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Characters / The Simpsons - Government, Judges, Lawyers, Police, Criminals

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Government

    Mayor Joe Quimby 
https://static.tvtropes.org/pmwiki/pub/images/mayor_quimby.png

Debut: "The Call of the Simpsons"

Springfield's mayor and head of a rich and politically influential clan. Known for his womanizing, general corruption and for changing his political stance at the drop of a hat if he thinks it will increase his popularity with the voters. Voiced by Dan Castellaneta.


  • The Alcoholic: In Italy, his picture illustrates "Drinko Drivo".
  • Catch-Phrase: "Vote Quimby!"
  • Corrupt Politician: A massively over-the-top example. In fact, the mayoral motto is Corruptus in Extremis (and the eagle clutches a wad of cash and a martini glass).
  • Everyone Has Standards:
    • Despite his ways, he does have his limits like having a woman thrown in jail for her nervous breakdown note , and holding the town hostage for monetary reasons note .
    • Though a huge womanizer, he was horrified at the idea of sleeping with his niece.
    • In "A Star Is Burns", he bemoans the fact the town is full of, in his own words, "ignorant rednecks" that do things like try to burn Principal Skinner at the stake for saying the Earth moves around the Sun.
  • Fat Idiot: Though nowhere near as bad as Homer or Chief Wiggum.
  • Future Loser: Has lost his lofty political position and become a taxi driver in the hypothetical future episode "Lisa's Wedding".
  • I Take Offense to That Last One!: Diamond Joe would have you know that though he is a tax-cheat, a wife-swapper, and a pot-smoker (and grower, since he has a marijuana plant in his office closet that he tends to every day), he is no longer illiterate.
  • Kavorka Man: He is the mayor. What he looks like doesn't matter much.
  • Mayor Pain: Trope Namer for Type B. An outright corrupt, opportunistic, embarrassing, sleazy politician who couldn't care less for Springfield.
  • My God, What Have I Done?: When his secret flirt reminds him she is indeed his niece he is both shocked and disgusted with himself.
  • Noble Demon: He blatantly violated the law by getting Marge released without charges after she blocked a bridge with her car, and did it for purely selfish reasons, but after everything Marge went through she arguably didn't deserve to go to jail.
  • No Celebrities Were Harmed: The Quimby clan displays many of the hallmarks of the seamier sides of the Kennedys, although Diamond Joe in some stories also resembles other Democratic politicians, most notably former Massachusetts governor Michael Dukakis in "Sideshow Bob Roberts"note . Mrs. Quimby dresses like Jacqueline Kennedy.
  • Overly Long Name: Joseph Fitzgerald O'Malley Fitzpatrick O'Donnell the Edge "Diamond Joe" Quimby
  • Pet the Dog: He was willing to sacrifice television if it meant stopping Sideshow Bob from detonating a nuke.
  • Really Gets Around: Some are escorts, others are mistresses.
  • Sleazy Politician: In fact, he provides the page image of this trope.
    • He has constant extra-marital affairs, takes bribes, dodges taxes and embezzles city funds. During an outbreak of the flu, he flees to a Caribbean island and mocks the beach up as his office saying that he won't leave the city and also goes on a "fact-finding mission" to Aruba, where he determines that a supertrain directly connecting it with Springfield is unfeasible.
    • A darker side of this is revealed in "Krusty Gets Kancelled" when he openly admits to having had his political opponents killed and dumped in the Springfield harbor.
  • Screw the Rules, I Have Connections!: When Marge suffers a nervous breakdown and blocks traffic on a bridge, she is arrested. Mayor Quimby immediately pulls some strings to get her released without charges, claiming that if she went to jail, he could kiss the "chick vote" goodbye. He points out that if he wanted all the laws and rules to be respected he wouldn't have put Wiggum in charge.
  • Screw the Rules, I Have Money!: When his nephew Freddy was Wrongly Accused of beating a French waiter half to death, Mayor Quimby began bribing witnesses to testify on Freddy's behalf. It didn't work, however, because of Freddy's Hair-Trigger Temper.
  • The Stoner: Smokes pot, and even grows several plants in his office.
  • Strawman Political: As the series' most prominent recurring Democratic politician, he serves as the primary target for Take Thats aimed at Democrats and liberals.
  • Verbal Tic: He always begins his sentences with "Er um uh". Even his offspring has this verbal tic (see below). Lampshaded when Homer plans to use Bart to take advantage of the situation, and Bart uses this verbal tic to trick Quimby into thinking he's his son.
  • Vitriolic Best Buds: He has a strained friendship with Chief Wiggum, as the two men vie to have control over the city, which once lead to a serious argument in regards of who takes over during an emergency on the Monorail crisis.
  • Your Cheating Heart: Has a wife, but has had several gazillion different mistresses throughout the series (one of which is a squawky-voiced beauty queen for whom he bought an opera house, like Charles Foster Kane did for his mistress, whose singing voice was good, but not good enough for opera).

Judges and Lawyers

    Judge Roy Snyder 
https://static.tvtropes.org/pmwiki/pub/images/roy_snyder_official_image.png
Debut: "Krusty Gets Busted"

One of the main judges in Springfield. Voiced by Harry Shearer.


  • Ambiguously Brown: His skin color has changed from yellow to brown repeatedly throughout the series before staying brown.
  • Bunny-Ears Lawyer: A good judge for the most part, but has a strange preoccupation with a clown desk figurine.
  • First-Name Basis: With Bart, to show that he is familiar with the delinquent. Bart would have been sent to juvie if Snyder wasn't that lenient toward him.
  • Reasonable Authority Figure: One of the few people with authority in Springfield who is (usually) characterised as competent, non-brutal, and non-corrupt.
  • Your Cheating Heart: He admitted in court that his wife had left him, since then he has been seen with Lindsey Naegle.

    Judge Constance Harm 
https://static.tvtropes.org/pmwiki/pub/images/2054878_judge_constance_harm.png
Debut: "The Parent Rap"

Voiced by Jane Kaczmarek.


  • Cool Pet: Has a pet seal named Poncho that doubles as a guard dog, and barks like one.
  • Disproportionate Retribution: A lot. One example would be in "On a Clear Day, I Can't See My Sister", when she increases the distance on how far Bart has to be from Lisa after Bart insults her.
  • Hanging Judge: To give one example of how harsh she can be, in one episode she retracted Homer's driving license for driving his car off a dock (because it had too many accessories installed) doing so by cutting up the license, chopping the pieces up with a miniature guillotine, feeding what was left to a pair of dogs, and then ordering the court officers to "Burn their poop!". She also allowed Lisa (a minor with no consent from her parents) to file a restraining order on her own brother and increased the order's range when Bart (stupidly) insulted her figure during the appeal.
  • Jerkass: Big time. It doesn't help that she's played by Jane Kaczmarek. She enjoys creating cruel and unusual punishments for criminals in her court.
  • Jerkass Has a Point: Despite being a harsh jerkass, she does rightfully call out Homer for being a bad father.
  • Pet the Dog: In the 300th episode she does grants Bart emancipation from his family, specifically Homer, after his jerkass tendencies reaches new heights.
  • Meaningful Name / Names to Run Away from Really Fast: Harm's name is a pun on the phrase "Constant Harm," implying that she likes issuing cruel punishments to people in her courtroom.
  • Transgender: In her first appearance, when Bart appeared in her courtroom to defend his parents, she said to him, "You remind me of me, when I was a little boy."

    Lionel Hutz 
https://static.tvtropes.org/pmwiki/pub/images/lionel_hutz_3.png
Debut: "Bart Gets Hit by a Car"
Final Episode: "Realty Bites"

A lawyer in Springfield, albeit an incompetent one. Voiced by: Phil Hartman


  • The Alcoholic: As implied in "Marge in Chains." He even argues his case before the court and is then informed he isn't wearing any pants. He's also seen drinking scotch at nine-thirty in the morning, which he justifies by claiming that he hasn't slept in days. In front of clients, no less.
  • Ambulance Chaser: In "Bart Gets Hit By a Car", Homer says upon meeting him, "You were the guy chasing Bart's ambulance."
  • Cloud Cuckoolander: He has shades of it, including contradicting himself midsentence and at one point forgetting what a lawyer is.
  • Chuck Cunningham Syndrome: All of Hartman's characters were retired after his death, as production thought it would be in poor taste to simply replace him. (The fact that his children would be watching was often cited.) There is the very rare occasion where they will turn up in the background, though, and they continue to have speaking roles in the comics.
  • Epic Fail: He managed to screw up a case where he stole the verdict and rewrote it.
    Judge: This verdict is written on a cocktail napkin. And it still says 'guilty!' And 'guilty' is spelled wrong!
  • Foil: To the Blue-Haired Lawyer.
  • Frivolous Lawsuit: His usual thing. Heck, he once sued the makers of The Never Ending Story for false advertising.
  • Make the Dog Testify: Does this occasionally.
  • Omnidisciplinary Lawyer: Lionel Hutz usually practices civil law, but he has taken cases as a prosecutor and a defense attorney as well (one time as a court-appointed attorney, in fact) and even represented them in a child custody case once. His record in any branch of law isn't all-too good.
  • The Pollyanna: Despite his constant failures, he always maintains his cheerful radio-announcer voice.
  • Smart Ball: Believe it or not, he occasionally catches this:
    • When Homer sued the Frying Dutchman restaurant for throwing him out before he had all he could eat, Hutz won the case by making Marge testify and forcing her to admit the absurd lengths she and Homer went to try and find another all-you-can-eat fish restaurant after they got kicked out (notably, they went fishing) and won the sympathy of a jury full of fat people.
    • When Homer tried to sue Moe for stealing the recipe for the Flaming Moe, Hutz researched the case law proving that beverage recipes couldn't be patented. Hutz was notably surprised at the fact that the books in his office didn't just make the room look good, but that they were also filled with all sorts of interesting legal tidbits.
    • When Bart sued the Krusty Corporation when he got hospitalized from eating Krusty-O cereal, Hutz won Bart a $100,000 settlement...of which Bart got only $500, since he used most of it to hire other, presumably more competent lawyers to help him.
  • Ultimate Job Security: Frequently lost his cases, but kept getting hired by Homer and Marge regardless. Lampshaded:
    Marge: You know, we should really stop hiring him.
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    The Blue-Haired Lawyer 
https://static.tvtropes.org/pmwiki/pub/images/blue_haired_lawyer2.png

Debut: "Bart Gets Hit by a Car"

Springfield's most prominent lawyer, known for his pasty face, blue hair, New York accent and nasal voice. Voiced by Dan Castellaneta.


  • Amoral Attorney: Although unlike most examples, he isn't outright malevolent.
  • Artistic License – Law: A Running Gag is that he'll claim copyright infringement over things that are in the public domain, like Christmas carols. One Halloween episode has him making a solid legal document that would allow Burns to hunt people.
  • Bullying a Dragon: He found out the hard way that trying to intimidate ex-Green Beret Seymour Skinner wasn’t the best idea.
  • Bunny-Ears Lawyer: Amoral, greedy and nasally sounding but he is the only competent lawyer in town and does win his cases often.
  • Disney Owns This Trope: He often threatens to sue people just for making references to copyrighted material.
  • Foil: To Lionel Hutz. More competent but even more amoral.
  • Four Eyes, Zero Soul: Has distinctly green-rimmed glasses and every single one of his appearances involves him being an Amoral Attorney supreme.
  • Gunboat Diplomacy: In several of his appearances he enforces his order for people to cease and desist by bringing along two gigantic goons for intimidation that then proceed to destroy whatever was allegedly breaking copyright.
  • No Celebrities Were Harmed: Word of God says he's based on the appearance of actor Charles Lane and the voice and mannerisms of real-life sleazebag lawyer Roy Cohn.
  • No Name Given: His actual name has never been revealed.
  • Omnidisciplinary Lawyer: He seems willing to take both civil and criminal cases. He also occasionally appears to serve as a prosecutor.
  • Satellite Character: He most commonly appears as the lawyer arguing against the Simpsons whenever they wind up in court. However, he has attempted to aid the Simpson family at least once.
  • Too Dumb to Live: In the Halloween episode above, he is shot right after giving the document that makes it legal for Burns to kill him. From what we see, he just decided to help Burns get a bulletproof legal defense for his hunting — because he's Burns' lawyer — without even trying to bargain to be spared in return.
  • You Gotta Have Blue Hair: Has blue hair.

Police

    Chief Clancy Wiggum 
https://static.tvtropes.org/pmwiki/pub/images/chief_wiggum.png

"I'd rather let a thousand guilty men go free than chase after them."

Debut: "Homer's Odyssey"

Chief of Springfield Police Department, Chief Wiggum is portrayed as lazy, gluttonous, out of shape, incompetent (if not mildly corrupt) and dim-witted. Voiced by Hank Azaria.


  • Artistic License – Gun Safety: Parodied. He's known to misuse his gun in ways that would surely get him killed. Whenever it does go off, it just barely misses him, which doesn't deter Wiggum in the slightest.
  • Bad Cop/Incompetent Cop: Although he and his men tend to lean more towards ignorant and bumbling. They can be corrupt but aren't usually too viciously (although they are corrupt, no doubt about that). The motto engraved into their badges is "Cash Bribes Only."
    Smithers: Shouldn't we call the police?
    Mr. Burns: Every last one is on the take! And I should know, I'm the one on the give.
  • Bait-and-Switch: When Marge says she wants to become a cop, Wiggum and the rest of the station begin laugh hysterically for several moments... before he gladly welcomes her aboard. When she resigns, they again start laughing, before saying that she'll be missed.
  • Book Dumb: He is completely ignorant of Springfield's laws, makes up his own laws on the fly and often quotes sayings from the police handbook which cannot actually be found in the book ("like the book says, if you can't beat them, join them").
  • Brilliant, but Lazy: The episode "Pranksta Rap" reveals that if he's motivated enough, he can make some great police work.
  • Catch-Phrase: Played with in "Behind the Laughter", in which he claims to have one.
    Wiggum: N'yeah! Wah! Wah-wah-wah! No, I lost it.
  • Characterization Marches On: In early episodes he is portrayed as a serious, no-nonsense police officer surrounded by idiotic, corrupt officers (though still with the smarmy voice and could join in on occasion). Later on, he becomes an idiotic and corrupt police officer, whilst the others become somewhat smarter. Not coincidentally at all, this was around the same time the writers decided to make him Ralph's father.
  • Depending on the Writer: Depending on what the situation requires, he can be motivated but incompetent, competent but villainous, lazy/apathetic, or brutally harsh.
  • Dirty Cop: He accepts (and often expects) bribes.
  • Doting Parent: His saving grace is his interactions with Ralph: Clancy is very encouraging of his son, and they have a very close and healthy relationship. Arguably, they're the most well-adjusted parental relationship on the show.
  • Fat Bastard: Apathetic, self-interested, and more than willing to abuse his authority for his own gain. He does love his son though.
  • Fat Idiot: He is one of the fattest characters (his pants are size 56 and his underwear has to be made in a Norwegian town) and one of the dumbest.
  • Fat Slob: Big eater and out of shape.
  • Genre Savvy: Is the Trope Namer for the Retirony trope, telling his financial advisor in the Season 12 episode "Homer Vs. Dignity" that he's not going to save his money for the future because, like all cops on TV shows and movies, he'll be killed in the line of duty just days before he retires... which is actually a Running Gag regarding the Springfield Police Department's equipment.
  • Hidden Depths: Actually managed to outwit the FBI and Mr. Burns. And while he is a completely inept and corrupt cop, he does it to provide for his family.
  • Inspector Lestrade: When Bart and/or Lisa play Amateur Sleuth.
  • I Owe You My Life: In "Mother Simpson," flashbacks reveal Wiggum had asthma, but Mona and her group's releasing Burns' germs cured him—allowing him to join the police academy. Years later, he repaid the favor by tipping Homer off about the authorities coming for Mona.
  • Juggling Loaded Guns: Has a frequent tendancy to do this.
    (on Homer) "Well, if it isn't that stupid cop from TV." (proceeds to scratch his ear with the barrel of his gun) "Oh yeah, that got it."
  • Military Moonshiner: Season 5's "Marge On The Lam" depicts Wiggum stumbling upon Homer after emerging from his private alcohol refinery.
    "Ahh! there's nothing like moonshine from your own still!"
  • The Nicknamer: It seems like the only part of his job he's passionate about is coming up with clever names for the people he arrests.
  • Nobody's That Dumb: He tends to have these types of moments.
    • In Season 14, "The Dad Who Knew Too Little", when Lisa is framed for a crime she didn't commit and the cops see her and Homer flee when they arrive to arrest her, Chief Wiggum said something that even his own son, Ralph, knew the answer to:
    Chief Wiggum: (to Marge) Would an innocent person flee?
    (beat)
    Chief Wiggum: No, really. Tell me. I honestly don't know.
    Lou: Chief, no.
    Ralph: Even I knew that.
    Chief Wiggum: Yeah, yeah, I'm not... I'm not good.
    • In Season 23's "At Long Last Leave", after the Simpsons are banished from Springfield, Homer and Marge sneak back into Springfield under the disguise of Mr. Burns and Smithers. When Chief Wiggum first spots them, it appears that he falls for it but it's later revealed that he had seen through their disguises and only pretended to be fooled in order to have time to rally the people to arrest Homer and Marge.
    Chief Wiggum: You really thought you could fool me with that Burns and Smithers getup. I mean, I'm not the sharpest pencil in the pencil thing, but I'm least as smart as a cat. Right, Lou?
    Lou: Uh, what breed, Chief? I mean, I saw an Abyssinian once who could change channels.
    Chief Wiggum: Eh, that is pretty smart.
  • Oddly Small Organization: Although other members are sometimes seen, a couple episode have jokes the the Springfield Police Department only has three members.
  • Police are Useless: The poster trope. Just see all the examples posted in the Western Animation trope page. He has a few competent moments, but these are far and between.
  • Reckless Gun Usage: He's been known to use his gun to crack nuts or change channels on the tv, instead keeping the remote in his holster.
  • Suspect Is Hatless: He provides the Trope Namer in "Homer's Triple Bypass".
  • Stripper/Cop Confusion: Went along with it for the money.
  • Sympathetic Inspector Antagonist: Sometimes, when played sympathetically.
  • Visual Pun: He's a police officer who looks like a pig.
  • Vitriolic Best Buds: He has a strained relationship with Mayor Quimby. Earlier on, both men vied to have control over the city, with Wiggum seeing Quimby as unfit to be mayor (which more than once led to serious arguments, particularly during the Monorail crisis). As Wiggum's competence evaporated, he became the Mayor's lapdog, although he often resents Quimby's lack of gratitude.
  • You Gotta Have Blue Hair: During the show's first two-and-a-half seasons, he had black hair, turning blue halfway through the third season.
  • Your Cheating Heart: There have been occasional glimpses that show that Chief Wiggum isn't entirely faithful to his wife Sarah. Such as in "Cape Feare".

    Sergeant Lou and Officer Eddie 
https://static.tvtropes.org/pmwiki/pub/images/lou_and_eddie.png
Debut: "There's No Disgrace Like Home"

Chief Wiggum's seconds-in-command. Voiced by Hank Azaria and Harry Shearer.


  • Ambiguously Human: When they see Comic Book Guy and Agnes Skinner in bed together and Eddie looks like he's about to be sick. Lou reassures him that it doesn't affect him because he's not human.
  • Butt-Monkey: Whenever Lou raises minor objections, he will usually get chewed out for complaining by Chief Wiggum. Eddie is the one who gets injured.
  • Catch-Phrase: Lou says, "Uh, Chief?"
  • Cloudcuckoolander's Minder: Became this to Wiggum in later seasons.
  • Dirty Cop: Early in the series, they were shown harassing civilians and locking them up because they didn't like them. This aspect was later excised as they became Wiggum's retainers.
  • Flat Character: Eddie. The episode "Pranksta Rap" reveals that not only is he below Lou's rank but his place can be vacant because they don't need an Eddie.
  • No Celebrities Were Harmed: Hank Azaria based Lou's voice on Sylvester Stallone.
  • Only One Name:
    Guy: Now what are your last names?
    Lou: We don't have them. We're like Cher.
  • Only Sane Man: Zigzagged. Lou sometimes appears more competent than Wiggum, but he is also capable of being corrupt.
  • The Quiet One: Eddie is usually quiet, though he used to be a bit more chopsier and talked more than he does now.
  • Race Lift: Lou was yellow in earlier episodes but is now black.
  • Salt and Pepper: Lou is the Pepper to Wiggum's and Eddie's Salt.
  • Stripper/Cop Confusion: See Wiggum's entry, he called them as reinforcement. Lou was quite eager to assist.
  • Those Two Guys: Though Eddie hardly ever speaks and it's Lou that gets the bulk of the characterization.

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Criminals

    Robert Underdunk Terwilliger, Jr., Ph.D. (Sideshow Bob) 
https://static.tvtropes.org/pmwiki/pub/images/50254_35914458394_6347051_n_390.jpg

Debut: "The Telltale Head"

A man cursed to have both huge feet (standard floppy clown shoes fit him perfectly) and a natural hairstyle like a palm tree while also having the mind of a keen intellectual, he was, while originally not interested in becoming a performer, coaxed into joining the Krusty the Clown Show with the prospect of appealing to a huge audience of children with his own brand of edutainment. To his horror, though, his ideas were all ignored and he became the abused straight-man for Krusty's lowbrow slapstick. Jealousy and resentment eventually led to him framing Krusty and then assuming control over the show while Krusty was imprisoned, but Bart Simpson exposed him and sent him to prison. As a result, he carries a murderous grudge against both his former "partner" and the Simpson boy. Voiced by Kelsey Grammer.


  • The Ace: Bob is impressively multitalented at almost everything he does except trying to kill Bart or dealing with Bart's interference. He's skilled at everything from music to acrobatics to biochemistry to construction management to politics, speaks multiple languages and is highly knowledgeable of literature and philosophy.
  • Affably Evil: From time to time, he's portrayed in a more genuinely likeable light. Of course, this doesn't stop him from being a ruthless criminal.
  • Anime Hair: He could be mistaken for a palm tree with the right dye.
  • Arch-Enemy: Bart Simpson and Krusty the Clown. And rakes.
  • Artifact Title: He continues to go by his stage moniker long after his career with Krusty ended in "Krusty Gets Busted". He doesn't seem to mind being called by this name either; he doesn't correct anyone or get mad when anyone refers to him as such. Even his mayoral campaign ads say "Vote for Sideshow Bob" as opposed to "Vote for Terwilliger" or simply "Vote for Bob". The only time he ever seems to get angry at the name is when he is about to crash a plane into Krusty in "Sideshow Bob's Last Gleaming". Bart begs him not to saying that Krusty "made [Bob] into who he is" and without him he wouldn't even be known as "Sideshow". Bart's plea just makes Bob scream in fury while he increases the speed of the plane.
  • Ascended Extra: Bob first appears as a silent background character in "The Telltale Head".
  • Ax-Crazy: He started to qualify for this when his attempts to kill Bart escalated.
    • He tries to have him cremated alive in "Funeral for a Fiend".
    • In "The Bob Next Door" He visibly removes his cell mate's face and cuts off his own.
    • He also ties up Bart while singing casually about wanting to gouge out his eyes.
    • And then there's the "Treehouse of Horror XXVI" segment "Wanted: Dead, Then Alive", which has several moments that are genuinely disturbing.
  • Big Bad: Of The Simpsons Ride.
  • Big-Bad Ensemble: With Mr. Burns. Sure, Burns might be the most influential villain in Homer's life, but Bob is the most dangerous and active threat to the Simpsons.
  • Bi the Way: He off-handedly mentions experimenting during college when Homer is surprised that he has a wife...
  • But Not Too Bi: ...although he's never shown to be attracted to any men during the course of the series.
  • Butt-Monkey: Many of his appearances involve some physical or mental suffering. "Cape Feare" may be the best example, given what he goes through under the car or when a parade (complete with several elephants) tramples him. Despite his infamy, he has never actually succeeded in killing anyone (except for Hans Moleman in "The Man Who Grew Too Much", but it was an accident that he isn't even aware of). The poor guy can't even win against a rake.
  • Camp Straight: A Shakespeare-quoting, musical theatre-loving, highly cultured psychopath who, despite his effete tendencies, is attracted to women. It's also downplayed in that he's actually bisexual (see Bi the Way above); Homer lampshades this trope when, in "The Italian Bob," he assumed that Terwilliger was "out loud and proud" because of his stereotypically homosexual interests.
  • Card-Carrying Villain: He's an Evil Genius and he's not particularly modest about the fact, either.
  • Catch-Phrase: "Hello, Bart".
  • Characterization Marches On: He was originally Krusty's non-speaking sidekick in early episodes.
  • Classically Trained Extra: Much to his dismay.
  • Complexity Addiction: He can't simply gut Bart with a knife.
  • Death Trap: Subverted when it appears that he is planning to kill the Simpsons family by using an explosive computer. It later turns out that his real plan was to trick Springfield into hating Bart and then burn him alive in a coffin when he went to the seemingly deceased Sideshow Bob to make amends.
  • Dick Dastardly Stops to Cheat: In "Sideshow Bob Roberts", Bob steals an election in which Quimby was already a sure loser.
  • Dub Name Change:
    • In the French dub he is known as "Tahiti Bob" (due to his hairdo maybe?). Probably because "sideshow" doesn't translate well in French.
    • In German he is "Tingeltangel-Bob" (roughly: Vaudeville Bob). "Sideshow" doesn't translate well into German either.
    • In Russian he is "Второстепенный Боб" (secondary or accessory Bob). "Assistant Bob" and "Bob the Comedian" are also used.
    • In the Latin American dub, he is "Bob Patiño", patiño being a term to denote a person whose intended purpose is to be the subject of mockery, mistreatment and humiliation in order to entertain others.
  • Easily Forgiven: Depending on the Writer, sometimes the family will hate him for his murder attempts whereas other times they'll let bygones be bygones. An example would be when the family was OK with him marrying Selma, other cases were keeping his criminal past a secret so he can fix their car and Lisa being his lab partner with gene splicing vegetables. Bart is the only one who holds a justifiable grudge against him.
  • Enemy Mine: Bob has had to help the Simpsons stop a common enemy at least two times. Downplayed in "Wedding for Disaster", where he merely offers Bart and Lisa a clue to what they're looking for.
  • Enmity with an Object: Rakes, ever since the Overly Long Gag in "Cape Feare" where he stepped onto dozens of them, causing each one's handle to spring up and hit him in the face. His hatred of them possibly extends to before this. He has even called them his old arch-enemy, above Bart.
  • Even Evil Has Loved Ones: Although the rest of the townspeople in Italy turn against him after Lisa reveals his criminal past, his wife and son still love him and join him in his vendetta against the Simpsons.
  • Even Evil Has Standards: He once tried to kill Krusty by brainwashing Bart into suicide bombing him, but then tried to stop that from happening when he found out that Krusty misses him.
  • Evil Brit: By voice and mannerism, but most episodes implies it's Foreign Culture Fetish (his mom is a big Shakespearean actress, he states that he is American multiple times, took a bunch of pictures of Buckingham's castle when he went visiting, etc.).
  • Evil Genius: A manipulative, Yale-educated psychopath.
  • Eviler Than Thou: His brother Cecil, until "Funeral For a Fiend", when he tries to burn Bart alive after successfully convincing everyone to hate him. Bob however never saw Cecil as eviler or better.
    Cecil: And it was my portrayal as the grieving brother that sealed the deal!
    Bob:Yes, and Hamlet is all about Laertes!
    Cecil: Would you please stop comparing me to Laertes!
  • Evil Redhead: A villain whose defining feature is his curly, palm tree-shaped red hair.
  • Evil Sounds Deep: Kelsey Grammer gives him a chilling deep voice, which makes it all the more appropriate for Bob.
  • Failure Is the Only Option: His plans to kill Bart.
  • Fatal Flaw: His massive ego. It's not enough that he's brilliant—everyone has to know he's brilliant. This pride occasionally destroys his plots:
    • In "Cape Feare," Bob has Bart cornered on a houseboat, with no one else around, and could take him down with a single blow. He offers the boy a "last request," and Bart, knowing Bob prides himself on his singing voice, requests to hear the entirety of Gilbert and Sullivan's H.M.S. Pinafore. The killer gleefully agrees and sings every part of the two-hour-plus work, leaving him at the mercy of the police when he shows up. For such a smart guy, you'd think he would recognize the trick.
    • In "Sideshow Bob Roberts," Bart and Lisa discover that he stuffed the ballot box in his mayoral campaign with dead voters' names. Rather than accuse him outright, they suggest that he was a patsy to another prominent Springfield Republican who actually cooked up the scheme. Bob can't stand the notion and quickly produces massive amounts of evidence proving that the plan was all his idea...after which he's promptly arrested for his crimes.
    • Bob eventually uses this against Bart and Lisa in "Funeral for a Fiend." His initial plan to kill the Simpsons involves tying them up in a phony restaurant and leaving a laptop with a faulty battery to catch fire and incinerate the family. As he's leaving, he quotes a passage from Macbeth, but gives the wrong scene number. Lisa smugly corrects him—and he promptly marches to the laptop to prove that he's right, which ends up foiling the plan...or rather, sets up the real plan to fake his own death.
  • Faux Affably Evil: He's usually rather polite, soft-spoken and funny... though he's a psychopath and tries to kill a 10 years-old boy nonetheless.
  • Flanderization: In his first six episodes he only tried to kill Bart once. He originally framed Krusty to make the show more educational, he wanted Selma's money, he wanted to wipe out television, he rigged an election, and tried to do a Heel–Face Turn (though some of these included personal threats to Bart, like holding a knife to his throat as a hostage, and his "Bart killing policy" during his mayoral campaign). Ever since "Day of the Jackanapes" almost all of his appearances have him trying to kill Bart. "The Man Who Grew Too Much" is an exception, as in that episode he wanted to genetically manipulate himself to become an unstoppable supervillain and only went after Bart and Lisa when they started messing with him.
  • Friendly Enemy: 24 long years of familiarity has dulled the terror and rage between Bart and Bob, so much so that Bart casually greets him like meeting an old friend at one point, and Bob asking the children to remove the "Sideshow" from their scream of terror since they have known each other for so long.
  • Frame-Up: He attempts to frame Krusty by dressing in a Krusty costume and arm rob the Kwik-E-Mart in Krusty Gets Busted.
  • Had to Come to Prison to Be a Crook: The first time he crossed paths with the Simpsons, he mostly just wanted to frame Krusty for robbery, as opposed to trying to kill anyone, and had a good reason to do so. Then he wanted to kill Selma for her money, and he only gets worse from there.
  • Hates the Job, Loves the Limelight: This trope is what led to Bob's Start of Darkness. He accepted Krusty's job offer because he originally wanted to do a show that would be both entertaining and enlightening to the children who watched it, but his talents were utterly wasted on Krusty's lowbrow slapstick. Finally having enough, he framed Krusty for armed robbery so he could take over the show and remold it into what he wanted to do. Bob had finally realized his dream, and his show was earning great ratings... and then Bart exposed him for framing Krusty. And while he hated the indignity of being the put-upon sidekick, when Krusty accidentally erased all those old episodes, Sideshow Bob vowed revenge for him erasing his past.
  • Heel–Face Revolving Door: In "Brother from Another Series".
    Bob: You... you saved my life.
    Bart: Yeah, I guess that means you can't ever try to kill me again!
    Bob: [sinister] Oh, I don't know about that... Joking, joking!
  • Hereditary Hairstyle: He inherited his hair from his mother, which he then passed on to his son.
  • Hypocrisy Nod: He announces his intention to eradicate television from Springfield via JumboTron at an air show in "Sideshow Bob's Last Gleaming", then comes back to amend himself: "By the way, I'm aware of the irony of appearing on TV in order to decry it, so don't bother pointing that out."
  • Insane Troll Logic: One of the Bob for Mayor ads in "Sideshow Bob Roberts" accuses Quimby of being soft on crime... for ordering Bob's release.
  • Insufferable Genius: Toward Cecil where he mocks for going to Princeton among other things.
  • Iron Butt Monkey: Rivals Homer in this regard. In "Cape Feare" alone he gets trampled by elephants, dragged through a cactus patch, accidentally steps on many, many, rakes, and has hot, scalding coffee poured on him.
  • Ivy League for Everyone: Bob went to Yale.
  • Kick the Dog: Really likes doing this, especially when he's not a Butt-Monkey.
  • Knight of Cerebus: Played with. He's a persistent attempted murderer in a family sitcom, if still a very comedic one.
  • LEGO Genetics: Gave himself superpowers by splicing his DNA with various animals. These abilities never show up again but the episode was implied to be All Just a Dream that Flanders was having.
  • Leitmotif: The theme from ''Cape Fear''.
  • Manipulative Bastard: Being a comedic center of a lot of villainous staples, Sideshow Bob has dabbled in the art of the manipulative bastardry on more than one occasion.
  • Monster Clown: Well, ex-clown.
  • Motive Decay: While he's almost always intended to kill Bart out of revenge for foiling his schemes, he goes so far as to side with his brother against him, even though his brother tried to kill him, embezzle a lot of money, destroy the town, and frame Bob for the latter two. He does give up on killing Bart but then shenanigans by the Simpsons made him declare a vendetta toward them as a whole and he still primarily aim to assassinate Bart.
  • Mundane Utility: Bob's overly large feet were what allowed Bart to bust him for framing Krusty in the first place. However, when he moved to Italy he found that his feet made him a natural at crushing grapes for wine. This endeared him to the locals, and eventually made him Mayor of his community.
  • Odd Friendship: With Snake. The two are often cellmates and will usually hug each other when one or both are released.
  • Overarching Villain: Starting with the very fact that he is Bart's most personal enemy whose attempts to kill him go back more than 20 years... our time, anyway. He is also the most active threat to the Simpson family.
  • Pet the Dog: He has some. When Krusty's father dies, he comes to comfort him. He also saves Bart from his brother once, and refuses to team up with Lassen when this latter proposes to kill Bart together.
  • Phrase-Catcher: "AAAGH! Sideshow Bob!" Played with in "The Great Louse Detective" thusly:
    "Oh, please, children. We've known each other so long, just call me Bob."
    "AAAGH! Bob!"
  • Reformed, but Rejected: Sideshow Bob really tried to live a honest life in "Brother from Another Series", but Chief Wiggum stubbornly refused to believe him to be innocent regarding Cecil's plot in that episode. He also became Happily Married and rose to the position of Mayor of a small town in Italy, while accomplishing honestly good deeds. However, when Lisa accidentally spilt the beans on his former life, the entire town threw him out and left Bob and his new family now ready to vow revenge against the Simpsons for ruining their life.
    Gino: Vendetta! Vendetta!
  • Sadist: He always tries to kill Bart with a sadistic joy.
  • Sanity Slippage: More and more as the series progresses. Bob has always been a psychopath, but he is becoming more Ax-Crazy, sadistic, and obsessed with Bart.
  • Selective Enforcement: He originally only desired revenge against Bart, no matter how much others crossed him, holding nothing against the rest of the Simpson family despite a increasingly similar amount of suffering they had caused. This was especially noticeable for Lisa, who ruined his plans more times than Bart. This was dropped as he declared vendetta on the whole family after the incident in Italy, but he still wants Bart more than the others.
  • Shout-Out: He and his father, Dr. Robert Terwilliger, Sr., are mistakenly believed to be named after Dr. Terwiliker from The 5000 Fingers of Dr. T; their actual namesake is Terwiliger Boulevard in Portland, Oregon, the hometown of Matt Groening. It's an honest mistake though, considering Dr. Terwiliker finds himself at odds with a boy named Bart.
  • Sins of Our Fathers: Bob is willing to kill Maggie in "The Italian Bob" just because she's a Simpson.
  • The Sociopath: He meets all the criteria of a sociopath. He is ruthless, manipulative, intelligent, sadistic, brutal and deeply obsessed with killing a 10-year-old boy.
  • Soft-Spoken Sadist: Thanks to Kelsey Grammer's delivery.
  • Status Quo Is God: He will always have a venomous hatred of Bart and Krusty, despite having made up with each of them at least once. He's even sided with his brother Cecil against Bart, even though Cecil tried to frame and murder him and Bart saved his life from Cecil. He'll always end up back in jail by the end of each episode, no matter what deception he used to get himself out. Wiggum at one point sent him back in with no evidence, seemingly just to enforce this trope.
  • Unholy Matrimony: With Francesca, his Italian wife. At first she knew nothing of her husband's multiple murder attempts. When she does become aware, she helps Bob try to kill the Simpsons family.
  • Vile Villain, Saccharine Show: Like Mr. Burns, Sideshow Bob is usually portrayed more seriously than other villains on the show, though he does have some comic relief moments.
  • Villain Decay: Played with. Bob is always devious and brilliant and a serious threat in every appearance in which he's out to cause the Simpsons pain, but Bart has foiled his plans so often that neither he nor the rest of his family are as afraid of him as they were in his first few appearances.
    Bart: Oh, it's you, Bob. How ya doin'?
    Bob: No scream? Not even an 'eep'?
    Bart: Hey, I'm not afraid of you. Every time we tango you end up in jail. I'm 6-0.
  • Villainous Friendship: Has one with Lisa in "The Man Who Grew Too Much".
  • Villainous Rescue: Has saved the lives of Bart and Lisa in "Brother From Another Series", Krusty in "Day of the Jackanapes", and Homer in "The Great Louse Detective".
  • The Voiceless: In his role as Krusty's sidekick, he never spoke and only communicated via slide whistle.
  • Vote Early, Vote Often: How he won the mayoral election in "Sideshow Bob Roberts", of the "Ghost Voter" variety. Of course, it might also qualify under Dick Dastardly Stops to Cheat.
  • Wanting Is Better Than Having: He decides not to kill Bart when he gets the chance as chasing him gives him something to live for.
  • Well-Intentioned Extremist: In "Krusty Gets Busted", his first appearance, Bob gets Krusty framed for armed robbery so he can take over the show and turn it into educational programming.
  • Wicked Cultured: Oh, yes. He hates having been a clown, believing it destroyed "more minds than syphilis and pinball combined", and despises television, deriding the medium as a "bottomless chum-bucket".
  • Would Hurt a Child: Finally gets the chance to kill Bart (a lot) in the non-canon "Treehouse of Horror XXVI" segment "Wanted: Dead, then Alive", after "24 years of trying to kill a ten-year-old child".
  • Worthy Opponent: Oh, Bob is not shy about expressing how much he hates Bart and his wish to destroy his life, but all the same he has an undeniable admiration for the boy's tenacity, cunning and bravery. To a lesser extent, Lisa also earned Bob's respect after thwarting multiple schemes of his with her ingenuity and sharp wit.
  • You Meddling Kids: In "Krusty Gets Busted" (Sideshow Bob's first speaking appearance) he takes this to its logical conclusion, adding "Treat kids as equals! They're smarter than you think!" Considering that he had spent most of his time that episode running quality children's programming, it's an especially good point.
  • You Will Be Spared: Has outright stated that he is only interested in killing Bart. He has lampshaded his apathy towards Lisa on several occasions, even when she is the one who stops him. Bart will always be his Arch-Enemy. While he declares vendetta on the whole family (yes, including Maggie) after they ruin his life in Italy, future episodes show that he still wants Bart dead first and just sees the rest of the family as acceptable targets.

    Chester Turley (Snake Jailbird) 
https://static.tvtropes.org/pmwiki/pub/images/snake_jailbird_1.png

Debut: "The War of the Simpsons"

A recurring petty thug and minor crook, most often seen mugging people or holding up the Kwik-E-Mart. Voiced by Hank Azaria.


  • Adventurer Archaeologist: He was formerly an idealistic Indiana Jones-type archaeologist, but became a thief.
  • Affably Evil: In more recent seasons. He brings his kid to his robbery.
  • Animal Motifs: He's obviously themed around snakes. As shown by his name, tattoo and car decoration of a cobra.
  • Animal Theme Naming: He's a criminal themed around snakes.
  • Anti-Villain: Again, in more recent seasons. "Goodbye, student loan payments!"
  • Berserk Button: Snake hates singing.
  • Card-Carrying Villain: In earlier seasons. For example, this quote from Season 4:
    Snake: (on breaking out of jail) All right! Time for a crime spree!
  • Catch-Phrase:
    • "Bye!" and "All RIGHT!"
    • "Dude!"
  • Cool Car: Is often seen driving 60s muscle cars. The B-Plot of "Realty Bites" involves him trying to get his prized 68 Firebird "Little Bandit" back from Homer who bought it at a police auction.
  • Despair Event Horizon: In "The Seemingly Never-Ending Story", it's revealed that his crimes against shopkeepers stem from an incident in which a certain barkeeper note  took Maya coins from him as he was handing them over to the museum.
  • Disproportionate Retribution: Once broke out of prison and attempted to murder Homer, simply because he'd bought Snake's prized getaway car "Lil' Bandit" at a police charity auction... and gave her the wrong fuel.
    Snake: That smells like regular! She needs Premium, Dude... Premium!... Dude!
    • He also turned to crime because Moe stole his bag of Mayan coins that he was planning on donating to the museum. Springfield didn't have to suffer for Moe's crime and he could have tried solving it himself since the police in Springfield are useless and incompetent with crimes that haven't affected them personally.
  • Even Evil Has Loved Ones: Has a Generation Xerox son, and a long-term girlfriend.
  • Even Evil Has Standards: He once abandoned a telemarketing scam because he doesn't like bothering people at home.
  • Go-Karting with Bowser: He is often seen doing things with the police like joining their bowling team and appearing in their calendar.
  • Good Parents: Although Snake seems to have committed every crime possible, he is an extremely good father to his son.
  • Karma Houdini: Snake is constantly seen getting arrested, but never appears to stay in prison for a long time.
  • Like an Old Married Couple: With Apu. They once attended couples counselling.
  • Older Than They Look: Based on flashbacks, he's probably already close to 40, but he still appears to be around his mid to late 20s.
  • Perma-Stubble: Even on the few occasions he's tried to clean up the five-o'-clock shadow remains.
  • Pet the Dog: He is at one point implied to have a soft spot for puppies and other animals, as he, after being given one of Santa's Little Helper's Poodle/Greyhound puppies, promises to take care of it (albeit in a similar manner to trying to kidnap someone), as well as rubbing it affectionately.
  • Surfer Dude: He speaks with a "Valley Boy" accent.
  • Steal the Surroundings: He robs the Kwik-E-Mart. Literally. He loads it onto a flatbed truck and drives it away.
    Snake: All right! I'm taking this thing to Mexico!
  • Tattooed Crook: His nickname comes from the prominent tattoo of a snake on his arm.
  • Totally Radical: Not only his language but his tone of voice is positively gnarly.
  • Unholy Matrimony: Is often seen with his girlfriend, Gloria, who left him for Mr. Burns, but then came back when she saw that Mr. Burns was truly evil, not just a bad boy like Snake.
  • Villains Out Shopping: Sometimes he just hang out with his son or even Apu.
  • Villainous Friendship: He and Bart Simpson. He encourages Bart to play with his son, help him hide in his treehouse in exchange for gifts and after the end of a strike, convinces Bart to help him escape.
  • What the Hell Is That Accent?: It sounds like a bizarre cross between upper-class British English, Cockney, Australian and Californian.
  • Would Hit a Girl: He tried to attack Marge with a knife but she defeats him by hitting him with a bin lid.

    Marion Anthony "Fat Tony" D'Amico 
https://static.tvtropes.org/pmwiki/pub/images/190px-FatTony_2308.png

Debut: "Bart the Murderer"

Head of the Springfield Mafia. Voiced by Joe Mantegna.


  • Affably Evil: Depending on the episode really.
  • Ambiguously Bi: Mob boss Fat Tony had a wife (now deceased), but also expressed interest in Homer during the latter's time as The Mole for the police. He described it as "heterosexual male friendship like the Greeks wrote about", which is an extremely ambiguous line.
  • Ascended Extra: Another one of those characters that Word of God expected to appear only once, but kept coming back.
  • Badass in Charge: He, Legs, and Louie once took on a Yakuza group, and held their own, despite being underarmed and undermanned.
  • Characterization Marches On: He had a thick Bronx accent in his first appearance.
  • Even Evil Has Loved Ones:
    • In "The Mook, The Chef, The Wife and her Homer" he explains his wife was "whacked by natural causes", in "Donnie Fatso" he takes an undercover Homer to her grave and cries in front of him. Being unable to see Marge at the time, Homer starts to sympathize with him.
    • His son/nephew Michael, even though their relationship has problems, he clearly loves his son and after his death his cousin seems to have taken him in.
    • Fat Tony and Fit Tony were this to each other, as demonstrated by the picture the latter shows Homer upon introduction.
  • Exact Words: Fat Tony loves invoking these tropes.
    • One instance was when, after Homer lost some money he borrowed from him in a football bet, Fat Tony, who learned of this, stated that Homer shouldn't worry, as he's sure that they'll "hammer out a payment plan". When he said "hammer out" a payment plan, he meant this literally, and certainly wasn't kidding, as he meant that he was going to have his goons restrain Homer and whack his right hand with a hammer multiple times.
    • When he told his goons that Troy McClure "sleeps with the fishes", he wasn't using mafioso-speak.
    • There was his hilarious threat to the Mayor given directly to the camera on live TV: "Hello Mayor Quimby. I would just like to remind you that accidents will happen. Like the killing of you. By us."
  • Formerly Fit: How Fit Tony became an Identical Cousin.
  • Insane Troll Logic: He manages to justify stealing a truckload of cigarettes to Bart by likening it to someone stealing bread to feed a starving family.
  • Killed Off for Real: But replaced by his cousin.
  • Legitimate Businessmen's Social Club: Trope Namer.
  • The Mafia: He is the don of Springfield's mafia.
  • Meaningful Name: "D'Amico" roughly means "of friends" in Italian. Mafioso often refer to each other as "friends of ours" or "a friend of a friend".
  • My Sibling Will Live Through Me: Because Status Quo Is God, when he is killed off his cousin replaces him, soon becoming an exact copy of him.
  • Odd Friendship: Homer and Marge actually get along with Fat Tony quite well, despite knowing he's head of the Springfield Mafia and even having had their lives threatened by him on a few occasions.
  • Replacement Goldfish: He died and was replaced by his cousin Fit Tony, who then got fat and became the new Fat Tony.
  • Retcon: His real name. It has at various instances been given as William Williams, Anthony D'Amico, and Marion.
  • Stout Strength:
    • He is able to fight back yakuza despite his size and age.
    • Fit Tony also becomes this after overeating due to the stress of dodging assassination attempts.
  • Wicked Cultured: He was shown to be a quite talented violinist.

    Legs and Louie 
Debut: "Bart the Murderer"

Fat Tony's associates. Voiced by Hank Azaria (by Karl Wiedergott in "Trilogy of Error" and "Chief of Hearts") and Dan Castellaneta.


  • Back-Alley Doctor: Legs is apparently a mob doctor, and sews Homer's thumb back on in one episode. Lisa states that he's in for a long and agonizing recovery.
  • Hidden Depths: Louie can be seen attending the same rock'n'roll camp as Homer.
  • Mooks: Of Fat Tony.
  • Those Two Bad Guys: Never seen apart usually.

    Johnny Tightlips 
Debut: "Bart the Murderer"

A mobster and an associate of Fat Tony. Voiced by Hank Azaria.


  • Ascended Extra: He first appeared in a bit scene in "Bart the Murderer", went largely unused for the next 8 seasons, and was then reused for the gag below in "Insane Clown Poppy." Since then, he has become a semi-regular recurring character.
  • Even Bad Men Love Their Mamas: He goes through his usual routine about whether or not his car's outside until 1. he learns it's being towed and 2. "Hey, my grandma's in there!"
  • Foil: To Frankie the Squealer.
  • Lawful Stupid: A rare criminal example. Takes omertà so seriously that he won't give details to his own associates during critical situations, as demonstrated below.
  • Meaningful Name: 'Tightlips', apt name for a guy who says very little.
  • The Stoic: He keeps up his emotionless, tight-lipped persona at all times.
    • After getting shot, he refuses to disclose where he was hit.
    Louie: Johnny Tightlips, where'd they hit ya?
    Johnny: I ain't telling you nothin'.
    Louie: But what'll I tell the doctor?
    Johnny: Tell 'im to suck a lemon.
    • His friends do call him out on this.
    Fat Tony: (while being shot at) Johnny Tightlips! Can you see the shooter?
    Fat Tony: You know, you could be more a little helpful!

    Frankie the Squealer 
Debut: "Insane Clown Poppy"

A low-level member of the Springfield mafia and associate of Fat Tony. He is known, as his name suggests, for his indiscretion. Voiced by Dan Castellaneta.


  • Exactly What It Says on the Tin: He's a mobster who 'squeals' on his own mafia.
  • Foil: To Johnny Tightlips naturally.
  • The Friend No One Likes: The rest of the mafia clearly don't like him but he never goes anywhere.
  • Iron Butt Monkey: One Halloween episode had the mafia shoot him to no effect while he calls his wife and tells her he'll be home late.
  • Meaningful Name: Apt name for the guy really.
  • The Millstone: For the Springfield Mafia, given his squealing tendencies. It's a wonder why they haven't yet taken him out (or how he was even initiated into the mob in the first place).
  • The Stool Pigeon: He compulsively squeals about everything, because it makes him feel big. He even squeals while he's getting beaten up for squealing.

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