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* TheAce: 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.
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* EvenEvilHasStandards: He once abandoned a telemarketing scam because he doesn't like bothering people at home.
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* ArtisticLicenseLaw: A RunningGag is that he'll claim copyright infringement over things that are in the public domain, like Christmas carols. One halloween episodes has him making a solid legal document that would allow Burns to hunt people.
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* ArtisticLicenseLaw: A RunningGag is that he'll claim copyright infringement over things that are in the public domain, like Christmas carols. One halloween episodes Hhalloween episode has him making a solid legal document that would allow Burns to hunt people.
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* TooDumbToLive: In the Halloween episode above he is shot right after giving the document that makes it legal for Burns to kill him.
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* TooDumbToLive: In the Halloween episode above above, he is shot right after giving the document that makes it legal for Burns to kill him.
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* VillainousRescue: Has saved the lives of Bart and Lisa in "Brother From Another Series" and Homer in "Day of the Jackanapes"
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* VillainousRescue: Has saved the lives of Bart and Lisa in "Brother From Another Series" and Homer Series", Krusty in "Day of the Jackanapes"Jackanapes", and Homer in "The Great Louse Detective."
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* HadToComeToPrisonToBeACrook: 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.
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* CorruptPolitician: A massively over-the-top example. In fact, the mayoral motto is ''Corruptus in Extremis''.
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* SinsOfOurFathers: Bob is willing to kill Maggie in "The Italian Bob" just because she's a Simpson.
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* YouWillBeSpared: Has outright stated he is only interested in killing Bart. Has lampshaded his apathy towards Lisa on several occasions, even when she is the one who stops him. Bart will ''always'' be his ArchEnemy. Although after they ruined his life in Italy he declares vendetta on the whole family but future episodes shows that he still want Bart dead first and the family has acceptable targets.
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* YouWillBeSpared: Has outright stated he is only interested in killing Bart. Has lampshaded his apathy towards Lisa on several occasions, even when she is the one who stops him. Bart will ''always'' be his ArchEnemy. Although after they ruined his life in Italy he declares vendetta on the whole family (yes, including Maggie) but future episodes shows that he still want Bart dead first and the family has acceptable targets.
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Chief Wiggum's second-in-commands. Voiced by Creator/HarryShearer and Creator/HankAzaria.
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Chief Wiggum's second-in-commands. Voiced by Creator/HarryShearer Creator/HankAzaria and Creator/HankAzaria.
Creator/HarryShearer.
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* StoutStrength
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* OddFriendship: With Snake, the two are often cellmates and will usually hug each other when one or both are released.
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* VillainousRescue: Has saved the lives of Bart and Lisa in "Brother From Another Series" and Homer in "Day of the Jackanapes"
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* EvenEvilHasLovedOnes:
** In "The Mook, The Chef, The Wife and her Homer" he explains his wife was [[BusmansVocabulary "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 he starts to sympathize with him.
** His son/nephew Micheal even though [[IAmNotMyFather their relationship]] [[OverlordJr has problems]] he clearly loves his son and after his death [[MySiblingWillLiveThroughMe his cousin]] [[ParentalSubstitute seems to have taken him in.]]
** Fat Tony and Fit Tony were this to each other demonstrated by the picture he showed Homer upon introduction.
** In "The Mook, The Chef, The Wife and her Homer" he explains his wife was [[BusmansVocabulary "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 he starts to sympathize with him.
** His son/nephew Micheal even though [[IAmNotMyFather their relationship]] [[OverlordJr has problems]] he clearly loves his son and after his death [[MySiblingWillLiveThroughMe his cousin]] [[ParentalSubstitute seems to have taken him in.]]
** Fat Tony and Fit Tony were this to each other demonstrated by the picture he showed Homer upon introduction.
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* FormerlyFit: How Fit Tony became an [[UncannyFamilyResemblance Identical Cousin.]]
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* StoutStrength
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* InspectorJavert: Sometimes.
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* AffablyEvil: In more recent seasons.
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* EvilBrit
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* EvilRedhead
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[[center: [- [[Characters/TheSimpsons Main Character Index]] | [[Characters/TheSimpsonsTheSimpsonFamily Simpson Family]] |[[Characters/TheSimpsonsElementarySchool Springfield Elementary School]] | '''Government, Judges and Lawyers, Police and Criminals''' |[[Characters/TheSimpsonsNuclearPowerPlantShopkeepers Springfield Nuclear Power Plant, Springfield Shopkeepers]]| [[Characters/TheSimpsonsChurchDoctorsCelebrities First Church of Springfield, Doctors, Celebrities]] | [[Characters/TheSimpsonsFriendsNeighborsFamilies Friends and Neighbors, Families]] |[[Characters/TheSimpsonsOtherRecurringCharacters Other Recurring Characters]] | [[Characters/TheItchyAndScratchyShow Itchy & Scratchy Characters]] | [[Characters/TheSimpsonsOneTimeCharacters One-time Characters]]]]-]
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----
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** JerkassHasAPoint: That being said she does rightfully call out Homer for being a bad father.
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** PhraseCatcher: "AAAAAH! Sideshow Bob!"
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* TheMafia
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* PermaStubble
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* VillainsOutShopping
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* TerseTalker
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* TerseTalkerTerseTalker: His lips are known to not loosen much.
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* ButtMonkey: Whenever Lou raises minor objections, he will usually get chewed out for it by Chief Wiggum.
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* ButtMonkey: Whenever Lou raises minor objections, he will usually get chewed out for it complaining by Chief Wiggum.
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* ShoutOut: He and his father, Dr. Robert Terwilliger, Sr., are mistakenly believed to be named after Dr. Terwiliker from Film/The5000FingersOfDrT; their actual namesake is Terwiliger Boulevard in Portland, Oregon, the hometown of Creator/MattGroening.
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[[folder:Sergeants Eddie and Lou]]
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* ButtMonkey: Whenever Lou raises minor objections, he will usually get chewed out for it by Chief Wiggum.
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[[folder: Robert Underdunk Terwilliger, Ph.D. (Sideshow Bob)]]
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[[folder: Robert Underdunk Terwilliger, Jr., Ph.D. (Sideshow Bob)]]
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* AffablyEvil: He's usually rather polite and comedic...though he's a psychopath nonetheless.
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* AffablyEvil: He's usually rather polite and comedic... though he's a psychopath nonetheless.
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that's just parodying the vomiting cop trope
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* AmbiguouslyHuman: Lou was about to vomit after seeing Agnes Skinner and Comic Book Guy in bed together but Eddie says "It's okay, man. If it doesn't affect you, you're not human." .
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* FlatCharacter: 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.
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* RaceLift: Eddie was yellow in earlier episodes but is now black.
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* RaceLift: Eddie Lou was yellow in earlier episodes but is now black.
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* KavorkaMan: He is the mayor what he looks like doesn't matter much
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* KavorkaMan: He is the mayor what mayor. What he looks like doesn't matter muchmuch.
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* ReallyGetsAround: Some are escorts other are mistresses.
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* ReallyGetsAround: Some are escorts other escorts, others are mistresses.
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* SleazyPolitician:
** In fact, he provides the image page 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 [[BlatantLies 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.
** In fact, he provides the image page 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 [[BlatantLies 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.
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* SleazyPolitician:
**SleazyPolitician: In fact, he provides the image page of this trope. 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 [[BlatantLies 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.
**
** 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 [[BlatantLies 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.
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* LegoGenetics: Gave himself superpowers by splicing his [=DNA=] with various animals. These abilities never show up again but the episode was implied to be AllJustADream that Flanders was having.
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* EarlyInstallmentWeirdness: He was originally Krusty's non-speaking sidekick in early episodes.
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* WantingIsBetterThanHaving: He decides not to kill Bart when he gets the chance as chasing him gives him something to live for.
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* ReplacementGoldfish: He died and was replaced by his cousin ''Fit Tony'', who then got fat and became the new Fat Tony.
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* IneffectualSympatheticVillain: Sideshow Bob frequently veers into this territory; indeed, despite his fame, he had never killed anyone. The poor guy can't even win against a rake.
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* IneffectualSympatheticVillain: Sideshow Bob frequently veers into this territory; indeed, despite his fame, infamy, he had has never killed actually succeeded in killing anyone. The poor guy can't even win against a rake.
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!Government
[[folder:Mayor Joe Quimby]]
[[quoteright:264:http://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 Creator/DanCastellaneta.
* UsefulNotes/AmericanAccents: Joe Quimby and his family speak in a broad UsefulNotes/{{Boston}} (Kennedy-esque) accent, humorously picked up on by Creator/JonStewart whenever he's discussing the Kennedys.
* CatchPhrase: "Vote Quimby!"
* EveryoneHasStandards:
** Despite his ways, he does have his limits like having a woman thrown in jail for her nervous breakdown [[note]] In [[Recap/TheSimpsonsS3E15HomerAlone Homer Alone]][[/note]], and holding the town hostage for monetary reasons [[note]][[Recap/TheSimpsonsWhoShotMrBurns Who Shot Mr. Burns?]][[/note]].
** Though a huge womanizer, he was horrified at the idea of sleeping with his niece.
* FatIdiot: Though nowhere near as bad as Homer or Chief Wiggum.
* FutureLoser: Has lost his lofty political position and become a taxi driver in the hypothetical future episode "Lisa's Wedding."
* ITakeOffenseToThatLastOne: 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.
* KavorkaMan: He is the mayor what he looks like doesn't matter much
* MayorPain: {{Trope Namer|s}} for Type B. An outright corrupt, opportunistic, embarrassing, sleazy politician who couldn't care less for Springfield.
* NobleDemon: 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.
* NoCelebritiesWereHarmed: 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]]Sideshow Bob's campaign commercial scorning Quimby as soft on crime mimics the notorious Willie Horton ad deployed by Dukakis' 1988 opponent for U.S. President, UsefulNotes/GeorgeHWBush[[/note]]. Mrs. Quimby dresses like Jacqueline Kennedy.
* OverlyLongName: Joseph Fitzgerald O'Malley Fitzpatrick O'Donnell the Edge "Diamond Joe" Quimby
* PetTheDog: He was willing to sacrifice television if it meant stopping Sideshow Bob from detonating a nuke.
* ReallyGetsAround: Some are escorts other are mistresses.
* SleazyPolitician:
** In fact, he provides the image page 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 [[BlatantLies 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 [[CorruptPolitician 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.
* ScrewTheRulesIHaveConnections: When Marge suffered a nervous breakdown and blocks traffic on a bridge, she was arrested. Mayor Quimby immediately pulled some strings to get her released without charges, claiming that if she went to jail, he could kiss the "chick vote" goodbye.
* ScrewTheRulesIHaveMoney: When his nephew Freddy was WronglyAccused 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 HairTriggerTemper.
* TheStoner: Smokes pot, and even grows several plants in his office.
* StrawmanPolitical: As the series' most prominent recurring Democratic politician, he serves as the primary target for {{Take That}}s aimed at Democrats and liberals.
* VerbalTic: 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, Bart uses this verbal tic to trick Quimby into thinking he's his son.
* YourCheatingHeart: 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 [[Film/CitizenKane Charles Foster Kane did for his mistress, whose singing voice was good, but not good enough for opera]]).
[[/folder]]
!Judges and Lawyers
[[folder: Judge Roy Snyder]]
[[quoteright:211:http://static.tvtropes.org/pmwiki/pub/images/roy_snyder_official_image.png]]
-->Debut: ''"Krusty Gets Busted"''
Voiced by Creator/HarryShearer.
* AmbiguouslyBrown: His skin color has changed from yellow to brown repeatedly throughout the series to stay brown.
* BunnyEarsLawyer: A good judge for the most part, but has a strange preoccupation with a clown desk figurine.
* FirstNameBasis: 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.
* ReasonableAuthorityFigure: One of the few people with authority in Springfield who is (usually) characterised as competent, non-brutal, and non-corrupt.
* YourCheatingHeart: He admitted in court that his wife had left him, since then he has been seen with Lindsey Naegle.
[[/folder]]
[[folder: Judge Constance Harm]]
[[quoteright:320:http://static.tvtropes.org/pmwiki/pub/images/2054878_judge_constance_harm.png]]
-->Debut: ''"The Parent Rap"''
Voiced by Jane Kaczmarek
* CoolPet: Has a pet seal named Poncho that doubles as a guard dog, and ''barks'' like one.
* DisproportionateRetribution: A lot, such an 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.
* HangingJudge: To give one example of how harsh she can be, in one episode she retracted Homer's driving license for driving it 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 [[Series/MalcolmInTheMiddle Jane Kaczmarek]]. She enjoys creating cruel and unusual punishments for criminals in her court.
** JerkassHasAPoint: That being said she does rightfully call out Homer for being a bad father.
* PetTheDog: In the 300th episode she does grants Bart emancipation from his family, specifically ''Homer'', after his jerkass tendencies reaches new heights.
* MeaningfulName / NamesToRunAwayFromReallyFast: Harm's name is a pun on the phrase "Constant Harm," implying that she likes issuing cruel punishments to people in her courtroom.
* ReasonableAuthorityFigure: Subverted. While she has the appearance of a stern, no nonsense judge, she holds serious grudges against other people.
* {{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."
[[/folder]]
[[folder: Lionel Hutz]]
[[quoteright:250:http://static.tvtropes.org/pmwiki/pub/images/lionel_hutz917.png]]
-->Debut: ''"Bart Gets Hit by a Car"''
-->Final Episode: ''"Realty Bites"''
Voiced by: Creator/PhilHartman
* TheAlcoholic: As implied in "Marge in Chains." He even argued his case before the court and was then informed he wasn't wearing any pants. He's also seen drinking scotch at nine-thirty in the morning. In front of clients, no less.
* AmbulanceChaser: In "Bart Gets Hit By a Car," Homer says upon meeting him, "You were the guy chasing Bart's ambulance."
* BunnyEarsLawyer: Averted. He's eccentric, odd and sleazy. And really, really bad at his job. The rare times he does win a case, it's because of something Bart and/or Lisa did.
* ChuckCunninghamSyndrome: 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.
* FrivolousLawsuit: His usual thing. Heck, he once sued the makers of ''Film/TheNeverEndingStory'' for false advertising.
* MakeTheDogTestify: Does this occasionally.
* SmartBall: 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 will 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.
* UltimateJobSecurity: Frequently lost his cases, but kept getting hired by Homer and Marge regardless. Lampshaded:
-->'''Marge:''' You know, we should really stop hiring him.
[[/folder]]
[[folder: Blue-Haired Lawyer]]
-->Debut: ''"Bart Gets Hit by a Car"''
Voiced by Creator/DanCastellaneta.
* AmoralAttorney: Although unlike most examples, he isn't outright malevolent.
* ArtisticLicenseLaw: A RunningGag is that he'll claim copyright infringement over things that are in the public domain, like Christmas carols. One halloween episodes has him making a solid legal document that would allow Burns to hunt people.
* NoCelebritiesWereHarmed: WordOfGod says he's based on the appearance of actor Charles Lane and the voice and mannerisms of Roy Cohn.
* NoNameGiven: His actual name has never been revealed.
* TooDumbToLive: In the Halloween episode above he is shot right after giving the document that makes it legal for Burns to kill him.
* YouGottaHaveBlueHair: Has blue hair.
[[/folder]]
!Police
[[folder:Chief Clancy Wiggum]]
[[quoteright:180:http://static.tvtropes.org/pmwiki/pub/images/chiefwiggum_3943.jpg]]
->"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 Creator/HankAzaria.
* ArtisticLicenseGunSafety: 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.
* BadCopIncompetentCop: By himself, if he gets lucky or motivated enough to catch you he can be bribed anyway.
* BaitAndSwitch: 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.
* BrilliantButLazy: The episode "Pranksta Rap" reveals that if he's motivated enough, he can make some great police work.
* CatchPhrase: Played with in "[[Recap/TheSimpsonsS11E22BehindTheLaughter Behind the Laughter]]", in which he claims to have one.
-->'''Wiggum:''' N'yeah! Wah! Wah-wah-wah! No, I lost it.
* DirtyCop: He accepts (and often expects) bribes.
* DotingParent: 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.
* FatBastard: Apathetic, self-interested, and more than willing to abuse his authority for his own gain. [[PetTheDog He does love his son though]].
* FatIdiot: He is one of the fattest character and one of the dumbest.
* FatSlob: Big eater and out of shape.
* {{Flanderization}}: Was not such as incompetent in the first season. Wasn't really present either.
* GenreSavvy: Is the TropeNamer 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 days before he retires. … Which is actually a RunningGag regarding the Springfield Police Department's equipment.
* HiddenDepths: 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.
* InspectorJavert: Sometimes.
* InspectorLestrade: When Bart and/or Lisa play AmateurSleuth.
* IOweYouMyLife: 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.
* JugglingLoadedGuns: Has a frequent tendancy to do this.
-->''(on Homer)'' "Well, if it isn't that stupid cop from TV." ''([[HypocriticalHumor proceeds to scratch his ear with the barrel of his gun]])'' "Oh yeah, that got it."
* TheNicknamer: It seems like the only part of his job he's passionate about is coming up with cleaver names for the people he arrests.
* NobodysThatDumb: He tends to have these types of moments.
** In season 23 [[Recap/TheSimpsonsS23E14AtLongLastLeave "At Long Last Leave"]], after the Simpsons were banished from Springfield, Homer and Marge sneak back into Springfield under the disguise of Mr. Burns and Smithers. When Chief Wiggums first spots them, it appears that he fell 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.
* PoliceAreUseless: He has a ''few'' competent moments, but these are far and between. When Homer briefly replaces him as Police Chief and decides to quit, Homer takes off his badge and says he'll offer it to the next person he sees, which turns out to be Wiggum. He's amused because this was actually how he ''first'' got the job.
* SuspectIsHatless: He provides the {{Trope Namer|s}} in "Homer's Triple Bypass".
* StripperCopConfusion: Went along with it for the money.
* SympatheticInspectorAntagonist: Sometimes, when played sympathetically.
* YouGottaHaveBlueHair: Earlier in the show, he had black hair. Became blue as the show evolved in later seasons.
[[/folder]]
[[folder:Sergeants Eddie and Lou]]
[[quoteright:350:http://static.tvtropes.org/pmwiki/pub/images/simpsonsloueddie.jpg]]
--> Debut: ''"There's No Disgrace Like Home"''
Chief Wiggum's second-in-commands. Voiced by Creator/HarryShearer and Creator/HankAzaria.
* AmbiguouslyHuman: Lou was about to vomit after seeing Agnes Skinner and Comic Book Guy in bed together but Eddie says "It's okay, man. If it doesn't affect you, you're not human." .
* CatchPhrase: Lou says, "Uh, Chief?"
* NoCelebritiesWereHarmed: Hank Azaria based Lou's voice on Creator/SylvesterStallone.
* OnlyOneName:
-->'''Guy:''' Now what are your last names?
-->'''Lou:''' We don't have them. We're like Cher.
* OnlySaneMan: Zigzagged. Lou sometimes appears more competent than Wiggum, but he is also capable of being corrupt.
* TheQuietOne: Eddie is usually quiet, though he used to be a bit more chopsier and talked more than he does now.
* RaceLift: Eddie was yellow in earlier episodes but is now black.
* SaltAndPepper: Lou is the Pepper to Wiggum's and Eddie's Salt.
* ThoseTwoGuys: Though Eddie hardly ever speaks and it's Lou that gets the bulk of the characterization.
[[/folder]]
!Criminals
[[folder: Robert Underdunk Terwilliger, Ph.D. (Sideshow Bob)]]
[[quoteright:160:http://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 Creator/KelseyGrammer.
* AffablyEvil: He's usually rather polite and comedic...though he's a psychopath nonetheless.
* AnimeHair: He could be mistaken for a palm tree with the right dye.
* ArchEnemy: Bart Simpson and Krusty the Clown. And [[ArsonMurderAndJaywalking rakes]].
* ArtifactTitle: 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 said "Vote for Sideshow Bob" as opposed to "Vote for Terwilliger" or simply "Vote for Bob". The only time he ever seemed to get angry at the name was when he was 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 [[BerserkButton just made Bob scream in fury while he increases the speed of the plane]].
* AscendedExtra / EarlyBirdCameo: Bob first appears as a silent background character in "The Telltale Head".
* AxCrazy: He started to qualify for this when his attempts to kill Bart included trying to have him cremated alive and when he visibly removed his cell mate's face and cut off his own. He also ties up Bart while singing casually about wanting to gouge out Bart's eyes. And then there's the Treehouse of Horror XXVI segment "Wanted: Dead, Then Alive" which has several moments that are genuinely disturbing.
* BigBadEnsemble: 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.
* BiTheWay: He off-handedly mentions experimenting during college when Homer is surprised that he has a wife.
* CardCarryingVillain: He's an EvilGenius and he's ''not'' particularly modest about the fact, either.
* CatchPhrase: "Hello, Bart".
** PhraseCatcher: "AAAAAH! Sideshow Bob!"
* TheChewToy: 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.
* ClassicallyTrainedExtra: ''Much'' to his dismay.
* DeathTrap: 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 [[spoiler: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]].
* DickDastardlyStopsToCheat: In "Sideshow Bob Roberts", Bob steals an election in which Quimby was already a sure loser.
* DubNameChange:
** 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.
* EnemyMine: 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.
* EnmityWithAnObject: Rakes, ever since the OverlyLongGag 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.
* EvenEvilHasLovedOnes: 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.
* EvenEvilHasStandards: 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.
* EvilerThanThou: His brother Cecil[[spoiler:, until "Funeral For a Fiend", when [[MoralEventHorizon he tries to burn Bart alive after successfully convincing everyone to hate him]] ]].
* EvilRedhead
* FailureIsTheOnlyOption: His plans to kill Bart.
* {{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 HeelFaceTurn (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.
* FrameUp: He attempted to frame Krusty by dressing in a Krusty costume and arm rob the Kwik-E-Mart in ''Krusty Gets Busted''.
* HappilyMarried ---> UnholyMatrimony: 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.
* HatesTheJobLovesTheLimelight: This trope is what led to Bob's StartOfDarkness. 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.
* HeelFaceRevolvingDoor: 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'' ... [[MoodWhiplash Joking, joking!]]
* HereditaryHairstyle: He inherited his hair from his mother, which he then passed on to his son.
* HypocrisyNod: 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."
* IneffectualSympatheticVillain: Sideshow Bob frequently veers into this territory; indeed, despite his fame, he had never killed anyone. The poor guy can't even win against a rake.
* InsaneTrollLogic: One of the Bob for Mayor ads in "Sideshow Bob Roberts" accuses Quimby of being soft on crime... for ordering Bob's release.
* IvyLeagueForEveryone: Bob went to Yale.
* KnightOfCerebus: Played with. He's a persistent attempted murderer in a family sitcom, if still a very comedic one.
* {{Leitmotif}}: The [[https://www.youtube.com/watch?v=QH3RhbVP7cA theme from ''Cape Fear'']].
* ManipulativeBastard: 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.
* MonsterClown: Well, ''ex''-clown.
* MotiveDecay: 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. Meanwhile, Bob and Bart seemingly made up during that period. If anything, he should want revenge on Cecil.
* MundaneUtility: 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.
* PetTheDog: Have some. When Krusty's father dies, he came to comfort him. He also saves Bart from his brother once, and refused to team up with Lassen when this latter proposed to kill Bart together.
* PhraseCatcher: "''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!''"
* ReformedButRejected: 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 HappilyMarried 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!
* SelectiveEnforcement: He ultimately only desires revenge against Bart, no matter how much others have crossed him. He interestingly holds nothing against the rest of the Simpson family despite a increasingly similar amount of suffering they have caused. This is especially noticeable for Lisa, who's ruined his plans ''more'' times than Bart now. Although now it's dropped as he declared vendetta on the whole family after the incident in Italy but still want Bart more than the others.
* StatusQuoIsGod: 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 Bob's life from Cecil. He'll always end up back in jail by the end of each episode, no matter what deception he has used to get himself out. Wiggum at one point sent him back in with no evidence, seemingly just to enforce this trope.
* TooDumbToLive: In one episode, while on a houseboat, he honors Bart's last request to sing the entire score to the ''Theatre/HMSPinafore''. During this time, they pass the cops.
* VileVillainSaccharineShow: Like Mr. Burns, Sideshow Bob is usually portrayed more seriously as other villains on the show, though he does have some comic relief moments.
* VillainDecay: Averted, but lampshaded. Bob is always devious and brilliant, but Bart has foiled his plans so often he isn't as afraid of him as he was 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.
* VillainousFriendship: Has one with Lisa in "The Man Who Grew Too Much".
* TheVoiceless: In his role as Krusty's sidekick, he never spoke and only communicated via slide whistle.
* VoteEarlyVoteOften: How he won the mayoral election in "Sideshow Bob Roberts", of the "Ghost Voter" variety. Of course, it might also qualify under DickDastardlyStopsToCheat.
* WellIntentionedExtremist: 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.
* WickedCultured: 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".
* WouldHurtAChild: [[spoiler:Finally gets the chance to kill Bart ([[DeathMontage a lot]]) in the [[Recap/TheSimpsonsS27E5TreehouseOfHorrorXXVI Treehouse of Horror XXVI]] segment "Wanted: Dead, then Alive", [[ComicBookTime after "24 years of trying to kill a ten-year-old child"]]. Well, is a not-canon episode.]]
* YouMeddlingKids: 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..
* YouWillBeSpared: Has outright stated he is only interested in killing Bart. Has lampshaded his apathy towards Lisa on several occasions, even when she is the one who stops him. Bart will ''always'' be his ArchEnemy. Although after they ruined his life in Italy he declares vendetta on the whole family but future episodes shows that he still want Bart dead first and the family has acceptable targets.
[[/folder]]
[[folder: Marion Anthony "Fat Tony" D'Amico]]
[[quoteright:190:http://static.tvtropes.org/pmwiki/pub/images/190px-FatTony_2308.png]]
-->Debut: ''"Bart the Murderer"''
Head of the Springfield Mafia. Voiced by Joe Mantegna.
* AffablyEvil: Depending on the episode really.
* AscendedExtra: Another one of those characters that WordOfGod expected to appear only once, but kept coming back.
* BadassInCharge: He, Legs, and Louie once took on a Yakuza group, and held their own, despite being underarmed and undermanned.
* CharacterizationMarchesOn: He had a thick Bronx accent in his first appearance.
* ExactWords:
** Fat Tony loves invoking these tropes: One instance is 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", [[BestialityIsDepraved 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."
* KilledOffForReal: But [[spoiler: [[TheyKilledKennyAgain replaced by his cousin]]]].
* LegitimateBusinessmensSocialClub: TropeNamer.
* TheMafia
* MySiblingWillLiveThroughMe: Because StatusQuoIsGod, [[spoiler: when he is killed off his cousin replaces him, soon becoming an exact copy of him.]]
* OddFriendship: Homer and Marge actually get on with Fat Tony quite well, despite knowing he's head of the Springfield Mafia.
* {{Retcon}}: His real name. It has at various instances been given as William Williams[[labelnote:*]]Although this was strongly implied to be an obviously fake alias[[/labelnote]], Anthony D'Amico, and [[Creator/JohnWayne Marion]].
* WickedCultured: He was shown to be a quite talented violinist.
[[/folder]]
[[folder: Chester Turley (Snake Jailbird)]]
[[quoteright:200:http://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 Creator/HankAzaria.
* AdventurerArchaeologist: He was formerly an idealistic Indiana Jones-type archaeologist, but became a thief.
* AffablyEvil: In more recent seasons.
* AntiVillain: Again, in more recent seasons. "Goodbye, student loan payments!"
* BerserkButton: Snake hates singing.
* CardCarryingVillain: In earlier seasons. For example, this quote from Season 4:
-->'''Snake:''' (''on breaking out of jail'') All right! Time for a crime spree!
* CatchPhrase:
** "Bye!" and "All ''RIGHT''!"
** "Dude!"
* DespairEventHorizon: In "The Seemingly Never-Ending Story", it's revealed that his crimes against shopkeepers stem from an incident in which a certain barkeeper [[note]] Moe Szyslak [[/note]] took Maya coins from him as he was handing them over to the museum.
* DisproportionateRetribution: 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!
* EvenEvilHasLovedOnes: Has a GenerationXerox [[OverlordJr son]], and a long-term girlfriend.
* GoKartingWithBowser: He is often seen doing things with the police like joining their bowling team and appearing in their calendar.
* GoodParents: Although Snake seems to have committed every crime possible, he is an extremely good father to his son.
* KarmaHoudini: Snake is constantly seen getting arrested, but never appearing to stay in prison for long time.
* LikeAnOldMarriedCouple: With Apu, they once attended couples counseling.
* OlderThanTheyLook: Based on flashbacks, he's probably already close to 40, but he still appears to be around his mid to late 20s.
* PermaStubble
* PetTheDog: He was implied to have a soft spot for puppies and other animals, as, 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.
* SurferDude: He speaks with a "Valley Boy" accent.
* StealTheSurroundings: He robs the Quik-E-Mart. Literally. He loads it onto a truck and drives it away.
-->'''Snake:''' All right! I'm taking this thing to Mexico!
* TattooedCrook: His nickname comes from the prominent tattoo of a snake on his arm.
* UnholyMatrimony: 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 [[AllGirlsWantBadBoys bad boy]] like Snake.
* VillainsOutShopping
* WhatTheHellIsThatAccent: It sounds like a bizarre cross between upper-class British English, Cockney, Australian and Californian.
[[/folder]]
[[folder: Legs and Louie]]
-->Debut: ''"Bart the Murderer"''
Fat Tony's associates. Voiced by Creator/HankAzaria (by Karl Wiedergott in "Trilogy of Error" and "Chief of Hearts") and Creator/DanCastellaneta.
* BackAlleyDoctor: 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.
* {{Mooks}}: Of Fat Tony.
* ThoseTwoBadGuys: Never seen apart usually
[[/folder]]
[[folder: Johnny Tightlips]]
-->Debut: ''"Bart the Murderer"''
Voiced by Creator/HankAzaria.
* AscendedExtra: 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.
* {{Foil}}: To Frankie the Squealer.
* MeaningfulName: 'Tightlips' apt name for a guy who says very little.
* TheStoic: 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:''' [[MathematiciansAnswer I see a lot of things]]!
-->'''Fat Tony''': You know, you could be more a little helpful!
* TerseTalker
[[/folder]]
[[folder: Frankie the Squealer]]
-->Debut: ''"Insane Clown Poppy"''
* ExactlyWhatItSaysOnTheTin: He's a mobster who 'squeals' on his own mafia which leads to....
* {{Foil}}: To Johnny Tightlips naturally.
* TheFriendNoOneLikes: The rest of the mafia clearly don't like him but he never goes anywhere.
* IronButtMonkey: One Halloween episode had the mafia shoot him to no effect while he calls his wife and tells her he'll be home late.
* MeaningfulName: Apt name for the guy really.
* TheMillstone: 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).
* TheStoolPigeon: He compulsively squeals about everything, because it makes him feel big. He even squeals while he's getting beaten up for squealing.
[[/folder]]
----
[[folder:Mayor Joe Quimby]]
[[quoteright:264:http://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 Creator/DanCastellaneta.
* UsefulNotes/AmericanAccents: Joe Quimby and his family speak in a broad UsefulNotes/{{Boston}} (Kennedy-esque) accent, humorously picked up on by Creator/JonStewart whenever he's discussing the Kennedys.
* CatchPhrase: "Vote Quimby!"
* EveryoneHasStandards:
** Despite his ways, he does have his limits like having a woman thrown in jail for her nervous breakdown [[note]] In [[Recap/TheSimpsonsS3E15HomerAlone Homer Alone]][[/note]], and holding the town hostage for monetary reasons [[note]][[Recap/TheSimpsonsWhoShotMrBurns Who Shot Mr. Burns?]][[/note]].
** Though a huge womanizer, he was horrified at the idea of sleeping with his niece.
* FatIdiot: Though nowhere near as bad as Homer or Chief Wiggum.
* FutureLoser: Has lost his lofty political position and become a taxi driver in the hypothetical future episode "Lisa's Wedding."
* ITakeOffenseToThatLastOne: 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.
* KavorkaMan: He is the mayor what he looks like doesn't matter much
* MayorPain: {{Trope Namer|s}} for Type B. An outright corrupt, opportunistic, embarrassing, sleazy politician who couldn't care less for Springfield.
* NobleDemon: 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.
* NoCelebritiesWereHarmed: 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]]Sideshow Bob's campaign commercial scorning Quimby as soft on crime mimics the notorious Willie Horton ad deployed by Dukakis' 1988 opponent for U.S. President, UsefulNotes/GeorgeHWBush[[/note]]. Mrs. Quimby dresses like Jacqueline Kennedy.
* OverlyLongName: Joseph Fitzgerald O'Malley Fitzpatrick O'Donnell the Edge "Diamond Joe" Quimby
* PetTheDog: He was willing to sacrifice television if it meant stopping Sideshow Bob from detonating a nuke.
* ReallyGetsAround: Some are escorts other are mistresses.
* SleazyPolitician:
** In fact, he provides the image page 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 [[BlatantLies 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 [[CorruptPolitician 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.
* ScrewTheRulesIHaveConnections: When Marge suffered a nervous breakdown and blocks traffic on a bridge, she was arrested. Mayor Quimby immediately pulled some strings to get her released without charges, claiming that if she went to jail, he could kiss the "chick vote" goodbye.
* ScrewTheRulesIHaveMoney: When his nephew Freddy was WronglyAccused 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 HairTriggerTemper.
* TheStoner: Smokes pot, and even grows several plants in his office.
* StrawmanPolitical: As the series' most prominent recurring Democratic politician, he serves as the primary target for {{Take That}}s aimed at Democrats and liberals.
* VerbalTic: 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, Bart uses this verbal tic to trick Quimby into thinking he's his son.
* YourCheatingHeart: 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 [[Film/CitizenKane Charles Foster Kane did for his mistress, whose singing voice was good, but not good enough for opera]]).
[[/folder]]
!Judges and Lawyers
[[folder: Judge Roy Snyder]]
[[quoteright:211:http://static.tvtropes.org/pmwiki/pub/images/roy_snyder_official_image.png]]
-->Debut: ''"Krusty Gets Busted"''
Voiced by Creator/HarryShearer.
* AmbiguouslyBrown: His skin color has changed from yellow to brown repeatedly throughout the series to stay brown.
* BunnyEarsLawyer: A good judge for the most part, but has a strange preoccupation with a clown desk figurine.
* FirstNameBasis: 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.
* ReasonableAuthorityFigure: One of the few people with authority in Springfield who is (usually) characterised as competent, non-brutal, and non-corrupt.
* YourCheatingHeart: He admitted in court that his wife had left him, since then he has been seen with Lindsey Naegle.
[[/folder]]
[[folder: Judge Constance Harm]]
[[quoteright:320:http://static.tvtropes.org/pmwiki/pub/images/2054878_judge_constance_harm.png]]
-->Debut: ''"The Parent Rap"''
Voiced by Jane Kaczmarek
* CoolPet: Has a pet seal named Poncho that doubles as a guard dog, and ''barks'' like one.
* DisproportionateRetribution: A lot, such an 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.
* HangingJudge: To give one example of how harsh she can be, in one episode she retracted Homer's driving license for driving it 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 [[Series/MalcolmInTheMiddle Jane Kaczmarek]]. She enjoys creating cruel and unusual punishments for criminals in her court.
** JerkassHasAPoint: That being said she does rightfully call out Homer for being a bad father.
* PetTheDog: In the 300th episode she does grants Bart emancipation from his family, specifically ''Homer'', after his jerkass tendencies reaches new heights.
* MeaningfulName / NamesToRunAwayFromReallyFast: Harm's name is a pun on the phrase "Constant Harm," implying that she likes issuing cruel punishments to people in her courtroom.
* ReasonableAuthorityFigure: Subverted. While she has the appearance of a stern, no nonsense judge, she holds serious grudges against other people.
* {{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."
[[/folder]]
[[folder: Lionel Hutz]]
[[quoteright:250:http://static.tvtropes.org/pmwiki/pub/images/lionel_hutz917.png]]
-->Debut: ''"Bart Gets Hit by a Car"''
-->Final Episode: ''"Realty Bites"''
Voiced by: Creator/PhilHartman
* TheAlcoholic: As implied in "Marge in Chains." He even argued his case before the court and was then informed he wasn't wearing any pants. He's also seen drinking scotch at nine-thirty in the morning. In front of clients, no less.
* AmbulanceChaser: In "Bart Gets Hit By a Car," Homer says upon meeting him, "You were the guy chasing Bart's ambulance."
* BunnyEarsLawyer: Averted. He's eccentric, odd and sleazy. And really, really bad at his job. The rare times he does win a case, it's because of something Bart and/or Lisa did.
* ChuckCunninghamSyndrome: 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.
* FrivolousLawsuit: His usual thing. Heck, he once sued the makers of ''Film/TheNeverEndingStory'' for false advertising.
* MakeTheDogTestify: Does this occasionally.
* SmartBall: 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 will 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.
* UltimateJobSecurity: Frequently lost his cases, but kept getting hired by Homer and Marge regardless. Lampshaded:
-->'''Marge:''' You know, we should really stop hiring him.
[[/folder]]
[[folder: Blue-Haired Lawyer]]
-->Debut: ''"Bart Gets Hit by a Car"''
Voiced by Creator/DanCastellaneta.
* AmoralAttorney: Although unlike most examples, he isn't outright malevolent.
* ArtisticLicenseLaw: A RunningGag is that he'll claim copyright infringement over things that are in the public domain, like Christmas carols. One halloween episodes has him making a solid legal document that would allow Burns to hunt people.
* NoCelebritiesWereHarmed: WordOfGod says he's based on the appearance of actor Charles Lane and the voice and mannerisms of Roy Cohn.
* NoNameGiven: His actual name has never been revealed.
* TooDumbToLive: In the Halloween episode above he is shot right after giving the document that makes it legal for Burns to kill him.
* YouGottaHaveBlueHair: Has blue hair.
[[/folder]]
!Police
[[folder:Chief Clancy Wiggum]]
[[quoteright:180:http://static.tvtropes.org/pmwiki/pub/images/chiefwiggum_3943.jpg]]
->"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 Creator/HankAzaria.
* ArtisticLicenseGunSafety: 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.
* BadCopIncompetentCop: By himself, if he gets lucky or motivated enough to catch you he can be bribed anyway.
* BaitAndSwitch: 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.
* BrilliantButLazy: The episode "Pranksta Rap" reveals that if he's motivated enough, he can make some great police work.
* CatchPhrase: Played with in "[[Recap/TheSimpsonsS11E22BehindTheLaughter Behind the Laughter]]", in which he claims to have one.
-->'''Wiggum:''' N'yeah! Wah! Wah-wah-wah! No, I lost it.
* DirtyCop: He accepts (and often expects) bribes.
* DotingParent: 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.
* FatBastard: Apathetic, self-interested, and more than willing to abuse his authority for his own gain. [[PetTheDog He does love his son though]].
* FatIdiot: He is one of the fattest character and one of the dumbest.
* FatSlob: Big eater and out of shape.
* {{Flanderization}}: Was not such as incompetent in the first season. Wasn't really present either.
* GenreSavvy: Is the TropeNamer 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 days before he retires. … Which is actually a RunningGag regarding the Springfield Police Department's equipment.
* HiddenDepths: 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.
* InspectorJavert: Sometimes.
* InspectorLestrade: When Bart and/or Lisa play AmateurSleuth.
* IOweYouMyLife: 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.
* JugglingLoadedGuns: Has a frequent tendancy to do this.
-->''(on Homer)'' "Well, if it isn't that stupid cop from TV." ''([[HypocriticalHumor proceeds to scratch his ear with the barrel of his gun]])'' "Oh yeah, that got it."
* TheNicknamer: It seems like the only part of his job he's passionate about is coming up with cleaver names for the people he arrests.
* NobodysThatDumb: He tends to have these types of moments.
** In season 23 [[Recap/TheSimpsonsS23E14AtLongLastLeave "At Long Last Leave"]], after the Simpsons were banished from Springfield, Homer and Marge sneak back into Springfield under the disguise of Mr. Burns and Smithers. When Chief Wiggums first spots them, it appears that he fell 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.
* PoliceAreUseless: He has a ''few'' competent moments, but these are far and between. When Homer briefly replaces him as Police Chief and decides to quit, Homer takes off his badge and says he'll offer it to the next person he sees, which turns out to be Wiggum. He's amused because this was actually how he ''first'' got the job.
* SuspectIsHatless: He provides the {{Trope Namer|s}} in "Homer's Triple Bypass".
* StripperCopConfusion: Went along with it for the money.
* SympatheticInspectorAntagonist: Sometimes, when played sympathetically.
* YouGottaHaveBlueHair: Earlier in the show, he had black hair. Became blue as the show evolved in later seasons.
[[/folder]]
[[folder:Sergeants Eddie and Lou]]
[[quoteright:350:http://static.tvtropes.org/pmwiki/pub/images/simpsonsloueddie.jpg]]
--> Debut: ''"There's No Disgrace Like Home"''
Chief Wiggum's second-in-commands. Voiced by Creator/HarryShearer and Creator/HankAzaria.
* AmbiguouslyHuman: Lou was about to vomit after seeing Agnes Skinner and Comic Book Guy in bed together but Eddie says "It's okay, man. If it doesn't affect you, you're not human." .
* CatchPhrase: Lou says, "Uh, Chief?"
* NoCelebritiesWereHarmed: Hank Azaria based Lou's voice on Creator/SylvesterStallone.
* OnlyOneName:
-->'''Guy:''' Now what are your last names?
-->'''Lou:''' We don't have them. We're like Cher.
* OnlySaneMan: Zigzagged. Lou sometimes appears more competent than Wiggum, but he is also capable of being corrupt.
* TheQuietOne: Eddie is usually quiet, though he used to be a bit more chopsier and talked more than he does now.
* RaceLift: Eddie was yellow in earlier episodes but is now black.
* SaltAndPepper: Lou is the Pepper to Wiggum's and Eddie's Salt.
* ThoseTwoGuys: Though Eddie hardly ever speaks and it's Lou that gets the bulk of the characterization.
[[/folder]]
!Criminals
[[folder: Robert Underdunk Terwilliger, Ph.D. (Sideshow Bob)]]
[[quoteright:160:http://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 Creator/KelseyGrammer.
* AffablyEvil: He's usually rather polite and comedic...though he's a psychopath nonetheless.
* AnimeHair: He could be mistaken for a palm tree with the right dye.
* ArchEnemy: Bart Simpson and Krusty the Clown. And [[ArsonMurderAndJaywalking rakes]].
* ArtifactTitle: 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 said "Vote for Sideshow Bob" as opposed to "Vote for Terwilliger" or simply "Vote for Bob". The only time he ever seemed to get angry at the name was when he was 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 [[BerserkButton just made Bob scream in fury while he increases the speed of the plane]].
* AscendedExtra / EarlyBirdCameo: Bob first appears as a silent background character in "The Telltale Head".
* AxCrazy: He started to qualify for this when his attempts to kill Bart included trying to have him cremated alive and when he visibly removed his cell mate's face and cut off his own. He also ties up Bart while singing casually about wanting to gouge out Bart's eyes. And then there's the Treehouse of Horror XXVI segment "Wanted: Dead, Then Alive" which has several moments that are genuinely disturbing.
* BigBadEnsemble: 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.
* BiTheWay: He off-handedly mentions experimenting during college when Homer is surprised that he has a wife.
* CardCarryingVillain: He's an EvilGenius and he's ''not'' particularly modest about the fact, either.
* CatchPhrase: "Hello, Bart".
** PhraseCatcher: "AAAAAH! Sideshow Bob!"
* TheChewToy: 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.
* ClassicallyTrainedExtra: ''Much'' to his dismay.
* DeathTrap: 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 [[spoiler: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]].
* DickDastardlyStopsToCheat: In "Sideshow Bob Roberts", Bob steals an election in which Quimby was already a sure loser.
* DubNameChange:
** 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.
* EnemyMine: 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.
* EnmityWithAnObject: Rakes, ever since the OverlyLongGag 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.
* EvenEvilHasLovedOnes: 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.
* EvenEvilHasStandards: 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.
* EvilerThanThou: His brother Cecil[[spoiler:, until "Funeral For a Fiend", when [[MoralEventHorizon he tries to burn Bart alive after successfully convincing everyone to hate him]] ]].
* EvilRedhead
* FailureIsTheOnlyOption: His plans to kill Bart.
* {{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 HeelFaceTurn (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.
* FrameUp: He attempted to frame Krusty by dressing in a Krusty costume and arm rob the Kwik-E-Mart in ''Krusty Gets Busted''.
* HappilyMarried ---> UnholyMatrimony: 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.
* HatesTheJobLovesTheLimelight: This trope is what led to Bob's StartOfDarkness. 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.
* HeelFaceRevolvingDoor: 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'' ... [[MoodWhiplash Joking, joking!]]
* HereditaryHairstyle: He inherited his hair from his mother, which he then passed on to his son.
* HypocrisyNod: 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."
* IneffectualSympatheticVillain: Sideshow Bob frequently veers into this territory; indeed, despite his fame, he had never killed anyone. The poor guy can't even win against a rake.
* InsaneTrollLogic: One of the Bob for Mayor ads in "Sideshow Bob Roberts" accuses Quimby of being soft on crime... for ordering Bob's release.
* IvyLeagueForEveryone: Bob went to Yale.
* KnightOfCerebus: Played with. He's a persistent attempted murderer in a family sitcom, if still a very comedic one.
* {{Leitmotif}}: The [[https://www.youtube.com/watch?v=QH3RhbVP7cA theme from ''Cape Fear'']].
* ManipulativeBastard: 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.
* MonsterClown: Well, ''ex''-clown.
* MotiveDecay: 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. Meanwhile, Bob and Bart seemingly made up during that period. If anything, he should want revenge on Cecil.
* MundaneUtility: 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.
* PetTheDog: Have some. When Krusty's father dies, he came to comfort him. He also saves Bart from his brother once, and refused to team up with Lassen when this latter proposed to kill Bart together.
* PhraseCatcher: "''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!''"
* ReformedButRejected: 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 HappilyMarried 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!
* SelectiveEnforcement: He ultimately only desires revenge against Bart, no matter how much others have crossed him. He interestingly holds nothing against the rest of the Simpson family despite a increasingly similar amount of suffering they have caused. This is especially noticeable for Lisa, who's ruined his plans ''more'' times than Bart now. Although now it's dropped as he declared vendetta on the whole family after the incident in Italy but still want Bart more than the others.
* StatusQuoIsGod: 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 Bob's life from Cecil. He'll always end up back in jail by the end of each episode, no matter what deception he has used to get himself out. Wiggum at one point sent him back in with no evidence, seemingly just to enforce this trope.
* TooDumbToLive: In one episode, while on a houseboat, he honors Bart's last request to sing the entire score to the ''Theatre/HMSPinafore''. During this time, they pass the cops.
* VileVillainSaccharineShow: Like Mr. Burns, Sideshow Bob is usually portrayed more seriously as other villains on the show, though he does have some comic relief moments.
* VillainDecay: Averted, but lampshaded. Bob is always devious and brilliant, but Bart has foiled his plans so often he isn't as afraid of him as he was 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.
* VillainousFriendship: Has one with Lisa in "The Man Who Grew Too Much".
* TheVoiceless: In his role as Krusty's sidekick, he never spoke and only communicated via slide whistle.
* VoteEarlyVoteOften: How he won the mayoral election in "Sideshow Bob Roberts", of the "Ghost Voter" variety. Of course, it might also qualify under DickDastardlyStopsToCheat.
* WellIntentionedExtremist: 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.
* WickedCultured: 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".
* WouldHurtAChild: [[spoiler:Finally gets the chance to kill Bart ([[DeathMontage a lot]]) in the [[Recap/TheSimpsonsS27E5TreehouseOfHorrorXXVI Treehouse of Horror XXVI]] segment "Wanted: Dead, then Alive", [[ComicBookTime after "24 years of trying to kill a ten-year-old child"]]. Well, is a not-canon episode.]]
* YouMeddlingKids: 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..
* YouWillBeSpared: Has outright stated he is only interested in killing Bart. Has lampshaded his apathy towards Lisa on several occasions, even when she is the one who stops him. Bart will ''always'' be his ArchEnemy. Although after they ruined his life in Italy he declares vendetta on the whole family but future episodes shows that he still want Bart dead first and the family has acceptable targets.
[[/folder]]
[[folder: Marion Anthony "Fat Tony" D'Amico]]
[[quoteright:190:http://static.tvtropes.org/pmwiki/pub/images/190px-FatTony_2308.png]]
-->Debut: ''"Bart the Murderer"''
Head of the Springfield Mafia. Voiced by Joe Mantegna.
* AffablyEvil: Depending on the episode really.
* AscendedExtra: Another one of those characters that WordOfGod expected to appear only once, but kept coming back.
* BadassInCharge: He, Legs, and Louie once took on a Yakuza group, and held their own, despite being underarmed and undermanned.
* CharacterizationMarchesOn: He had a thick Bronx accent in his first appearance.
* ExactWords:
** Fat Tony loves invoking these tropes: One instance is 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", [[BestialityIsDepraved 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."
* KilledOffForReal: But [[spoiler: [[TheyKilledKennyAgain replaced by his cousin]]]].
* LegitimateBusinessmensSocialClub: TropeNamer.
* TheMafia
* MySiblingWillLiveThroughMe: Because StatusQuoIsGod, [[spoiler: when he is killed off his cousin replaces him, soon becoming an exact copy of him.]]
* OddFriendship: Homer and Marge actually get on with Fat Tony quite well, despite knowing he's head of the Springfield Mafia.
* {{Retcon}}: His real name. It has at various instances been given as William Williams[[labelnote:*]]Although this was strongly implied to be an obviously fake alias[[/labelnote]], Anthony D'Amico, and [[Creator/JohnWayne Marion]].
* WickedCultured: He was shown to be a quite talented violinist.
[[/folder]]
[[folder: Chester Turley (Snake Jailbird)]]
[[quoteright:200:http://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 Creator/HankAzaria.
* AdventurerArchaeologist: He was formerly an idealistic Indiana Jones-type archaeologist, but became a thief.
* AffablyEvil: In more recent seasons.
* AntiVillain: Again, in more recent seasons. "Goodbye, student loan payments!"
* BerserkButton: Snake hates singing.
* CardCarryingVillain: In earlier seasons. For example, this quote from Season 4:
-->'''Snake:''' (''on breaking out of jail'') All right! Time for a crime spree!
* CatchPhrase:
** "Bye!" and "All ''RIGHT''!"
** "Dude!"
* DespairEventHorizon: In "The Seemingly Never-Ending Story", it's revealed that his crimes against shopkeepers stem from an incident in which a certain barkeeper [[note]] Moe Szyslak [[/note]] took Maya coins from him as he was handing them over to the museum.
* DisproportionateRetribution: 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!
* EvenEvilHasLovedOnes: Has a GenerationXerox [[OverlordJr son]], and a long-term girlfriend.
* GoKartingWithBowser: He is often seen doing things with the police like joining their bowling team and appearing in their calendar.
* GoodParents: Although Snake seems to have committed every crime possible, he is an extremely good father to his son.
* KarmaHoudini: Snake is constantly seen getting arrested, but never appearing to stay in prison for long time.
* LikeAnOldMarriedCouple: With Apu, they once attended couples counseling.
* OlderThanTheyLook: Based on flashbacks, he's probably already close to 40, but he still appears to be around his mid to late 20s.
* PermaStubble
* PetTheDog: He was implied to have a soft spot for puppies and other animals, as, 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.
* SurferDude: He speaks with a "Valley Boy" accent.
* StealTheSurroundings: He robs the Quik-E-Mart. Literally. He loads it onto a truck and drives it away.
-->'''Snake:''' All right! I'm taking this thing to Mexico!
* TattooedCrook: His nickname comes from the prominent tattoo of a snake on his arm.
* UnholyMatrimony: 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 [[AllGirlsWantBadBoys bad boy]] like Snake.
* VillainsOutShopping
* WhatTheHellIsThatAccent: It sounds like a bizarre cross between upper-class British English, Cockney, Australian and Californian.
[[/folder]]
[[folder: Legs and Louie]]
-->Debut: ''"Bart the Murderer"''
Fat Tony's associates. Voiced by Creator/HankAzaria (by Karl Wiedergott in "Trilogy of Error" and "Chief of Hearts") and Creator/DanCastellaneta.
* BackAlleyDoctor: 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.
* {{Mooks}}: Of Fat Tony.
* ThoseTwoBadGuys: Never seen apart usually
[[/folder]]
[[folder: Johnny Tightlips]]
-->Debut: ''"Bart the Murderer"''
Voiced by Creator/HankAzaria.
* AscendedExtra: 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.
* {{Foil}}: To Frankie the Squealer.
* MeaningfulName: 'Tightlips' apt name for a guy who says very little.
* TheStoic: 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:''' [[MathematiciansAnswer I see a lot of things]]!
-->'''Fat Tony''': You know, you could be more a little helpful!
* TerseTalker
[[/folder]]
[[folder: Frankie the Squealer]]
-->Debut: ''"Insane Clown Poppy"''
* ExactlyWhatItSaysOnTheTin: He's a mobster who 'squeals' on his own mafia which leads to....
* {{Foil}}: To Johnny Tightlips naturally.
* TheFriendNoOneLikes: The rest of the mafia clearly don't like him but he never goes anywhere.
* IronButtMonkey: One Halloween episode had the mafia shoot him to no effect while he calls his wife and tells her he'll be home late.
* MeaningfulName: Apt name for the guy really.
* TheMillstone: 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).
* TheStoolPigeon: 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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