Robert Terwilliger


 * For Sideshow Bob's father, see Robert Terwilliger Sr..
 * For other uses, see Sideshow Bob (disambiguation).

"Hello, Bart."

- Sideshow Bob

Dr. Robert "Bob" Underdunk Terwilliger, Jr., better known by his stage name, Sideshow Bob, which he got when he was Krusty the Clown's sidekick. 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 Gilbert and Sullivan operettas and is known for his huge feet, which have gotten him into trouble on more than one occasion.

Biography
Robert Terwilliger began his career as "Sideshow Bob", a non-speaking sidekick on Krusty the Clown's television show. In actuality his younger brother Cecil had auditioned for the role, which Krusty was not impressed by and saw Bob as the ideal comic foil. Sideshow Bob endured much as was to be expected from 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 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 of 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 comitting 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 comitting 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. After he was released from prison, he proposed and married Selma, despite Bart's protests. As part of a scheme to inherit money she has invested in the stock market, Bob attempted to blow Selma up 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'd 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 letter 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 some problems with his health 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. The delaying tactic lead 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 defeated liberal incumbent Joe Quimby in a landslide, and 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, leading to another incarceration.

During his prison sentence, he began to develop a growing dislike of television, calling it "a fountain of mindless drivel". 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 disguised as an officer, where he found 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 smarting 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.

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 and brainwashes 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.

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 and Lisa. To keep him from trying to commit crimes, 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 not reveal his felonious past; however, a drunken Lisa jokes about Bob's criminal deeds, alienating Bob 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 temporarily 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 save 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 thinking he was prepped up to kill Homer Simpson (Homer went missing at Marge's third wedding and thought Sideshow Bob was the culprit due to a clue, keys 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 keychain, 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.

Bob also has a brief cameo in the Simpsons/Family Guy crossover episode, as one of many of Bart's enemies that Stewie Griffin kidnaps and tortures.

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.

Comics
Sideshow Bob has appeared in many Simpsons Comics. In one, for example, 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 wont 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.

He makes a minor cameo in issue 208, 'Brit Simpson', on page 11 as Sideshow Bobby.

Appearance
He has unusually large feet (they actually fill his oversized 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.

Hair
Sideshow Bob's defining feature is his curly, palm tree shaped red hair (the palmaceae 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 tents to recoil and bounce back into shape with great ease.

Tattoos
Sideshow Bob has various tattoos all over his body:
 * 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!"Cape Feare.png
 * Knuckles: "Luv" (right hand) and "Hāt" (left hand)
 * ā is sometimes used as a long 'A' sound, so phoenetically the above is pronounced 'Hate' 
 * Upper Left Arm: Skull & 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.

Personality
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. Likely due to his upbringing, he has a passion for theatre, 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 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)

Family
Bob has a brother named Cecil, whom 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 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.

Krusty the Clown
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 a singing a nice song for him as an apology, which touches Bob so much. With that in line, they seemed to bury the hatchet.

Bart Simpson
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 two exceptions being when he 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 keychain 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 the she is often the one who foils his schemes instead of Bart. This is possibly because they have similar intellectual and cultural levels and, somehow, respect each other.

It is often implied that real reason behind Bob's obsession with Killing Bart is Ego rather than revenge, As he finds it infuriating that an underachieving 10-year old is constantly able to foil him.

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, in unison) will exclaim "Ahhh! Sideshow Bob!".

Rakes
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.

Career
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 "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.



Flash-Forward
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.

Ride
Sideshow Bob appears as the main antagonist in The Simpsons Ride at the Universal Studios parks, in which he once again goes after the Simpson family.

Sideshow Bob also appears as a new mascot along with Krusty as part of an expansion at Universal Studios in Florida.

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 a level boss in the 1991 video game Bart vs. the Space Mutants.

The Simpsons Road Rage
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 5000 dollars.

The Simpsons Game
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.

The Simpsons: Tapped 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.

Creation
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.

Voice
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 voice. Grammer used his impression of Ellis Rabb, a man that Grammer had once worked for, for Bob's voice.

Appearance
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.

Name
Despite common fan belief that Bob was named after the character Dr. Terwilliker from the film that wrote: The 5,000 Fingers of Dr. T, he was actually named after Terwilliger Boulevard in Portland, Oregon.

Development
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 up time. The sequence has become known as the "rake joke" and has been referred to as being "genius in its repetitive stupidity".

Grammer recorded lines for Sideshow Bob for The Simpsons Movie, but the scene in which he was to appear was cut.

Reception
In a 2006 article, IGN.com ranked Bob in 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.

Kelsey Grammer has received praise for his voicework 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 filmic parody and a recurring character puts it near the top."[30] 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.

Cultural influence
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 play set". 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".

Trivia

 * 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 shares many similarities with the character Frasier Crane, from Cheers, and later Frasier, from voice to tastes. 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 Grammar 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 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 a food which he was carrying in a food tray.
 * His prison number is "A113", a reference to the number found in Pixar movies.