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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: "Bart Gets An F"

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".
  • Character Catchphrase: "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), and has openly admitted to using city funds to murder his enemies, and has to be reminded that they are supposed to have three million dollars instead of two million, implying he already skimmed off a million from Burns' environmental damage fine money.
  • Even Evil Has Loved Ones: Tried to use his influence to keep his nephew Freddy out of prison.
  • Everyone Has Standards: Quimby might be one of the most corrupt mayors known to fiction, but there are lines he won’t cross.
    • 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 completely mortified at himself when he found out that he was actually sleeping with his own niece, to the point that he called himself "an abomination" for it.
    • 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.
    • In The Simpsons Movie, when presented with irrefutable evidence that Lake Springfield is extremely close to an ecological disaster, he actually does his job for once, banning any dumping of trash in the lake, constructing a wall to prevent more of it, and organizes a full cleanup effort.
  • 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, despite not having much desirability in looks is more than made up for his political power.
  • Mayor Pain: Of the Incompetent Mayor Pain type. 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 that she is indeed his niece, he is both completely shocked and disgusted with himself. Even a sleazy womanizer like him has his limits.
  • 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 (mostly Ted), 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 lets Marge go without any charges after she blocked a bridge with her car during a massive breakdown. Granted he did it to keep the votes of women, but it was still kind.
    • He was willing to sacrifice television if it meant stopping Sideshow Bob from detonating a nuke.
    • Building Lisa a Mount Rushmore face in Springfield when she reaches second place in the spelling Olympics (and being genuinely proud of her). This also counts for the rest of Springfield.
  • 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 super train 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.
  • Too Many Babies: His many, many affairs have led to him fathering multiple children out of wedlock. One episode featured him facing some 27 separate paternity suits.
  • Verbal Tic: He frequently 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 to who takes over during an emergency on the Monorail crisis.

    State Comptroller Atkins 
Debut: "Lisa Gets an "A""

The comptroller of whatever state Springfield is in. Voiced by: Hank Azaria, Harry Shearer (when impersonated by Otto)

Judges and Lawyers

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

One of the main judges in Springfield. He is usually actually very good at his job. Voiced by Harry Shearer.


  • 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.
  • Inconsistent Coloring: He appeared as white (that is, yellow) in his first appearance in the first season and later appeared as black in a season three episode. Unlike in the cases of Smithers and Lou, he flip-flopped back and forth between the two skin colors, appearing with yellow skin as late as season ten. Since then, he has always been black.
  • No Celebrities Were Harmed: His overall look and persona is loosely based on Robert Bork (a fairly infamous figure at the time, having recently been rejected as a Supreme Court Justice).
  • Reasonable Authority Figure: One of the few people with authority in Springfield who is (usually) characterized as competent, non-brutal, and non-corrupt.
  • Sudden Name Change: Prior to season 4, he was known as Judge Moulton. This happened because Josh Weinstein didn’t know he had a name beforehand.

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

Occasionally replacing the Reasonable Authority Figure Judge Snyder, Judge Harm is a cruel Hanging Judge through and through. Voiced by Jane Kaczmarek.


  • Ambiguous Gender Identity: She says to Bart during his trial "You remind me of me when I was a little boy", but aside from Snake commenting on it, nothing else is ever said on the matter.
  • 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 and marriage 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.
  • Meaningful Name: Harm's name is a pun on the phrase "Constant Harm," implying that she likes issuing cruel punishments to people in her courtroom.
  • No Celebrities Were Harmed: Any resemblance between her and Judge Judy is certainly intentional.
  • Pet the Dog: In the 300th episode she does grant Bart emancipation from his family, specifically Homer, after his jerkass tendencies reach new heights.

    Lionel Hutz 
https://static.tvtropes.org/pmwiki/pub/images/hutz.png

"As for your case, don't you worry. I've argued in front of every judge in the state. Often as a lawyer!"

Debut: "Bart Gets Hit by a Car"
Final Episode: "Realty Bites"

A severely incompetent but determined lawyer, who usually works for the Simpson family. Voiced by: Phil Hartman


  • 30 Minutes, or It's Free!: In a deleted scene, he apparently has a "cases won in thirty minutes, or your pizza's free!" policy.
    Hutz: (Upon being informed that the case was won in his absence) Well that's okay, the box was empty!
  • 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."
  • Amoral Attorney: Though he's too incompetent to be especially dangerous, he has absolutely no problem with dealing under the table or falsifying evidence if he thinks it'll help his case. (It usually doesn't.) He also believes that, without lawyers, the world would be a Perfect Pacifist People Utopia — a thought which makes him shiver. When Bart shows him his newspaper ad promising that he works on contingency and doesn't demand money down, he immediately takes a marker and "rewrites" it to say that he does not work on contingency and expects money down. He also takes a moment to tear away the part about the state bar association and swallows it, implying that he's been disbarred.
  • Artistic License – Law: Played for Laughs; Hutz's actions frequently go below even what someone with no legal training would think to try. This has included blatant violations of protocol and mixing up or flat-out forgetting basic terminology. He's also implied to have been disbarred, which means he practices law without a licence.
  • Cloud Cuckoolander: He has shades of it, including contradicting himself mid-sentence and at one point forgetting what a lawyer is.
  • Characterization Marches On: In his first appearance, he was a skilled lawyer with unconventional and unethical methods. Later on, he tends to be completely hopeless.
  • 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 continued to have speaking roles in the comics.
  • Drop-In Character: By some accounts, the writers really liked Phil Hartman, and so would use any excuse to have Hutz (or Troy McClure) show up in an episode so Hartman could record with them. There are a lot of episodes where Hutz pops in, delivers one or two lines, and pops out.
  • 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!
    • When the Simpsons fought for Bart's custody because Burns took him in as an heir, they not only lost, but somehow Judge Snyder ended up convinced that Burns was Bart's biological father.
      Marge: We need to stop hiring him as a lawyer.
  • Evil Lawyer Joke: He's a walking dispensary of them, especially after he evolved from 'quirky but competent' to Chaotic Stupid.
  • Foil: His incompetence and buffoonery make him a significant contrast to the Blue-Haired Lawyer, who is way more competent and a stickler towards defending copyright.
  • Frivolous Lawsuit: His usual thing. Heck, he once sued the makers of The Never Ending Story for false advertising, when a movie that actually lived up to that title would logically never finish production.
  • Jerkass: He's greedy, unethical, treats people like dirt and has zero positive traits. The main things keeping him out of Hate Sink territory are that he's too incompetent to do anything actually harmful and that his ineptitude makes him a very hilarious character.
  • Never Needs Sharpening: During his final showing as a real-estate agent in "Realty Bites", he provided a pretty textbook case of using misleading slogans to spin flaws as positives.
    Marge: It's awfully small.
    Hutz: I'd say it's awfully "cozy."
    Marge: That's dilapidated.
    Hutz: "Rustic."
    Marge: That house is on fire!
    Hutz: "Motivated seller."
  • New Jobs As The Plot Demands: He's been seen assuming other jobs such as a real estate salesman, a shoe repairman, a talent agent, and a babysitter. Sometimes this is because most of his clients end up losing their houses (which prompted his move into real estate) and other times it's because he's been disbarred...again.
  • 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.
  • Out of Focus: Even before Hartman's characters were retired, Hutz's presence in the series was starting to majorly taper off after season 6. In season 7, he represents Lampwick in "The Day The Violence Died," but other than that, he has only two disposable cameo appearances. Afterward, he has absolutely no appearances in Season 8 (other than two background shots), and then in Season 9, he has an appearance in "Lisa the Skeptic" and then his spotlight episode "Realty Bites." After that, his character was retired and never mentioned again. This is not to say Hartman was phased out of the show before his death — Troy McClure's presence actually increased in seasons 7-9.
  • Perpetual Poverty: Still keeps up his law firm business, despite being on constant hard times and having few real successes. In one episode, Homer hires him on to babysit Bart, Lisa and Maggie for eight dollars a night and two popsicles out of the freezer (and he gets to keep the broken birdcage he found when rummaging through their trash), which he considers a good deal. He's also branched out into other fields such as talent representation, shoe repair and real estate, the latter of which was a natural step since most of his clients end up losing their houses.
    "Oh, sure. Like lawyers work in big skyscrapers and have secretaries. Look at him. He's wearing a belt. That's Hollywood for you."
  • 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.
    • A more minor case, but when Chester J. Lampwick sued Itchy & Scratchy Studios for stealing Itchy from him, except the film that could prove it was already destroyed by accident with no other copy available, Hutz asks the if the defendants had a copy of theirs. While it's depicted as another one of his dumb moments, in a real-life trial, Hutz would in fact be allowed to ask that, and if the studio actually had one, they would be required to turn it over.
  • Starting a New Life: In "Marge on the Lam", he attempts this for uncertain reasons, burning his belongings and declaring that his name is now Miguel Sanchez. The narration at the end of the episode suggests that this isn't the first time.
  • Still Got It: He says this about his negotiating skills when Homer hires him as a babysitter, even though he agreed to all of Homer's terms and the only "concession" he got was Homer letting him keep an old broken bird cage.
  • Ultimate Job Security: Frequently lost his cases, but kept getting hired by Homer and Marge regardless. He may just be the only lawyer they can afford. Lampshaded:
    Marge: You know, we should really stop hiring him.

    The Blue-Haired Lawyer 
https://static.tvtropes.org/pmwiki/pub/images/blue_haired_lawyer.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.
  • Laser-Guided Karma: While on the show he rarely, if ever, suffers any misfortune (besides the time Skinner kicks his ass), the comics have him suffer a little more.
    • Once, when pointing out Krusty would face no consequences for framing Homer on account of being a celebrity, Homer pies him in the face, to much rejoicing.
    • When he tries to sue Kent Brockman on behalf of Gomer Pyle for declaring "shazam", he is then counter-sued by Captain Marvel and his lawyers.
  • No Celebrities Were Harmed: The writers say 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. In merchandise, he was previously referred to as "Burns' Lawyer", because he was originally seen as a member of Mr. Burns' team of lawyers, before he represented other characters.
  • 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.
  • Skewed Priorities: One comic had him protest using the Birthday Song in order to put out a fire at an amusement park. He collapses from smoke inhalation right afterwards.
  • 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.

Police

    Chief Clancy Wiggum 
https://static.tvtropes.org/pmwiki/pub/images/wiggum_0.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.


  • Acrofatic: Like Homer, he can be surprisingly quick on his feet at times, catching up with and tackling Snake after a car crash and later managing to do a front flip off a roof even though he messed up the landing and got hurt.
  • 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.
  • Ambiguously Bi: He is clearly married to a woman and that Ralph is his son, but he has some questionable subtext with his partner, Lou. He also seemed to be attracted to Peter and Homer during their carwash sting operation in the crossover. He also uttered this line in "Homer Alone" after being kissed repeatedly by Homer for finding Maggie:
    Chief Wiggum: (chuckles) Just don't let it happen again, ya big lug.
  • A-Team Firing: Generally speaking, Wiggum couldn't hit the broad side of a barn. "Wiggum, PI" has him unload what has to be a dozen shots into an alligator at point-blank range, and miss every single one. Considering his gun safety record, his aim is probably the only reason he's still alive.
  • 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 to 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.
  • Big Eater: He has an appetite that can rival Homer's. In one episode, he is walking out of a sandwich shop with a sandwich so massive that he needs the assistance of Lou and Eddie to help it to the car.
  • 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: A few episodes like "The Blunder Years" and "Pranksta Rap" reveals that if he's motivated enough, he can make some great police work.
  • Character Catchphrase: Played with in "Behind the Laughter", in which he claims to have one.
    Chief 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.
  • Cloudcuckoolander's Minder: The only times he's ever portrayed as relatively intelligent is when he's interacting with Ralph.
  • 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. And also he causes more trouble for Springfielders than he solves it.
  • Donut Mess with a Cop: Loves them so much he'll merrily sing "Donuts, I got donuts" crossing the street after having just bought them.
  • 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.
  • The Dragon: He is often used by corrupt politicians and corporates to enforce their own interests over Springfield.
  • Dumb Ass Has A Point: In Lisa's Date With Destiny, he shoots the Autodialer machine in Homer's house because it was driving him crazy. He's called out on it but, if the scam went any further, SOMEONE else would have done it.
  • Early Installment Character-Design Difference: During the show's first two-and-a-half seasons, he had black hair, turning blue halfway through the third season.
  • Even Evil Has Loved Ones: In spite of his corruption he shows a lot of genuine affection for his son, Ralph and wife, Sarah.
  • 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, which in real-life terms would put him around the 400lb mark, nearly twice Homer's stated weight, and his underwear has to be made in a Norwegian town) and one of the dumbest.
  • Fat Slob: Big eater and out of shape.
  • Flanderization: In earlier seasons, he was the no-nonsense head of a highly-corrupt police department (even though he was liable to join in from time to time). As the SPD became a three-man force however, his intelligence (not that high to begin with) took a drop, essentially becoming a lapdog to Quimby, enforcing whatever dumb/heavy-handed law the mayor came up with.
  • Frontline General: As Wiggum himself points out, he's an unusual instance of a Chief of Police (roughly equivalent to Commissioner) that goes out on the beat.
  • Genre Savvy: The name of the Retirony trope comes from him 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 Javert: Sometimes (example being when he arrested Sideshow Bob for being an accomplice to his brother trying to destroy Springfield Dam, even when Lisa and Bart are there to tell him that Bob saved Springfield). Overall, he is just way too eager to arrest first and make investigations never.
  • 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 antibiotic bomb that destroyed Burns' germ lab also 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 tendency to do this — so much so that he provides the page image.
    Chief Wiggum: (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.
  • The Lopsided Arm of the Law: Either because the town of Springfield is a loony enough place to have a law warranting that much overkill or because Wiggum is indulging on his capacity to call on said overkill freely as the Chief, it's typical to see Wiggum barging into anybody doing even the most minor of peccadilloes with a gun and a quick ticket to the slammer, and conveniently leaving the bigger and nastier crimes alone.
  • Military Moonshiner: Season 5's "Marge on the Lam" depicts Wiggum stumbling upon Homer after emerging from his private alcohol refinery.
    Chief Wiggum: 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.
  • No Celebrities Were Harmed: Mixed with Vocal Evolution, originally his voice was an impression of David Brinkley that morphed into Edward G. Robinson when Hank Azaria was asked to talk faster. "The Day The Violence Died" has Roger Meyers Jr. outright point this out.
  • Oddly Small Organization: Although other members are sometimes seen, a couple episodes have jokes that the Springfield Police Department only has three members. (The others could be on reserve duty such as filing paperwork or overseeing community service.)
  • Officer O'Hara: "In the Name of the Grandfather" all but outright states that he's of Irish ancestry and that's why he's a police officer. However, this is pretty much the only time it comes up.
  • Pet the Dog: Is generally shown as being a patient and caring (if not entirely competent) parent to Ralph, and helped Mona Simpson escape the cops as a thank you for (unintentionally) helping to cure his asthma.
  • Police Are Useless: The poster trope. Just see all the examples posted on the trope page. He has a few competent moments, but these are far and between.
  • Police Pig: He's been called a pig for more than just being a cop. Naturally, the show has often lampshaded this, to the point of having him appear as an actual Pig Man in "Treehouse of Horror XIII" and "Marge Gamer".
    Chief Wiggum: Sideshow Bob has no decency! He called me "Chief Piggum!"
  • Real Men Wear Pink: "Marge on the Lam" shows him to be a fan of Lesley Gore's "Sunshine, Lollipops and Rainbows", jamming to it even while he's in the middle of a car chase.
  • 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.
  • Schiff One-Liner: Wiggum's obsession with giving the people he arrests a nickname is attached to an obsession to give them a "you did the crime, you're doing the time!" one-liner.
  • Smart Ball: He has his moments. "Who Shot Mr. Burns: Part 2" focuses on him doing fairly competent investigation work (which ends with him arresting the wrong person, but for understandable reasons) and "Mother Simpson" even has him Obfuscating Stupidity in order to help Mona escape the police.
  • Stripper/Cop Confusion: Went along with it for the money.
  • Suspect Is Hatless: He uses this exact sentence in "Homer's Triple Bypass".
  • Sympathetic Inspector Antagonist: Sometimes, when played sympathetically.
  • Throw the Dog a Bone: In his own, weird way, as the end of "Lisa the Iconoclast" he refuses to stop Homer when he seizes the role of town crier from Ned by force, simply because he feels Homer's much better.
    Wiggum: Let 'im march, boys. Let the man march.
  • Trademark Favorite Food: Donuts and coffee.
  • 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.
  • We Used to Be Friends: Was part of a barbershop group with Homer, Apu and Skinner, but they kicked him out before rebranding to the B-Sharps on their agent's advice. Wiggum's still quite sore about it.
    Lou: (seeing the B-Sharps performing) Is that nice, chief?
    Wiggum: It sure is, Lou, it sure it. Get the tear gas.

    Sergeant Lou and Officer Eddie 
https://static.tvtropes.org/pmwiki/pub/images/lou_and_eddie.png
Lou (left) and Eddie (right).
Debut: "There's No Disgrace Like Home"
Voiced by: Hank Azaria (Lou, 1990-2020), Alex Désert (Lou, 2021-present), Harry Shearer (Eddie).
Chief Wiggum's seconds-in-command.
  • Ambiguously Bi: When Wiggum tells Eddie to direct traffic because he's the most graceful, Eddie makes flamboyant gestures while doing so and Wiggum comments "And that guy can't find a girlfriend, I'll never figure it out." However, Eddie is also mentioned to have slept with Lou's ex-wife.
  • 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.
  • Character Catchphrase: Lou says, "Uh, Chief?"
  • Characterization Marches On: Lou goes from nasty cop to Wiggum's retainer. Likewise, Eddie becomes The Quiet One.
  • Cloudcuckoolander's Minder: Lou becomes this to Wiggum in later seasons, as he often contradicts him when the latter says something stupid.
  • 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.
  • Early Installment Character-Design Difference: Lou appeared as yellow in early episodes.
  • 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.
  • Out of Focus: Eddie, initially half of a duo with Lou, began to be seen less and less with Lou being more typically presented as Wiggum's Sidekick. The 2018 episode "Homer is Where the Art Isn't" states that economic troubles forced Springfield to lay off a third of its police force, that third being Eddie.
  • Pet the Dog: Though often seen as corrupt, snarky or ineffectual, they are genuinely supportive of Bart's aspirations of becoming a police officer.
  • The Quiet One: Eddie is usually quiet, though he used to be a bit more choppier and talked more than he does now.
  • 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.
  • Vomiting Cop: When the three encounter Comic Book Guy and Agnes Skinner in bed, Eddie hunches over and covers his mouth like he's about to vomit. Lou reassures him by saying, "It's okay, man. If it doesn't affect you, you're not human."

Criminals

    Robert Underdunk Terwilliger, Jr., Ph.D. (Sideshow Bob) 
https://static.tvtropes.org/pmwiki/pub/images/new_sideshow_bob_unlock_7.png

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 intellect, 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.


  • Advertised Extra: Despite his enormous popularity and being added to the HD version of the opening introduced in Season 20, he's to date only made significant appearances in 16 of the show's more than 750 episodes (two of them being Treehouse of Horror episodes), with a handful of brief cameos elsewhere. Justified, due to him being technically voiced by a recurring guest star.
  • Affably Evil: From time to time, he's portrayed in a more genuinely likable light. Of course, this doesn't stop him from being a ruthless criminal.
  • Animalistic Abilities: In "The Man Who Grew Too Much", Sideshow Bob reveals he's been modifying his own DNA and now has, among other things, the strength of a Brahma bull, the thighs of a grasshopper, and the sonar of a killer whale.
  • Anime Hair: He could be mistaken for a palm tree with the right dye.
  • Arch-Enemy: Bart Simpson is his primary arch-enemy. Krusty the Clown and rakes are also this.
  • Artifact Alias: 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 say 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. Lampshaded in "The Great Louse Detective", when he's introduced as the criminal being recruited to find Homer's attempted murderer. After Bart and Lisa scream "Aah, Sideshow Bob!", Bob answers "Oh, come now. We've been through so much together. Just call me 'Bob.'"
  • 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.
  • The Bad Guy Wins: In Treehouse of Horror XXXIV, although it's eventually subverted when he gets sentenced to prison for 30 years and later gets brutally mauled by Lisa.
  • Beautiful Singing Voice: He takes pride in his baritone, and sang old classics to good response when he temporarily hosted Krusty's show. Bart also says he has "such a beautiful voice", and while that was an attempt to distract him from killing him by convincing Bob to sing, in a later episode he says "the only thing he didn't need to genetically modify was his voice", implying the compliment was at least partly genuine. When Homer hears him sing an opera, he's hypnotized by the performance and calls it brilliant, enough to temporarily make him forget that Bob was trying to kill him.
  • Big Bad: Is often the main antagonist of whatever episode he has something big planned for the Simpsons or Krusty. He's also the villain of The Simpsons Ride, in which he hijacks the titular theme park ride in an attempt at the Simpsons' lives.
  • 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.
  • Body Horror: After having removed his own face in "The Bob Next Door", the show began to make a Running Gag of the fact that it was never completely sewed back on properly, and peels off at inopportune times.
  • Breakout Villain: In the first season, he was a minor character, but he's become one of the show's most iconic antagonists over the years, rivaled only by Mr. Burns. He's also one of the most well-known characters to not be played by an actual cast member.
  • The Bus Came Back: After a 4 year absence, Bob makes his return in Treehouse of Horror XXXIV.
  • But Not Too Bi: Claims to have experimented in college, 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 does claim to have Experimented in College; 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.
  • Celebrity Paradox: Marge: "A lot of people sound like Sideshow Bob, like Frasier on Cheers"
  • Character Catchphrase: "Hello, Bart". Alternative, there's the grumble he makes whenever he gets hit in the face with a rake.
  • Characterization Marches On: He was originally Krusty's non-speaking sidekick in early episodes.
  • Classically-Trained Extra: A Yale-educated thespian who started his career as Krusty's sidekick and designated target for lowbrow slapstick.
  • Complexity Addiction: He can't simply gut Bart with a knife.
  • Corrupted Character Copy: Bob is an homage to Kelsey Grammer's signature character Frasier Crane: like Frasier, he's a snobby, chronically unlucky Ivy Leaguer with a passion for the fine arts. The one big difference is that while Frasier's a caring psychiatrist, Bob's a homicidal maniac. note 
  • 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.
  • Disproportionate Retribution: Tries to nuke Springfield when Krusty refuses to abide by his "no television" ultimatum.
  • 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. It has the bonus of "Patiño" being an actual surname.
    • In Czech he is known as "Levák Bob" which means crook (or 'left-handed').
  • 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 (though his only crime at that point was framing Krusty for armed robbery in retaliation for years of being treated like garbage, and his sob story did make him seem repentant), 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 three timesnote . 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.
    Sideshow Bob: Rakes. My old archenemy.
    Bart: I thought I was your archenemy.
    Sideshow Bob: I have a life outside of you, 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.
    • He seemed to be genuinely fond of Selma while they were dating, and he didn't figure out about her inheritance until the day before their wedding, so he couldn't have been plotting her murder before that point. It's implied that he loses any affection he had for her when he has to watch an episode of MacGyver.
  • Even Evil Has Standards:
    • Sideshow Bob 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.
    • While helping Homer to find and stop a person (later revealed to be Frank Grimes Jr.) making a few attempts to kill him, Sideshow Bob is shocked when he finds out Homer makes too many enemies in his life so far.
  • Evil Brit: Mistaken for this (multiples times out of universe and at least once in-universe) due to his accent, but he doesn't use any British terms or slang and states he's American multiple times. He actually has a Mid-Atlantic accent, which most viewers don't recognize because it's effectively extinct nowadays.
  • Evil Genius: A manipulative, Yale-educated psychopath.
  • Evil Is Hammy: Can't resist gloating or being the center of attention. This is a big part of his Fatal Flaw, as he often ends up foiling his own plans in an attempt to show off somehow.
  • Evil Is Petty:
    • Threatens to nuke Springfield because he finds television too lowbrow, and genuinely tries to do so when Krusty hijacks the emergency broadcast channel when it becomes the only channel left on the air.
  • Evil Laugh: He does evil laughs fairly often. They're usually low and menacing, but sometimes get higher and more deranged. Justified because he's a Wicked Cultured villain who enjoys theater, so of course he would be melodramatic enough to do this.
  • Eviler than Thou: His brother Cecil, who nearly kills the entire town by blowing up a dam, which even Bob was willing to pull a Heroic Sacrifice to stop (though Bob had previously tried to nuke Springfield at that point). 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.
  • Expy: The producers liken him to Wile E. Coyote, a “super genius” that’s often undone by A) being Too Clever by Half and B) regularly facing off against a talented Trickster character.
  • 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-year-old boy nonetheless.
  • Feuding Families: Over the course of the series he's dragged his entire extended family into his grudge against the Simpsons to the point that it's effectively a family feud.
  • 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.
  • From Nobody to Nightmare: Starts off as Krusty's silent, abused sidekick. Becomes a genuine criminal mastermind and psychopath who never fails to terrify the Simpsons simply by showing up.
  • 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.
    • While he hated the indignity of being the put-upon sidekick, when Krusty erased all those old episodes, Sideshow Bob vowed revenge for him erasing his past.
  • Heel–Face Revolving Door: He tends to go back and forth between trying to kill people and turning his life around.
  • Hereditary Hairstyle: He inherited his hair from his mother, which he then passed on to his son.
  • Hidden Depths: While he considers himself an exemplar of high culture and is snobbish towards works he perceives as lowbrow like Krusty's slapstick or MacGyver, he doesn't fall into the "fantasy ghetto" given that he makes a Harry Potter reference at least once.
  • Honor Among Thieves: Bob has been consistently shown to get along with Snake when they're cellmates.
  • 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.
  • Laser-Guided Karma: His murdering of Bart in the Ei8ht segment of Treehouse of Horror XXXIV eventually leads to Lisa murdering him as revenge, which also doubles as a Karmic Death.
  • 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.
  • Mistreatment-Induced Betrayal: His initial descent into villainy was because of years of crummy treatment under Krusty.
  • Medium Awareness: Consistently displays knowledge of the show's Comic-Book Time. For example, in season 8's "Brother From Another Series", he tells Edna that he hasn't been on a date in six years, referring to his dates with Selma back in season 2's "Black Widower" - even though the age of all the child characters makes it clear that nowhere near six years has passed in-universe. In "Treehouse Of Horror XXVI" he notes that he's spent 24 years trying to kill Bart.
  • 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.
  • No Celebrities Were Harmed: His voice actor, Kelsey Grammer, has stated that Bob's voice is based on the actor and director Ellis Rabb.
  • Odd Friendship: With Snake. The two are often cellmates and will usually hug each other when one or both are released.
  • Omnicidal Maniac: Not usually, but he's more than willing to destroy all of Springfield in "Sideshow Bob's Last Gleaming" when he wasn't able to completely eliminate television.
  • Pay Evil unto Evil: Most of the people Bob targets are odious enough to deserve his ire, even if he takes immoral and murderous extremes to take them down. Krusty was a sleazy Mean Boss (a trait he continues with any of Bob's replacements), Selma was a repugnant spouse, Quimby is an incompetent and corrupt mayor that, even with Bob's own unscrupulous activities, he could have easily done a better job as. Even Bart is a relentless often mean spirited prankster who, after laughing uproariously at Krusty's onscreen abuse of Bob, fails to comprehend why Bob would have ever wanted to betray his hero. It has been lampshaded more than once that several people that Bob tried to murder, most of Springfield wanted to do so themselves.
  • 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 the 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!"
  • Psycho Knife Nut: As time goes on and his sanity degrades he's developed a fondness for kitchen knives as shown by the picture above.
  • Reformed, but Rejected: Sideshow Bob really tried to live an 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!
  • Renaissance Man: 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 in literature and philosophy.
  • Sadist: He always tries to kill Bart with 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.
  • Say My Name: Often whenever he appears, at least Bart and Lisa and maybe the rest of the Simpsons will say, "AAAAAAAHHHH!!! SIDESHOW BOB!!!!" However, in "Day of the Jackanapes", when Bart first sees him, he just says, "Oh, it's you, Bob," since he pretty much knows he will end up in jail again.
  • 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 an 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 5,000 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.
    • Bob's brother, Cecil, is played by David Hyde Pierce, and his father, Bob Sr., is played by John Mahoney. Pierce and Mahoney starred alongside Kelsey Grammer in Frasier as Fraiser's brother and father, respectively.
  • Silver Tongue: Can play any crowd with just a few words. Best shown in "Brother From Another Series", where a mob gathered to protest his release goes from calling for his blood to loving him in about ten seconds. In "Black Widower" he even fooled otherwise skeptical characters like Lisa that he had truly reformed.
  • 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. However, he is capable of empathy and love and his likeable personality is genuine. Bob's also far more openly emotional than your average psycho.
  • 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.
  • Straight Edge Evil: When he gets married to Selma, he tries to convince her to give up smoking. Apart from the occasional glass of wine he seems to have no vices himself.
  • 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 a program he deems more beneficial for its child viewers, by introducing them to high culture and educational and emotional concepts above the usual level of their age. It actually pays off, with his show receiving a good reception from the kids and getting record-high ratings. Until Bart reveals what he did, of course. Still, even from prison, he won an Emmy for his role.
  • White Anglo-Saxon Protestant: Fits all the criteria with the exception of his religion being unknown. He's of English ancestry, a native of New England, comes from Blue Blood (his mother is a theater actor and his father is a medical doctor), attended an Ivy League school, considers himself an exemplar of high culture, and has a Mid-Atlantic accent (making him stand out as very out of place in modern Springfield).
  • 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, even if he has openly expressed apathy in committing any sort of rivalry with her.
  • 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_61.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 Motif: He's themed around snakes, as shown by his name, alias, tattoo and car decoration of a cobra. In Marge Gamer, his in-game avatar is a snake and he even dresses as a snake in Revenge Is a Dish Best Served Three Times.
  • 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!
  • Character Catchphrase:
    • "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.
  • Depending on the Writer: Depending on the episode, he can be anywhere from a petty thief to a legitimately dangerous armed criminal. Also, like Homer his strength and toughness varies. Sometimes he's able to restrain a man of similar size with one arm, but a few episodes had him being beaten up by Homer with little to no effort.
  • 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.
    • Not leaving out when he threatened to murder the entire Simpson family in the Simpsons' own home just because he had a tune stuck in his head after deciding not to rob them.
  • 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.
  • I Have Many Names: His aliases have included Chester "Snake" Turley, Snake Jailbird, Albert Knickerbocker Aloysius Snake. As a teenager, he was called "Detention Bird", and as an archaeologist, he was Professor Jailbird.
  • I Shall Taunt You: He knows from long experience how incompetent the cops in Springfield are so he usually takes a moment to mock them before fleeing.
  • 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 counseling.
    Snake: Sometimes it feels like, when I rob you, that you're not even there.
    Apu: That's because you are also robbing my brother Sanjay.
  • Mr. Fanservice: He's quite muscular and the show used to draw attention to this by having him pose topless or taking part in calendar photos.
  • Odd Friendship: With Apu, Snake robs him multiple times but the two are shown interacting with each other outside of work. When Snake gets a job, Apu tries to rob him instead but Snake talks him down.
    • With Sideshow Bob, Sideshow Bob is well-spoken, snobbish, and looks down on things he considers low-brow, while Snake talks like a valley boy and enjoys things like Rock music and partying. Snake is a Punch-Clock Villain who's a pretty nice guy when not committing crimes while Sideshow Bob's crimes are very much personal. And while in prison Snake is usually an Alpha Bastard amongst the inmates while Sideshow Bob is The Friend No One Likes, to spite all this they get along quite well as cellmates and share a sincere hug before both of their parole hearings.
  • 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. When he was 13, he attended the same high school as a 16-year-old Chief Wiggum (who is canonically 43 years old). Meaning that Snake is 39-41 years old, but other sources claim he's 43 as well.
  • 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.
  • 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!
  • Surfer Dude: He speaks with a "Valley Boy" accent.
  • 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.
  • Villains Out Shopping: Sometimes he just hangs 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"

Day-to-day head of the Springfield Mafia. Voiced by Joe Mantegna.

According to the episode Donnie Fatso, Fat Tony died and was replaced by his identical cousin. Like Armin Tanzarian and Snowball II's death, don't expect this to come up again.


  • Affably Evil: Despite being a ruthless mafia leader who has committed almost every crime under the sun, he's a genuinely polite person and is on good terms with most of the Simpson family, especially Marge. He's even part of the carpool that the Simpsons kids are part of.
  • Ambiguously Bi: 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 the writers expected to appear only once, but kept coming back.
  • Back Up Twin: In Donnie Fatso, Fat Tony died and his cousin Fit Tony, who was identical in every way but build, took his place. Fit Tony quickly becomes Fat Tony due to overeating, essentially bringing Fat Tony back to life.
  • Cerebus Rollercoaster: Fat Tony does have his moments as a legitimate and serious threat in Springfield as he almost murdered Homer for being a police officer, he uses Bart as a scapegoat when the police arrested him for suspicion of murdering Principal Skinner, and he almost killed Homer and Marge after they refused to pay him for aiding the pretzel business.
  • Characterization Marches On: He had a thick Bronx accent in his first appearance.
  • Cultural Translation: In the Italian dub, he, appropriately enough, has a Sicilian accent.
  • The Don: He's not — that title belongs to Don Vittorio, to whom Tony is The Dragon — but because the latter shows up so infrequently, Tony basically fulfills the role most times The Don would appear in a story, and thus can be mistaken for one.
  • 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.
    • He was devastated by his father's death.
  • Even Evil Has Standards: There's one crime that Fat Tony the Second would never commit. Pickpocketing. The reason why is his father died because he needed a heart transplant, and the donor's heart was pickpocketed away.
  • 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."
  • Fat Bastard: Downplayed on the "bastard" part in that he's Affably Evil. As for the "fat" part, it's in his nickname.
  • Formerly Fit: How Fit Tony became an Identical Cousin. In the comics Fat Tony has apparently been gaining weight his whole life, as he used to be called Thin Tony before becoming just Tony.
  • Iconic Sequel Character: One of the supporting characters who didn't appear in the first season, as he's introduced in season 3.
  • 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.
  • The Mafia: He runs Springfield's mafia.
  • Meaningful Name: "D'Amico" roughly means "of friends" in Italian. Mafiosos 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.
  • Not Me This Time: In "The Fat Blue Line" He is framed for pickpocketing and Wiggum has to get him off.
  • 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.
  • Pietà Plagiarism: The original Fat Tony, in the arms of Homer.
  • 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 and is a self-described "patron of the lively arts". He always dresses well and his home is classically styled and furnished.

    Legs and Louie 
Debut: "Bart the Murderer"

Fat Tony's associates. Voiced by Harry Shearer (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.
  • Evil Counterpart: To Lou and Eddie, they either are or may as well be the only members of Fat Tony's gang as Lou and Eddy are the only cops besides Chief Wiggum. Louie in particular has a similar name to Lou and will either be Those Two Guys with Legs or part of a Straightman And Wiseguy due with their boss, depending on the needs of the episode.
  • Expy: Of Goodfellas Frankie Carbone, according to the latter's actor (who unsuccessfully sued The Simpsons's producers).
  • Hidden Depths: Louie can be seen attending the same rock'n'roll camp as Homer.
  • Mooks: Of Fat Tony.

    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, often being shown as part of Fat Tony's entourage alongside Legs and Louie .
  • The Comically Serious: The entire joke with this guy is that he's stoic and refuses to say anything useful even when it's counterproductive. In one scene, he insists there's a good reason for an assailant on him to not shoot him, but also that he refuses to spill the beans on why.
  • 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!"
  • Everybody Has Standards: Despite his hatred of squealing and generally unhelpful nature, he's the one who tells Louie his mother's pasta sauce comes from a can.
  • Foil: To Frankie the Squealer.
  • Laughably Evil: His attempts to maintain silence, even when he ought to speak up, make him humorous.
  • 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', an apt name for a guy who says very little. His real name is Giovanni Silencio, which fits his Terse Talker persona as well.
  • The Starscream: In the episode "The Fat Blue Line", he framed Fat Tony for serial pickpocketing which is what finally got him arrested. This resulted in Johnny Tightlips taking over the mob, until he was caught by Chief Wiggum and Fat Tony working together.
  • 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?
      Johnny: I see a lot of things!
      Fat Tony: You know, you could be a little more helpful!
  • Stupid Evil: As seen the above dialogue, sometimes he keeps quiet when he really shouldn't.
  • Terse Talker: His lips are known to not loosen much.

    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 due to Homer killing the Grim Reaper and temporarily prevented everyone from dying, 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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