech bubble saying, "Ouch, Man!"
- Knuckles: "Luv" (right hand) and "Hāt" (left hand)
- ā is sometimes used as a long 'A' sound, so phonetically the above is pronounced 'Hate'
- Upper Left Arm: Skull and Crossbones
- Upper Right Arm: Knife
The tattoos have generally not been shown since, though it has not been confirmed if they have been removed or not.
Sideshow Bob, in a way, mirrors Hannibal Lecter; a psychopath who could recite Shakespeare by heart while stabbing you in yours.
Sideshow Bob enjoys the finer things in life, including reading classical literature and playing an instrument (a violin). 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. Despite his love of higher pleasures, he ironically hates the Ivy League school of Princeton University, which he disparagingly referred to as "Clown College" at least once. 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 thinks nothing of hurting others to get what he wants, even if this includes himself. 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 attempts at murdering Bart Simpson for foiling him. However, he has made several attempts at acquiring money and/or power, such as when he tried to kill Selma Bouvier or run a campaign for mayor as a republican (if for no other reason than to make the Simpsons miserable).
Despite his cold-blooded status, he does at times attempt to change. A notable instance was when he was released by Cecil and fully intended to change his past felon ways (even having reluctance at hurting Bart, his worst enemy). In addition, he also has some reserves, as when choosing to fashion a new life, he immediately rejects North Korea as a location for him to settle in. Similarly, the closest he ever came to killing Bart, he ended up saving him instead due to having second thoughts twice: The first time was when he brainwashed Bart into acting as a suicide bomber against Krusty as revenge (which he abandoned at the last minute after learning Krusty had regrets to his treatment over Bob during his time as his sideshow), and the second time was when preparing to tie Bart and Milhouse to a missile after he tricked the latter into exposing his location.
Largely because of his former status as a clown, he also was capable of extreme physical feats. For instance, he was able to contort his body to such an extent that he could easily fit into a package (which he implies was due to having to ride in Krusty's clown car cross-country). He also claimed that repeated blows from cream pies left his face immune to pain, short of self-inflicted surgeries as Bob learned the hard way. His face being immune to pain is somewhat implied with the rake gag, as he repeatedly gets hit by a rake in the face, yet only utters a growl of annoyance rather than actually appearing to be in pain. He was also adept at mimicking voices, particularly Krusty's, which he used to great effect when framing him.
Bob has a brother named Cecil, who is jealous of Bob for stealing his role during his audition for the Krusty the Klown Show, and tried to frame Bob for fraud. His parents are doctor, Robert Terwilliger Sr., and talented actress, Dame Judith Underdunk. After moving to Italy and becoming mayor of a small Italian village, Bob married a woman named Francesca (it is unconfirmed if they may be separated or divorced, as he is seen making plans to date an "age-appropriate woman" and flirting with Cassandra Patterson in Bobby, It's Cold Outside) and with her, had a son named Gino. When Homer must go to Italy to get Mr. Burns' new sports car, they just happen to stop in Bob's village. Bob tries to hide his past from his new wife but is unable, contrary to Bob's fear, his wife and son try and help him kill Bart.
Sideshow Bob declared himself an enemy of Krusty, as his role on the Krusty the Clown show was regularly cruel and demeaning. Since framing Krusty for armed robbery, Bob has attempted to kill him a couple of times. However, the last time Bob tries to, Krusty publicly confesses his regret for abusing him in his show by singing a nice song for him as an apology, which touches Bob so much. With that in line, they seemed to bury the hatchet. Despite this, he was seen holding a sign saying "Die Clown" when Krusty was drowning in a frozen lake in an attempt at baptism, and earlier had a sign in "Walt Warren's" house that said, "Kill Krusty, too!" (which is the only thing besides a reminder to buy milk that wasn't a message saying "Kill Bart") implying that Bob still has trace amounts of hatred towards Krusty.
Bart Simpson (temporarily friend)
He became Bart's nemesis after Bart figured out he had framed Krusty, getting him sent to prison. Ever since then, Bob has been obsessed with killing Bart, constantly plotting his revenge in prison. The first few times he was released from jail, Sideshow Bob would carry out a plan to murder Bart, or count it as a 'bonus' to one of his other schemes (the only three exceptions being when he successfully became Mayor, as he found it more fitting to just put Bart back in Kindergarten and demolish the Simpson house for the construction of "Matlock Highway" than to simply murder Bart [though he does warn that any Simpsons who remain at the house during the demolishment date will end up killed as a result], was released under the prison Christianity movement, where he attempted to atone for his sins, and most notably does not desire to even hurt Bart at all, and when Homer had disappeared from the third attempt at a wedding, where he interacted with Bart and Lisa in a manner that belied no hostility, and in fact also gave them a hint from the key-chain that the actual culprit was Selma and Patty Bouvier). Eventually, when he finally had Bart at his mercy, he lets him go as he has become "accustomed to his face". Strangely, Bob does not seem to hold any distinctive grudge against Lisa, despite the fact that she ruined his plans as mayor of Springfield, mayor of a small Italian village (unintentionally), and his attempt on the lives of her entire family (which even included her). This is possible because they have similar intellectual and cultural levels and, somehow, respect each other. He also does not hold a grudge against Marge, Homer or even Maggie, since he has no reason to hate them.
It is often implied that the real reason behind Bob's obsession with killing Bart is ego rather than to siege revenge on him for landing him in prison as he finds it infuriating that an underachieving 10-year old is constantly able to foil him with such ease.
The closest thing Bob has to a catchphrase comes from this relationship: Sometimes, Bob will reveal himself saying "Hello, Bart" in a menacing tone to which Bart (and sometimes Lisa and the rest of the Simpsons in unison) will exclaim "AH! Sideshow Bob!". However, in Gone Boy, Bob forces Milhouse to show them where Bart was located (being the only one who found the manhole Bart fell into). Predictably, he then shoves Milhouse down the manhole and prepares to use the military missile bunker's missiles to do away with his nemesis. However, he ultimately had a change of heart, and he and Bart accepted a truce and became friends. Bart was still wary of him, as depicted in Bobby, It's Cold Outside, where he was terrified upon learning that Sideshow Bob is the Santa's Village's main attraction, although Bob made clear that he had absolutely no intention of even harming Bart, let alone killing him (he claims its because his taking the part of Santa makes him compelled to stay in character as long as possible and thus cannot afford to act on his murderous urges, though his life goals folder that Bart discovered not even mentioning any harmful intentions towards the boy [or indeed, even mentions Bart at all] implies he genuinely stopped trying to act on his murderous impulses against Bart).
When Bob follows the Simpsons to their new home after they became a part of the Witness Protection Program, he clambers out from beneath their car, he steps on the end of a rake lying on the ground, causing it to fly up and hit him in the face and he shudders. He turns away from it, only for the same to happen, as another rake is lying nearby. It turns out that there are many rakes in this area, as the event repeats itself for some time. He is repeatedly the target of the rake slapstick gag, causing him to declare rakes as his greatest foe "besides Bart Simpson". In The Simpsons Game, when Bob steps on one rake and it flies up and hits him in the face, it knocks him out. Bob was attempting to murder Bart at Five Corners, (the only place in America where 5 states meet) Bart causes him to hop back and forth from state to state until he jumps on a rake which then hits him in the face. Most recently, Bob accidentally stepped on a rake underwater, after falling from atop Springfield Dam into the water below when he was "walking" away at the end of The Man Who Grew Too Much.
His occupation was to be Krusty's sidekick on the Krusty The Clown Show. He didn't even want the job: Bob accompanied his brother to the auditions and unwittingly impressed Krusty enough to be hired on the spot. His job before is unknown. He gave up on his sidekick job after he went to prison for framing Krusty, and has since become a master criminal, although the "master" part is spurious, as he has been repeatedly foiled by children. However, while being arrested the first time around, he warns the adults to not look down on children as they are more intelligent than they appear as "they were smart enough to get me!", implying that Bart and Lisa may have intelligence above most average kids.
In "Holidays of Future Passed", set 30 years after the regular series, it is implied that Bob has been murdered, as his chalk outline can be seen on the floor of Moe's Tavern, among other outlines, including the Capital City Goofball. It also could be implied that he accidentally killed himself from stepping on a rake, as there is also an outline of a rake next to his outline.
In "Gone Boy", a flash-forward scene at the end reveals that in the future he lives in a lighthouse regretting trying to get revenge since he wasted his life doing it, he tells this to Jeremy Freedman that life is short and not to waste it on revenge.
Sideshow Bob appears as the main antagonist of one segment of "Treehouse of Horror XXVI", entitled "Wanted: Dead Then Alive". In this story, Bob uses Milhouse's cellphone to text Bart and lure him into the music room alone after school. Once he has Bart cornered, he pulls out a harpoon gun and aims it at the boy. Bart is unfazed by the threat, certain that Bob will bungle his plan as usual. Bob responds by shooting him in the chest and killing him. Having finally succeeded in killing a 10-year-old child after 24 years, Bob sings with joy and changes his FiendBook status from "Attempted Murderer" to "Murderer".
Bob takes Bart's corpse home with him and amuses himself for several days desecrating the body. Once he grows bored with the dead boy, he decides to move into his "post-Bartum" phase and accepts a job as an associate professor at Springfield University. However, the school's standards are so low that simply reading the sign outside the entrance is the only requirement for acceptance, and Bob finds himself highly dissatisfied with the quality of his students (who spend most of his class looking up the answers to his questions online). Eventually, Bob comes to realize that he was happier when his life revolved around trying to kill Bart, so he decides to bring him back to life.
Using supplies he looted from the university's Engineering, Chemistry, and Occult departments, Bob constructs a machine that brings Bart back to life. Bob proceeds to repeatedly kill Bart, each time using his machine to bring him back to life so that he may be killed again. Eventually, Lisa sees Bart's dismembered body through Bob's basement window. She comments that she always suspected Bob was responsible for Bart's disappearance, even though Snake Jailbird had already been tried, found guilty and executed for the crime.
Lisa returns later with the rest of her family. They break into Bob's basement and use the machine to restore Bart to life. Bob walks in on them and pulls out a rifle to shoot them, but Homer hits him over the head with a lamp. Homer continues to beat Bob with the broken lamp until it decapitates him. Bart then takes Bob's head, along with a pair of deer antlers, frog legs, a wild boar's tail, the headless body of a chicken, and some of his own boogers for good measure, and uses the reanimation machine to bring Bob back to life as a horrible freaky creature. Afterward, Bob, as Creature Bob, returns to his job as a professor at Springfield University, but his students are too distracted by his appearance to learn anything.
He tries to kill the Simpson family once again during the opening sequence for Treehouse of Horror XXVII along with one of the Rigellians, the ghost of Frank Grimes and a Leprechaun. However, once again he fails, as Maggie decapitates all four of them, killing everyone but Frank's ghost (the latter only because, due to his obviously being dead already, he couldn't die again).
In the Simpsons/Family Guy crossover, Stewie Griffin captures and tortures Bart's enemies, one of them being Sideshow Bob.
Sideshow Bob appears as the main antagonist (although Kelsey Grammer refers to him as the ride's host) in The Simpsons Ride at the Universal Studios parks, in which he once again goes after Bart and the rest of the Simpson family.
The Simpsons Arcade game
Bob appears in Stage 5, The Springfield Butte. He carries a chicken in a food tray for the Simpsons to gain their health.
Bart vs. the Space Mutants
Bob was included as the boss of the Krustyland level in the 1991 video game Bart vs. the Space Mutants. He attacks by jumping around at Bart, and can only be defeated by stomping on his feet multiple times. If the player spelled Lisa's name earlier, she'll aid Bart by dropping bowling balls on Sideshow Bob's head, stunning him long enough for the player to land a clean hit on his feet. Oddly, he was primarily blue in this.
In The Simpsons Road Rage, there is a "Wanted" sign of Sideshow Bob in Evergreen Terrace. For some reason, he is named as "Sideshow" Bob Roberts. On it, he is wanted for 5,000 dollars.
Sideshow Bob appears at the end of Invasion of the Yokel-Snatchers to reveal himself as being in league with Kang and Kodos and prepares to do in Bart and Homer when he steps on a rake and knocks himself out.
Sideshow Bob appears in the game at random and the player has to catch him. If you are not quick he goes into hiding. Once you find Sideshow Bob, you get fifty-two dollars. You can also get him in the Terwilliger event.
Behind the Laughter
Sideshow Bob first appeared in the season one episode "The Telltale Head". In that appearance, his design was more simple and his hair was round in shape. However, towards the end of the episode, he appears again, in a panning shot of a crowd, with his familiar hairstyle. His first major appearance was in season one's penultimate episode "Krusty Gets Busted". Bob's design was updated for the episode, and the animators tried to redo his scenes in "The Telltale Head" with the re-design, but did not have enough time. Although, he was briefly seen in the mob with his normal hair.
For season three's "Black Widower", the writers decided to have Bob return to get revenge on Bart for foiling his plan in "Krusty Gets Busted". They took the idea of the Coyote chasing the Road Runner and had Bob always inserting himself into Bart's life. However, he did not appear in every season because the writers were not always able to think of reasons to bring Bob back, especially since Sideshow Bob episodes are written backward so they can work on the plotline. Another reason is that Kelsey Grammer is not a regular voice actor in the show.
The script for "Krusty Gets Busted" called for James Earl Jones to voice Bob, but the producers instead went with Cheers and Frasier actor Kelsey Grammer. Bob did not say anything during the first half of the episode, because the character always spoke with a slide whistle, and when he finally did speak, it would be a shock to hear Grammer's sophisticated, dulcet tones. Grammer used his impression of Ellis Rabb, a man that Grammer had once worked for, for Bob's voice.
Brad Bird first designed Bob for "Krusty Gets Busted". As the episode's animation progressed he made Bob sleeker, more urbane and refined, and worked with Grammer's voice. For "Black Widower", David Silverman updated the model to reflect the animation of Bird.
Despite common fan belief that Bob was named after the character Dr. Terwilliker from the film that Dr. Seuss wrote: The 5,000 Fingers of Dr. T, he was actually named after Terwilliger Boulevard in Portland, Oregon.
In twenty-one seasons of The Simpsons, Sideshow Bob has been heavily featured in ten episodes. Kelsey Grammer initially thought that Bob would be a one-time character, and calls him "the most popular character I've ever played." The writers believe that Grammer has a great voice and try to create something for him to sing in each episode he appears in. Grammer usually comes in for table readings, although when he cannot, Gregg Berger stands in for him. Former Executive producer David Mirkin found Grammer a joy to direct as he was very funny but noted that he hates doing the evil Sideshow Bob laughs. A rule for the early episodes that featured Bob was that there had to be a recap of his evil deeds in case the viewers did not remember them. The concept was dropped in later episodes or at least simplified.
Sideshow Bob's theme, which is used whenever Bob gets out of prison, was first used in the season three episode "Black Widower", Bob's second episode. It is based on the score of the movie Cape Fear, which was composed by Elmer Bernstein. The musical score for "Cape Feare" earned composer Alf Clausen an Emmy Award nomination for "Outstanding Dramatic Underscore - Series" in 1994. Bob's prisoner number is often 24601, which is Jean Valjean's prisoner number in Les Misérables. Another trademark for Bob is to step on rakes, a joke that first appeared in "Cape Feare". In that episode, Bob stepped on nine consecutive rakes, which the writers added to fill uptime. The sequence has become known as the "rake joke" and has been referred to as being "genius in its repetitive stupidity". His last name, Terwilliger, may have been taken from George J. Terwilliger III, a prominent Republican lawyer who served as United States Deputy Attorney General under George HW Bush.
Grammer recorded lines for Sideshow Bob for The Simpsons Movie, but the scene in which he was to appear was cut.
In a 2006 article, IGN.com ranked Bob in the second position on their list of the "Top 25 Simpsons Peripheral Characters", citing that he 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." Wizard Magazine rated Bob as the 66th greatest villain of all time.
WatchMojo placed Sideshow Bob as the 10th best Simpsons side character and the #1 Simpson villain, he surpassed Mr. Burns.
Kelsey Grammer has received praise for his voice work and in 2006, he won the Primetime Emmy Award for Outstanding Voice-Over Performance for his performance as Bob in the episode "The Italian Bob". Grammer had previously won four in the Outstanding Lead Actor in a Comedy Series category for his portrayal of Frasier Crane on Frasier. In a 2007 interview, Simpsons executive producer Al Jean listed Grammer as his second favorite guest star, saying "his voice is so rich". Mike Bruno of Entertainment Weekly called Kelsey Grammer one of "fourteen guest stars whose standout performances on TV make us wish they'd turn up in a Simpsons Movie 2". David Hyde Pierce was also included in that list. Ben Rayner of the Toronto Star listed "Cape Feare", "Sideshow Bob's Last Gleaming" and "Brother from Another Series" as being among the best episodes of the series, saying "Forget Frasier, these are Kelsey Grammer's best roles."
The production staff on The Simpsons are usually excited about "Sideshow Bob episodes" as the writers consider them a treat to write, and the directors think they are always crazy and fun for them to animate.
Many episodes featuring Bob have been well received by fans and critics. "Cape Feare", the third episode to feature Sideshow Bob, is generally regarded as one of the best episodes of The Simpsons, and according to Matt Groening, people often include it among their top 10 favorites. In Entertainment Weekly's top 25 The Simpsons episodes ever, it was placed third. In 2006, IGN.com named Cape Feare the best episode of the fifth season. Vanity Fair called it the show's fourth-best episode in 2007, as "this episode's masterful integration of film parody and a recurring character puts it near the top." Associated Content chose the score for this episode to be 11th place of all of The Simpsons episodes. Grammer's performance of H.M.S. Pinafore was later included on the album Go Simpsonic with The Simpsons. The season 17 episode "The Italian Bob" and its writer John Frink would win a Writers Guild of America Award in 2007 in the animation category.
Bob was made into an action figure, and two different versions were included as part of the World of Springfield toy line. The first shows Bob as he was on The Krusty the Clown Show, and was released in 2001 as part of the Krustylu Studios wave three playset. The second, released in 2002, has him in the prison uniform he wore in "Sideshow Bob's Last Gleaming", and was a part of wave nine. He was also made into a collectable Funko Pop! figure, being part of wave 3 of their Simpsons series.
- Bob's prisoner number is 24601, like Seymour Skinner's POW number, in reference to Jean Valjean's prisoner number in Les Misérables. However in Sideshow Bob's Last Gleaming his prison number is A-113, another referenced number in the series.
- In The Simpsons Road Rage, there is a "Wanted" sign of Sideshow Bob in Evergreen Terrace. For some reason, he is named as "Sideshow" Bob Roberts, perhaps as a nod to the episode of the same name from season six.
- Bob's Wanted sign also appears in the background of Chief Wiggum's station in Treehouse of Horror V.
- Bob shares many similarities with the character Frasier Crane, from Cheers, and later Frasier, from voice to taste. In fact, in "The Bob Next Door", when the Simpsons gain a neighbor who sounds remarkably like Sideshow Bob, Marge cites Frasier to a panicked Bart, saying a "lot of people sound like Sideshow Bob". Kelsey Grammer plays both Frasier and Bob, except in "Krusty Gets Busted", where Kelsey still mostly voiced Bob but shared lines with series regular Dan Castellaneta.
- Bob's brother Cecil and their father Robert Terwilliger Sr. were played by David Hyde Pierce and the late John Mahoney respectively, echoing the roles they played on Frasier as Frasier's brother Niles and their father Martin. Additionally, the arguments between Bob and Cecil in "Brother from Another Series" are a homage to the arguments between Frasier and Niles in Frasier.
- In The Simpsons Arcade, he only appears in stage 5 and helped the Simpsons fight Mr. Burns' goons by giving them food which he was carrying in a food tray.
- Sideshow Bob never appeard in The Simpsons Movie. However, Kelsey Grammer voiced him in a deleted scene.
- Treehouse of Horror XXVI marks his first appearance in a Treehouse of Horror episode.
- He is the featured character on the Season 17 DVD/Blu-ray box set.
- In "Black Widower", Sideshow Bob is Buddhist.
|The Simpsons: Season Three|
|"Stark Raving Dad":||"Mr. Lisa Goes to Washington":||"When Flanders Failed":||"Bart the Murderer":||"Homer Defined":|
|"Like Father, Like Clown":||"Treehouse of Horror II":||"Lisa's Pony":||"Saturdays of Thunder":||"Flaming Moe's":|
|"Burns Verkaufen der Kraftwerk":||"I Married Marge":||"Radio Bart":||"Lisa the Greek":||"Homer Alone":|
|"Bart the Lover":||"Homer at the Bat":||"Separate Vocations":||"Dog of Death":||"Colonel Homer":|
|"Black Widower":||"The Otto Show":||"Bart's Friend Falls in Love":||"Brother, Can You Spare Two Dimes?":|
|The Simpsons: Season Four|
|"Kamp Krusty":||"A Streetcar Named Marge":||"Homer the Heretic":||"Lisa the Beauty Queen":||"Treehouse of Horror III":|
|"Itchy & Scratchy: The Movie":||"Marge Gets a Job":||"New Kid on the Block":||"Mr. Plow":||"Lisa's First Word":|
|"Homer's Triple Bypass":||"Marge vs. the Monorail":||"Selma's Choice":||"Brother from the Same Planet":||"I Love Lisa":|
|"Duffless":||"Last Exit to Springfield":||"So It's Come to This: A Simpsons Clip Show":||"The Front":||"Whacking Day":|
|"Marge in Chains":||"Krusty Gets Kancelled":|
- "Cape Feare"
- "The Bob Next Door"
- "Sideshow Bob Roberts"
- "The Italian Bob"
- "Funeral for a Fiend"
- Lisa's First Word
- Brother from Another Series
- Krusty Gets Busted
- Black Widower
- Cape Feare
- Sideshow Bob Roberts
- Sideshow Bob's Last Gleaming
- Day of the Jackanapes
- Pokey Mom
- The Great Louse Detective
- The Italian Bob
- Wedding for Disaster
- American History X-cellent
- The Bob Next Door
- At Long Last Leave
- Moonshine River
- Gone Abie Gone
- The Man Who Grew Too Much
- Clown in the Dumps
- The Simpsons Guy
- Blazed and Confused
- Gone Boy
- Bobby, It's Cold Outside
- Funeral for a Fiend
- The Man Who Grew Too Much
|Robert Terwilliger Sr. | Dame Judith Underdunk | Sideshow Bob | Cecil Terwilliger | Francesca Terwilliger | Gino Terwilliger|