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Hello, Bart.
~ Sideshow Bob's catchphrase.
Treat kids as equal! They're people too! They're smarter than you think! They were smart enough to catch me!
~ Sideshow Bob upon exposed before being taken away to jail the first time.
Well, Krusty as you may remember, after I tried to frame you for armed robbery, I tried to murder Selma Bouvier. Let's see, I rigged the mayoral elections, I tried to blow up Springfield with a nuclear device and I tried to kill you. [...] And whenever I could find a spare moment, I've tried to murder Bart Simpson.
~ Sideshow Bob.

Dr. Robert Underdunk “Sideshow Bob” Terwilliger Jr. is the secondary antagonist of The Simpsons franchise.

He is a former television personality on The Krusty the Clown Show turned criminal mastermind. He is primarily the arch-nemesis of Bart Simpson and Krusty the Clown, as he desires to kill them both, the former for foiling his schemes and the latter for constantly abusing him in the show. He doesn't want to just go after Bart, he wants to go after the rest of the Simpson family and kill them, as well. In fact, he considers Lisa Simpson his second arch-nemesis due to the parts that she often plays in the foiling of his schemes.

He has constantly come up with multiple evil plans, such as framing Krusty for robbery, hunting down Bart and attempting to become mayor and continues to serve as an attempted murderer and a criminal.

He is voiced by Kelsey Grammer, who also played Stinky Pete in Toy Story 2, Rothbart in Barbie of Swan Lake, Harold Attinger in Transformers: Age of Extinction and Hunter in Storks.

History[]

Sideshow Bob started out as the mute sidekick of children's show host Krusty the Clown. Bob abusively went through an act that involved being shot out of a cannon by Krusty himself, all the while being deemed hilarious to the child audience.

Finally having enough, Sideshow Bob disguised himself as Krusty and robbed the Kwik-E-Mart and framed him, resulting in the clown being arrested and Bob being made the new host of his show. The only main character who witnesses the act in the Kwik-E-Mart was Homer Simpson.

However, Bob's victory was to be short lived. Not long after the robbery, Bob began shooting an interview on Krusty's condition with Bart Simpson, Homer's son. As Bob began a speech on Krusty's 'behalf', it was then that the pieces of the puzzle finally connected in Bart's brain, slowly figuring out that Sideshow Bob was behind the robbery all the time and that he framed Krusty for it. The young Simpson then exposed Bob to the authorities and had him arrested.

This was not the end, however, as Sideshow Bob swore revenge on Bart as he was taken away, beginning what would be a decades-long run as the boy's archnemesis.

Rivalry with Bart[]

See Sideshow Bob/Synopsis

Personality[]

Sideshow Bob is a complex character in the series. He is a sadistically obsessed psychopath by trying to kill Bart Simpson, yet he is often very smart and sophisticated in talk, and has shown redeeming qualities in the past such as deciding against killing Krusty when he realized that he regretted mistreating him (which led to his start to villainy). He also doesn't want to kill only Bart, he wants to kill the Simpson family. His main target besides Bart is his sister, Lisa (especially in more recent seasons when he has repeatedly targeted both children).

Sideshow Bob enjoys the finer things in life, including reading classical literature, and possesses a massive intellect. Likely due to his upbringing, he has a passion for theater, knowing Gilbert and Sullivan's H.M.S. Pinafore 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 the time when he was a master criminal, he studied the uses of dynamite, which would theoretically be considered low-class. At times, he also seems to possess genuine desires to help humanity, as he explains that his motivation for rigging the mayoral election for Springfield was to "save them from themselves" (and based on the city's collective brain trust, he might not necessarily have been wrong).

In addition, when he briefly took over Krusty's show after framing the latter for armed robbery, Bob then attempted to insert more high culture into the show (i.e. reading to the child viewers from the classic novel The Man in the Iron Mask) in an attempt to encourage children's intellectual development, and his plot to threaten Springfield with a nuclear bomb unless they abolished television was done because he saw just what a negative, mind-numbing effect television can have on people and thus believed that forcing the people of Springfield to abolish it would be greatly beneficial to them in the long run.

Along those lines, in an interview with the "Star Wars Insider" magazine, a couple of the Simpsons producers were asked if there were any Springfield characters who disliked Star Wars. One of them initially said Sideshow Bob, but the other corrected him that Bob would very much appreciate that Star Wars contains themes on the importance of young people going out into the world and making something of themselves.

Beneath the cultured gentlemen, however, is still the heart of a cold-blooded killer. Bob is a prejudicial man who is willing to hurt others to get what he wants. His primary motive seems to be revenge. His original crime, framing Krusty, was an attempt to get back at him for making a clumsy fool of him for years as his sidekick, and most of his other crimes have been more evil attempts pedicide by nearly killing Bart Simpson (and, at times, Lisa Simpson, as well) 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, but Bart still stopped him, anyway, since he and Selma are still family), or even run a campaign for mayor as a Republican (if for no other reason than to make the Simpsons miserable).

Relationships[]

Family:[]

  • Wife: Francesca Terwilliger
  • Parents: Robert Terwilliger, Sr. and Judith Terwilliger
  • Brother: Cecil Terwilliger
  • Son: Gino Terwilliger
  • Nephew: Neil Terwilliger
  • Cousin: Bobby Terwilliger

Allies:[]

Enemies:[]

  • Bart Simpson - Archenemy
  • Krusty the Clown - Second Archenemy
  • Selma Bouvier - Attempted victim
  • Marge Simpson - Attempted victim
  • Homer Simpson
  • Russ Cargill
  • Lisa Simpson
  • Count Dracula
  • Frankenstein
  • Invisible Man
  • Bride of Frankenstein
  • Mummy
  • Gil-Man
  • Werewolf
  • Metaluna Monster

Appearance[]

Bob is a tall, slim man who is easily recognized for his pale skin, abnormally large feet and his thick, red palm-tree shaped hair that springs out of his head. When not in jail and wearing the standard orange prison jumpsuit and brown shoes of Springfield Penitentiary inmates Bob usually has a rather casual but still smart sense of fashion. When he was Krusty's sideshow he was shirtless and wore a grass skirt and red clown shoes and as a mayor he wore a stone grey suit with a red tie and light blue shirt with brown shoes.

In other media[]

  • Bob also has a brief cameo appearance 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 was the main antagonist on the ride at Universal Studios called 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 he also allows them to pick another group to come with them, which Bart chooses to be the riders. Sideshow Bob laughs 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 riders) while they crash through different parts of Krustyland. He first tries sabotaging the track on the initial ride by destroying it with a wrecking ball. Then, he dons a giant panda costume and attempts to kill Bart and Lisa while they are on a Happy Little Elves ride. He then goes after Homer and Marge by sending them through a lazy river ride laced with "temptations" that could kill them if taken (which Homer falls for by taking a gigantic mug of beer, which causes a chain reaction of accidents that almost kill him and Marge). But at the end of the ride, Sideshow Bob gets crushed by the Simpsons' couch when the family fell down the death drop. It is unknown what happened to him after that, but it is probable that he was then caught and arrested for his villainous actions and sent back to jail.
  • Bob is a supporting antagonist in The Simpsons Game where he works for Kang and Kodos.

Quotes[]

Hand over all the money in a paper bag!
~ Sideshow Bob mimicking Krusty while robbing the Kwik-e-Mart
My young friends, for years, I have been silent, save for the crude glissando of this primitive wild instrument. But now, destiny has thrust me into the center ring.
~ Sideshow Bob's first lines after framing Krusty.
Ow! My foot, you lousy stupid clumsy..
~ Sideshow Bob getting his foot hurt.
(Groan)
~ Sideshow Bob stepping on a rake.
Very well, Bart, I will send you to heaven, before I'll send you to Hell!
~ Sideshow Bob agreeing to Bart's "final request"
And now.. The final curtain!
~ Sideshow Bob preparing to kill Bart.
By Lucifer's beard!
~ Sideshow Bob in vein after the Simpsons' boat returns to Springfield
Oh, that was a big mistake, Bart. No children have ever meddled with the Republican Party and lived to tell about it.
~ Sideshow Bob to a Bart trying to sabotage his mayoral bid.
You can't handle the truth! No truth-handler, you. BAH! I deride your truth-handling abilities.
~ Sideshow Bob.
I'll Stay away from your son alright.. stay away, Forever.
~ Sideshow Bob threatening remark Against Bart to Marge Simpson.
Then let's give the people..WHAT THEY WANT!
~ Sideshow Bob shoving Bart in his own coffin in an attempt to cremate him.
Bob: Rakes.. my old archenemy

Bart: I thought I was your archenemy?
Bob: I have a life outside, Bart.

~ Sideshow Bob upon stepping at yet another rake
Poor Selma, we were having such a lovely evening.♪And then I go and spoil it all by doing something stupid, like explode you.♪
~ Sideshow Bob after supposedly having killed Patty Selma.
I'll be back, you can't keep the Democrats out of the White House forever, and when they get in, I'll be Back on the Streets with all my criminal buddies! *Maniacal Laughter*
~ Sideshow Bob after yet another failed scheme by Bart.
The deed is done. Twenty four years, trying to kill a 10-year old has finally payed off...
~ Sideshow Bob after successfully killing his nemesis in the Treehouse of Horror episode "Wanted: Dead, Then Alive."
Simpson Family, I hear-by swear. Vendetta!
~ Sideshow Bob swore to eradicate the Simpsons after his identity is tarnished in Venice
I've grown accustomed to you.
~ Sideshow Bob to Bart after hesitating to kill him.
Die, Krusty, Die!
~ Sideshow Bob dramatically trying to ram the stolen Wright Flyer towards Krusty.
I agree.
~ Sideshow Bob without a second thought trying to detonate a Nuke upon failing to do so after Lisa's remarks.
Television, how I loathe that box, that omni-directional sludge pup drowning and burping-
~ Sideshow Bob's views on television
Hello, Springfield, sorry to divert your attention from all the big noises and shiny things, but something's been troubling me. Television. Wouldn't our lives be so much richer when television was done away with? Why we could revive the arts of conversation, and scrimshaw! Thus I submit to you. We abolish television. Permanently. Oh, and one more thing. I've stolen a Nuclear Bomb, if you do not rid this city of television within Two Hours I will detonate it. Farewell.
~ Sideshow Bob threatening Springfield while ranting about his worldly views.
Kill Bart!! KILL BART!!! (Moe: Actually, we're just killing Homer.) Oh.
~ Sideshow Bob's lines in a deleted scene of The Simpsons Movie when he joins up the angry townspeople as he believes that they want to kill Bart, only to be reminded by Moe that they actually want to kill Homer instead.
And now the last thing you’ll ever see: a legally required safety video.
~ Sideshow Bob before a itchy and scratchy safety video in The Simpsons Ride

Trivia[]

  • James Earl Jones was originally cast as Bob before the producers chose to have Kelsey Grammer voice the character instead.
  • Despite not appearing in The Simpsons Movie, Kelsey Grammer voiced Bob in a deleted scene that is still unreleased for unknown reasons. According to the deleted scene, Bob is among the angry townspeople heading towards the Simpson residence, assuming that they want to kill Bart for polluting the lake and having the town sealed in a dome by the EPA (led by Russ Cargill). However, Moe points out to Bob that the townspeople actually want to kill Homer instead as the latter is revealed to the true culprit, and that Bart has nothing to do with it. Upon hearing this, Bob leaves in disappointment.
  • In "The Telltale Head", Sideshow Bob's earlier design sports an Afro and a big rounded nose.
  • There is a notable recurring gag where Bob accidentally steps on a rake due to his big feet.
    • Bob even view rakes as his archenemies aside from Bart.
  • Despite having his plan of usurping Krusty's show foiled by Bart, his plot initially worked when he received positive reviews and a reward for best TV Personality given to him in prison.

External Links[]

Navigation[]

               The Simpsons Logo Villains

Springfield Republican Party
Birch Barlow | Lindsey Naegle | Count Dracula | Blue-Haired Lawyer | Waylon Smithers

Terwilliger Family
Cecil Terwilliger | Dame Judith Underdunk | Francesca Terwilliger | Gino Terwilliger | Robert Terwilliger, Jr. | Robert Terwilliger, Sr.

Springfield Mafia
Fat Tony | Fit Tony | Johnny Tightlips | Legs | Louie | Don Vittorio D'Maggio | Frankie the Squealer | Johnny the Snitch | Ned Flanders Sr. | Nicky Bluepants Altosaxophony | Joey | Dante Calabresi Sr. | Dante Calabresi Jr. | Primo | Shotgun Pete

Burns Family
Mr. Burns | Clifford Burns | Wainwright Montgomery Burns | Ironfist Burns

Recurring Characters
Agnes Skinner | Artie Ziff | Baby Gerald | Clancy Wiggum | Constance Harm | Dolph Starbeam | Gina Vendetti | God | Hans Sprungfeld | Herman Hermann | Itchy | Jessica Lovejoy | Jimbo Jones | Jack the Ripper | Kearney Zzyzwicz | Mayor Quimby | Mr. Largo | Patty & Selma Bouvier | Rich Texan | Senator Mendoza | Shauna Chalmers | Snake Jailbird | Space Mutants

Treehouse of Horror
Homer Simpson: III | V | XXII | XIV | XIX | XVIII | XXV | XXVII | XXXIV | The Blob | The Fat in the Hat | Homerzilla | Homer's Clones

Marge Simpson: Witch Marge | XVIII

Bart Simpson: The Raven | II | IV | VII | XVI | XX | XXV | XXXI | XXXII

Lisa Simpson: XXIX | XXXIII | XXXIV

Maggie Simpson: IX | XXX | XXXIV

Mr. Burns: II | XVI | XXVII | XXXI | XXXIII | XXXV | Count Burns | Burnsiverse | Lord Montymort

Waylon Smithers: II | Slithers

Moe Szyslak: XX | Moe-Looking Satan | V | XXV

Sideshow Bob: XXVI | XXXIV

Others: Bart (Fly) | Zombies | Gremlin | Groundskeeper Willie | Jonathan Frink Sr. | Kang and Kodos | Killer Toupée | King Snorky | Killer Krusty Doll | Lard Lad | Muttonchop Murderer | French President | Ned Flanders | Seymour Skinner | Doris Freedman | Edna Krabappel | The Devil | Dr. Julius Hibbert | Billy the Kid | The Grand Pumpkin | The Mutants | Witch Patty & Selma | Rachel | Munchers | Death | The Pookadook | Metaluna Mutant | Steve Johnson | The Collector | Universal Monsters | Ultrahouse 3000 | Pazuzu | The Other Simpsons Family | Bart's Toys | Krusto D. Clown | Lenny Leonard | Carl Carlson | Bad Dream House | Count Dracula | Itchy and Scratchy | Artie Ziff | Snake Jailbird | Jelly Monster | Clancy Wiggum | Gary Chalmers | Mopey Mary | Gypsy | Bart's Treehouse | Political Monsters | Denim | Springfield Fire Department | Luann Van Houten

Other Characters
Adil Hoxha | Adolf Hitler | Andy Hamilton | Baby Button Eyes | Bart Simpson's Creatures | Beautiful Bart | Blue-Eyed Man | Bob Arnold | Captain Mordecai Barrows | Cesar & Ugolín | Chett Englebrick | Clownface | Cooder | Comic Book Guy (Brick Like Me) | Devan & Quenley Woosterfield | Dexter Colt | Dwight Diddlehopper | Environmental Protection Agency (Russ Cargill) | Frank Grimes, Jr. | Francine Rhenquist | French Chef | George H.W. Bush | Glamorous Godfrey | Globex Corporation (Hank Scorpio, Miss Goodthighs) | Hell's Satan | Homer Gimplet | Howard K. Duff VIII | Hypnotoad | Itchy & Scratchy Bots | Jack Crowley | Jack Lassen | Jay G | Joan Bushwell | The Jockeys | Julia | Kostas Becker | Larry Kidkill | Lucille Botzcowski | Lyle Lanley | Les Moore | Jim Hope | Mayor of Albuquerque | Mav & Portia | Michael De Graaf | Molloy | Movementarians | Mr. Dirt | Ms. Cantwell | Ms. Kelp | Nigel Bakerbutcher | Officer Krackney | Pa MacWeldon | Professor Werner Von Brawn | Rex Banner | Robotic Richard Simmons | Rover | Siegfried Blaze | Shadow Knight | Sparklemon | Stanley DeGroot | Stonecutters (Homer Gimplet)| The Leader | William Shakespeare | Paolo Paoletti

Guest Star Characters
Will Wright | Taika Waititi

Video Games
Simpsons Arcade
Mr. Burns | Mr. Smithers | Hench Dogs | Robot Burns

The Simpsons: Hit and Run
Agnes Skinner | Kang and Kodos | Mr. Burns | Patty and Selma Bouvier | Snake Jailbird | Springfield Mafia (Fat Tony & Louie) | Wasp Cameras | Waylon Smithers | Zombies

The Simpsons Game
Matt Groening | Kang and Kodos | Chocolate Rabbits (White Chocolate Rabbit) | Security Guards (The Simpsons Game) | Riot Cops | Tree Loggers | Jimbo Jones | Dolph Starbeam | Kearney Zzyzwicz | EA Executive | Stubborn Ape | King Snorky | Lard Lad | Mr. Burns | Waylon Smithers | Sideshow Bob | Selmatty | Itchy | God

The Simpsons: Tapped Out
Mr. Burns | Russ Cargill | Frankie the Squealer | Sven Holly | Evil Homer | Bandits | Count Dracula | Rich Texan | Fernando Vidal | Grampasaurus | Itchy & Scratchy Bots

See Also
Futurama Villains | Disenchantment Villains

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