A character sheet for Aaron [=McGruder=]'s newspaper comic strip (turned animated television series) ''TheBoondocks''.

[[folder:Main Characters]]
!!Huey Freeman
->''"Vision? What do you know about my vision? My vision would turn your world upside down, tear asunder your illusions, and send the sanctuary of your own ignorance crashing down around you."''
-->'''Voiced by:''' Regina King

A young black boy who [[FishOutOfWater moves]] with his brother and grandfather from [[TheCity inner-city]] UsefulNotes/{{Chicago}}, Illinois to [[{{Suburbia}} suburban]] Woodcrest, Maryland. [[ChildProdigy Intelligent]] yet [[ThePessimist pessimistic]] for his age, he is a [[SoapboxSadie radical left-wing activist]] and an alleged "domestic terrorist".
* ActingYourIntellectualAge: Huey is very intelligent and mature for a 10 year-old child. He has demonstrated a depth of understanding topics that would seem to surpass his young age such as: politics, religion, the media, businesses and corporations, African-American culture, and American society as a whole.
* AdorablyPrecociousChild: In the pilot episode, Huey is annoyed that the rich white guests at Wuncler's party find his political rants to be cute instead of offensive.
* AfroAsskicker
* AllIssuesArePoliticalIssues / EverythingIsRacist: Especially in the newspaper comics. Huey won't stop talking about politics, controversies, and other stressful thoughts, even at the most awkward of times. He wants to attach political or philosophical meanings to just about everything. He won't even give himself a break on holidays and vacations.
* [[AngryBlackMan Angry Black Boy]]: Especially in the comic, though [=McGruder=] [[http://24.media.tumblr.com/21e72b1a3eaaa92b1885d85ebcd0fad1/tumblr_mgewrfkXKh1rgam01o1_1280.gif has been known to use him to criticize the concept]].
* AntiHero
* AsideGlance: He has done this multiple times (especially in the first season) to get his cynicism or disapproval across.
* {{Badass}}: He's a skilled martial artist.
** AdaptationalBadass: In the comics, Huey's martial arts skills are an InformedAbility. In the cartoon, not so much.
** BadassAdorable: He can kick ass despite being a prepubescent child.
** BadassBookworm: He's very well read and has an interest in politics.
** RetiredBadass: As early as Season 3, he claimed to be retired from revolutionary activism (or "domestic terrorism" depending on one's views).
* BerserkButton:
** In the comics, Republican politicians and annoying black celebrities bothered him to no end, to the point that they're on his mind '''''nearly 24/7'''''.
** In "The Red Ball", he tells the Chinese kickball team that "I do not like being laughed at", and teaches them the hard way.
* BirdsOfAFeather: Huey became best friends with Caesar because of their common political views.
** Well, it was more because they were the only black kids in Woodcrest (besides Riley) and could relate. While he often agrees with Huey, Caesar is generally much less interested in politics and occasionally gets annoyed that it's all Huey ever seems to talk about.
* BlackAndNerdy: Downplayed (in the TV series). A few times he has quoted ''Star Wars'' characters.
* BlueOni: To Riley's Red.
** Also to Caesar's Red in the comics.
* ButtMonkey: He's often ignored and ridiculed whenever he tries making a point, especially by Riley and Granddad.
* TheCassandra: Riley and Grandad often ignore his advice.
* CavalierCompetitor: Over the kickball game. At least until Ming [[ItsPersonal makes it personal]].
* CharacterizationMarchesOn: In the first season, Huey tends to be considerably angrier and perhaps more of a conspiracy theorist. In the following seasons, his politics are focused more on critical observations and critiques and he functions as a voice of reason amongst his family.
* CharacterCheck: He starts quoting Malcolm X in Season 4, and he is not too far off from his character from the comics in some episodes, such as "Freedomland".
* ChildProdigy: Which annoys his teacher.
* TheComicallySerious / TheStoic: He usually keeps a neutral (yet a bit pessimistic) expression on his face, and only a few times has he shown anything else. But see NotSoStoic.
** PerpetualFrowner: Almost always seen with a frown to emphasize his cynical and pessimistic personality.
*** Interestingly enough, an Adult Swim bumper once featured a fan asking the question, "Does Huey ever smile?" The AS team, apparently stumped, claim to have called up Aaron [=McGruder=] to ask. What was the answer? Apparently, the animators are contractually obligated never to depict Huey smiling or laughing, ever. However, Huey has smiled about 5 times in the animated series. Though Aaron denies them as nothing more than animation errors.
* ComplainingAboutShowsYouDontWatch: InUniverse, he does this when he says that the first ''Film/SoulPlane'' was as funny as a lynching. He justifies it by saying that he's also never seen a lynching, but he knows they're not funny. (Granddad tries to argue that he ''has'' seen a funny lynching, but that's neither here nor there.)
* CompositeCharacter: The cartoon version Huey is a combination of comic Huey's radical views and cynicism with Caesar's OnlySaneMan attitude.
* ConspiracyTheorist: Huey is a left-wing radical after all. He believes that racists, corporations, and governments are all scheming to keep black people and the working classes down.
** In the comics, he often accuses his teacher Mr. Petto of intentionally brainwashing his students on behalf of higher powers. Though really, it seems that Petto is just trying to do his job.
** During one winter break, he formed a convoluted theory that '''''SantaClaus''''' is an agent of the Illuminati or New World Order. Oddly though, [[ArbitrarySkepticism he dismissed Santa as being a childish fairy tale]] until he incorporated him into his paranoid conspiracy fantasies.
** Also in the comics, he totally buys into the [[MillenniumBug [=Y2K=]]] scare to a ridiculous extent, to the point of running drills, asking his grandfather to buy a generator, and (perhaps jokingly) expecting irradiated zombies or space aliens to invade. This results in him [[CrowningMomentOfFunny totally freaking out when Granddad pulls a prank on him by cutting the lights just as the New Year hits]].
** Huey is introduced in the pilot episode by claiming that "Jesus was black, Ronald Reagan is the Devil, and the government's lying about 9/11." Either he really believes all of this, was trying to anger/troll a rich white audience, or probably both.
** Later Huey thinks that a government agent (the White Shadow) is stalking him under surveillance, though of course in the show Huey is in fact known and distrusted by the government.
* CrazyPrepared: Let's just say that when shit goes down, Huey is prepared.
** CrazySurvivalist: In "The Fried Chicken Flu", he hoards a lot of supplies to prepare for a great disaster, such as the fried chicken flu epidemic. [[spoiler:Though it all goes to waste, as the "fried chicken flu" is really an outbreak of salmonella that was exaggerated by the media to be far deadlier than it actually was.]]
* CreepyChild: Even though Huey is a little child, he never smiles or laughs, and he's also a wannabe political militant (and he fully expects to be imprisoned for it some day).
** TroublingUnchildlikeBehaviour: Where do we begin? Huey Freeman has: Planned a prison escape, self-made an electric shock glove, brought nunchaku to a cinema, and created a bomb with the intent to assassinate Ed Wuncler II. (Although in Huey's defense, Ed II is a loan shark who isn't above murdering people.)
* CunningLinguist: In the episode "The Red Ball", he has shown to understand and speak fluent Mandarin Chinese.
* TheCynic / ThePessimist: He's the master of negative thinking. No matter the occasion, he will have unpleasant thoughts about it.
** SillyRabbitCynicismIsForLosers: He's often at the receiving end of this.
** SillyRabbitIdealismIsForKids: He probably believes this.
* DeadpanSnarker: It helps that he does in fact have a deadpan personality, and has a penchant for both sarcasm and bluntness.
* TheDeterminator: This applies to the first season only, as later seasons show him to be much more apathetic.
* DirtyCommunist: The US government and right-wing media consider him to be one.
* DisappearedDad / MissingMom: It's implied that his parents are deceased.
* DisapprovingLook: The boy is famous for it. Just look at his character image. Particularly noticeable in the show, which is less dialogue-heavy and has more moments of Huey just looking at people to get his skepticism or disapproval across, but even in the comic, the {{Beat Panel}}s of Huey just looking at someone who is being ignorant or foolish are common.
* TheEeyore: He sometimes crosses over with GrumpyBear. His endless war against TheMan has left him without the ability to take much enjoyment from things. Naturally, [[http://24.media.tumblr.com/b9bbb13cb590d7055e0050a25aac0f81/tumblr_mm7yvqqUPT1rgam01o1_1280.gif his being a constant downer causes Caesar no shortage of annoyance]], [[http://25.media.tumblr.com/c6863869afa75145aa8eb165b66c4f17/tumblr_mgdj39nCFv1rgam01o1_1280.gif ostracizes him from what friends he has at times]], and every once in a while results in him being called out on it.
* FascinatingEyebrow
* FishOutOfWater: The Freeman family are urban blacks moving into a white suburb, where it seems that there's hardly any other black people around.
* FunnyAfro: There's a running gag in the comic series about Granddad demanding that Huey should get a haircut.
* FreudianTrio: [[TheSpock The Superego]] to Robert's [[TheKirk Ego]] and Riley's [[TheMcCoy Id]].
* GenreSavvy: Listen to the kid. It might just save your life.
* HypocriticalHumor: In the comic. Caesar is usually responsible for calling him on it.
-->'''Huey:''' Most people don't have the time or the energy to follow politics, and the government takes advantage of that. This country needs to keep a closer eye on Washington! We need to start holding our elected officials responsible for this mess!
-->'''Caesar:''' Wow... So who is our Congressman, Huey?
-->'''Huey:''' Who knows... Some punk...
* IgnoredExpert: Yes. He uses his knowledge of the actions and the personalities of the people involved to know roughly of what is going to happen in the future. Not that anyone listens to his warnings.
** For example, in "The Fundraiser", Huey accurately predicts what will become of Riley's candy-selling racket, going so far as to give him a bulletproof vest, which eventually turned out to save his life.
* InsufferableGenius: Particularly in the comic. For example, one year for Christmas, he gave everyone he knew free coupons for hour-long lectures from him on a flaw of theirs of ''his'' choice.
* IntelligenceEqualsIsolation: Huey has very few friends. He scares everyone off except for [[BirdsOfAFeather Caesar]] and Jazmine (especially in the cartoon, due to Caesar's absence).
* IntergenerationalFriendship:
** With Tom, at least as much as Huey's cynicism will allow.
** Also develops this with The White Shadow to an extent.
* IWarnedYou: Writer of "I Told You So: Emergency Household Protocols For Catastrophic Scenario".
* {{Jerkass}}: He's very arrogant and condescending to just about everyone. These traits were especially pronounced in the comics.
** JerkWithAHeartOfGold: But underneath that cynical elitism, he does care about the well-being of his family and friends.
* KatanasAreJustBetter: He plays it straight and also subverts it when he gets in a fight with Riley.
* KnightInSourArmor: Is often bitter and cynical about how little effect his work actually has on the world, and the small chance of him making any sort of difference whatsoever, but still does what he feels needs to be done.
* LackOfEmpathy: In the comics, he can sometimes be a rare heroic example. Though he does care about people, [[http://www.gocomics.com/boondocks/2005/07/31 he often has little tolerance for other peoples' feelings, emotions, and problems]], especially in comparison to what he ''thinks'' [[InsufferableGenius their feelings, emotions, and problems ought to be]].
* MeaningfulName / NamedAfterSomebodyFamous: Named after [[http://en.wikipedia.org/wiki/Huey_P._Newton Huey P. Newton]], co-founder of the Black Panther Party.
** Incidentally, Huey P. Newton was named for Louisiana governor [[http://en.wikipedia.org/wiki/Huey_P._Long Huey P. Long]], making this kind of a layered example of the trope.
* MundaneUtility: In the comics, he often tries to use his skills at revolutionary rhetoric and great berth of knowledge of black history to, among other things, get out of mowing the grass. It always fails.
* NervesOfSteel: He didn't even flinch at the end of the "Attack of the Killer Kung-Fu Wolf Bitch" episode when [[spoiler:Luna killed herself with a grenade]] or when he and Riley pointed the airsoft's at each other's faces. Riley's hand shook and trembled; Huey's was still as stone.
* NeverLiveItDown: InUniverse. For a while in the comics, he's unable to live down the extreme extent to which he bought into Y2K.
* NobleMaleRoguishMale: A relatively noble one.
* NoRespectGuy: To pretty much everyone. Jazmine, however, is an exception as she is the only character, in the whole series, who has consistently shown to listen and even follow Huey.
* NoSenseOfHumor: Beyond his sarcasm, he really doesn't seem to have an interest in comedy. A {{running gag}} in the comic has Caesar either [[http://hueyfreemanonlyspeaksthetruth.tumblr.com/image/61910144892 pointing it out]], [[http://hueyfreemanonlyspeaksthetruth.tumblr.com/image/53708237802 failing to tell him a joke]], or trying and failing to get him to say something funny. One mini-arc even has him trying to teach Huey to tell "[[YourMom your momma]]" jokes, with disastrous results.
* NoSocialSkills: Sometimes, not that he cares. He doesn't really have time for tact, hates most things, and is especially hard on ignorance, which everyone around him has in spades. He doesn't have many friends, but then that doesn't matter to him either. Because of this, characters rarely approach him in a social setting, so this only comes out occasionally. [[http://24.media.tumblr.com/c1315aca790a2698dca52bfcace78ef2/tumblr_mgbteyU4ZT1rgam01o1_1280.gif Poor Jazmine...]]
* NotAllowedToGrowUp: Huey, like all the other children, [[ComicBookTime isn't shown to be aging]]. This is especially confusing in the comics, as he regularly discussed then-current events; this was lampshaded when Caesar commented how the previous US presidential election (four years before that particular strip) felt just like yesterday.
** The show runs for a total of 9 years (including the awkward hiatuses in-between the 4 seasons). Although the only events that could be dated down was the election and inauguration of Barack Obama in 2008-2009.
* NotSoAboveItAll: In the comics, Huey thinks he's an OnlySaneMan, but not really realizing how extreme his viewpoints are, or that in the end he's still just a little kid.
* NotSoStoic: Occasionally you can see Huey look distressed, such as when his former friend Cairo rejects him.
** WhenHeSmiles: Rarely though, you can see Huey in a better mood. And it's actually quite [[http://fc03.deviantart.net/fs22/f/2007/360/5/2/Huey_Freeman__s_smiles_by_MadMassa13.jpg nice]]. Although it has been stated that those instances of him being happy are animation errors, it works for his character as those particular moments of uncharacteristic happiness have something to do with what's happening or who he is speaking to.
*** He smiles when he asks Jazmine to go and assist him on his plan to bust a wrongfully convicted prisoner. Although this was temporary when Jazmine stated that she could not go.
*** He smiles when he set up a soapbox and sees Jazmine across the street with her lemonade stand.
*** He seems genuinely happy to see Granddad return from his Costa Rica trip.
*** He smiles twice when Riley starts having success during the basketball game.
* NWordPrivileges: He says "nigga", but not as much as Riley or Robert do.
* ObliviousToLove: Sometimes. Jazmine occasionally implies that she has some kind of crush on him, to which he's usually as brusque as ever, sometimes even ''more so'' than usual. For instance, at one point in the comic, Jazmine gives him a Valentine. When she asks if he has one for her, he tells her he does and that that he'll be right back with it. He then shuts the door in her face and leaves her waiting outside. [[{{Jerkass}} For two hours, until someone shouts at her to go home]].
* OnlySaneMan: In the TV show, due to the exaggerated stupidity of many characters, especially compared to Riley (not surprisingly), and even his Grandadd (who is much dumber than his comic counterpart).
* OutOfFocus: In the first season, Huey was a lot more outspoken and would actively try to prevent whatever disaster is happening due to the actions of the other characters. In the later seasons, Huey is a lot more apathetic, and his role in many episodes is to offer a few pointed comments and warn the other characters that whatever they're doing is going to blow up in their face, and he mostly lets them deal with the consequences when they don't listen to him.
* ThePiratesWhoDontDoAnything: Huey is a far-left-wing activist who dreams of becoming a militant revolutionary, although he never actually gets to commit any crimes (there was an attempted prison break-out and an attempted assassination of Ed Wuncler II, although both of these plans failed before Huey could even execute them). Nevertheless Huey gets a lot of media and government attention, and he's been branded as a domestic terrorist.
* PoliticallyIncorrectHero: Particularly in the comics, at least at first. Huey is a black nationalist, so he tended to treat white people with some disdain.
** Huey seems to be dismissive about Jazmine's racial identity confusion, [[http://en.wikipedia.org/wiki/One-drop_rule insisting that she's black]] (never mind that she also qualifies as white).
** At one point Huey is convinced that there may be a UsefulNotes/KuKluxKlan presence in Woodcrest, and he even suspects the very liberal and [[WhereDaWhiteWomenAt black-loving]] '''''Sarah [=DuBois=]''''' of being affiliated.
** Although Huey doesn't hate white people as a whole, and also has just as much vitriol for black people, so maybe he's just more of a misanthrope.
* PosterGalleryBedroom: His (half of the) room is neat with a full bookshelf, a computer and posters of Che Guevara and Malcolm X.
* PowerFist: The "Black Power Fist". He builds one with instructions from the Internet.
* PsychicPowers: An odd example, as ''TheBoondocks'' as a series only ever slightly ventures into UrbanFantasy territory in its cartoon iteration, but Huey has a tendency to come across information that he would have otherwise never known about in unnatural ways.
** DreamSpying: When Stinkmeaner [[LikeABadassOutOfHell ascended from hell]], Huey had a dream of it happening that same night. When he told Robert about it, he tried to reassure him that Stinkmeaner was dead and [[AnxietyDreams it was just a dream]]. [[TheCassandra Quite obviously, that wasn't the case]].
*** Similarly, but with much less at stake, in the comic strip Huey had a dream that his Granddad had "betrayed" him by getting a government job. He confronted his granddad about it, asking if he had perhaps gotten work as a mailman. At this point, Robert reveals to the boys that he has just gotten work as a census taker, much to Huey's dismay.
** MySignificanceSenseIsTingling: When Stinkmeaner's spirit is running around spreading discord in Tom's body, they cut to a shot of Huey on his hill, narrating the fact that he could sense an evil force gathering nearby, unable to shake the feeling nor the memory of his earlier dream from his mind.
** SpiritAdvisor: He's the only person who can see or hear the voice of the blue ''Franchise/StarWars'' ghost version of [[Music/WuTangClan Ghostface Killah]], (who isn't ''actually'' dead, so this trope cannot fall into the ISeeDeadPeople category).
*** The White Shadow, who for most of his existence seemed to be a non-supernatural, imagination-based entity, became something of a SpiritAdvisor to Huey in the episode "It's Goin' Down". The key element that made him not just a hallucination that spits out things Huey had heard earlier in the day like he was in the episode "The Real", was that the White Shadow warned him of the imminent invasion of his home by actual federal agents, something that Huey had no idea was going to happen. What or who the White Shadow is remains to be seen.
* TheQuietOne: He's generally very calm and reserved, especially after Season 1.
* RageBreakingPoint: Not prone to overt anger (his rage is usually more [[TranquilFury calm]]), but after Bush gets re-elected he spends two weeks holding it in and then explodes pretty much at random. Caesar has to physically restrain him [[ItMakesSenseInContext from ranting himself off of a cliff.]]
--> '''Huey:''' "It's like middle America called a meeting and said, 'what's the best way to crush Huey's hope for the future?' ... '''MISSION ACCOMPLISHED B***CHES!"'''
--> '''Caesar:''' "Healthy... getting it out is healthy..."
* RaisedByDudes / RaisedByGrandparents: He and Riley are raised by their grandfather Robert.
* RantInducingSlight: He's usually very calm, even in frustration, but when he's in a foul mood watch out. One arc in the comics had him sulking in a particularly drawn out bad mood, and Jazmine tries to cheer him up by giving him a card... which was unfortunately covered in cherubic looking white children. When he sees this, Huey explodes on her so badly that [[JerkWithAHeartOfGold she starts crying and he immediately apologizes]].
-->'''Jazmine''': "I thought it was the thought that counts!"
-->'''Huey''': "YOU WEREN'T THINKING!"
* RedOniBlueOni: Blue to Riley and Caesar's red. Red to Tom's blue.
* [[FoolishSiblingResponsibleSibling Responsible Sibling]]: To Riley's Foolish Sibling.
* RidiculousProcrastinator: Huey gets an entire arc about how he can't get himself to just mow the grass. Even afterward, him doing absolutely anything he can to avoid doing it becomes a RunningGag.
* SeriousBusiness: The nerd in him will quote Obi-Wan Kenobi and he's repeatedly overreacted when he's given news of bad black movies etc. by Caesar.
** He was also determined to write a serious dramatic play for his elementary school, but he fired all the kid actors. [[ComicallyMissingThePoint He didn't understand why the parents were annoyed by this.]]
* SmallNameBigEgo: While Huey isn't so concerned with self-image like Riley is, he does have some traits of this due to being a self-described revolutionary activist, believing he could change the world ([[ThePiratesWhoDontDoAnything despite not doing much besides complaining all the time]]).
* SoapboxSadie: In the episode, "The Block is Hot". However, that is still a natural element to his character.
* TheSpock
* StraightMan
* StrawCharacter: Huey is a far-left radical who preaches socialism and black nationalism. [[DependingOnTheWriter It varies greatly]] whether he's a strawman of a [[NotSoAboveItAll fringe]] [[NotSoDifferent extremist]]...
** StrawmanHasAPoint: Or he's being used as a [[AuthorAvatar mouthpiece]] for [[AuthorTract Aaron [=McGruder=]'s views]].
* SugarAndIcePersonality: Huey is stoic and often blunt, but when the chips are down, so is his personal barrier.
* {{Ubermensch}}: Deconstructed. Initially, he was something of a milder case. But as the series progresses, he has his faith challenged in ways that force him to accept there are forces he can't understand and sometimes he can't make a difference. As the series progresses, Huey starts to become more and more hopeless to the point of eventually giving up on society and accepting that his outlook is not enough.
* TheUnfavorite: Implied in the animated series because he's less likely to go along with his Granddad's crazy schemes than Riley is. On the other hand, do we ever see him getting belt-whipped by Granddad? Though of course Riley causes most of the trouble.
* TheUnreveal: We never get to find out who his parents were.
* UnreliableNarrator: In "Attack Of The Killer Kung Fu Wolf Bitch", though he corrects himself.
* ViolenceReallyIsTheAnswer: He strongly believes this.
* WeekendInventor: He creates an electric shock glove (called the "Black Power Fist"), an emergency power generator (during an outbreak of [[spoiler:salmonella]]), and chemical explosives (he considered killing Ed II).
* WellIntentionedExtremist
* WiseBeyondTheirYears: In the cartoon he certainly acts like this, but the reality is that it's just that: an act. In truth, he just has more common sense than Robert or Riley. He certainly is very mature for his age and he has plenty of knowledge, but he doesn't have all of the intelligence to back it up.
* TheWorfEffect: While a skilled martial artist, he is often the one kissing concrete when he gets into fights, though to be fair, a lot of his opponents are adults and elite {{Badass}}es. The only fights he has won or at least, had the advantage in, were against either those in his own age group, or just {{Mooks}}.
* VitriolicBestBuds: In a one-sided way with Jazmine, who is much nicer to him.
* {{Sibling Yin|Yang}}

!!Riley Freeman
->''"Game recognize game, and you lookin' kinda unfamiliar right now."''
-->'''Voiced by:''' Regina King

Huey's younger brother, a wannabe gangster and juvenile {{delinquent}} with an eye for trouble. He's determined to do anything stupid enough to build up his "reputation".
* AdaptationDyeJob: Not a dye job but a hairstyle change. Riley's hair was changed from being short to having cornrows.
** It should be noted that his hairstyle also changed later in the comic's run; in fact there was an arc about him growing his hair out.
* AesopAmnesia: Has a certain mindset of how the world should work, so any lessons that don't line up with it are immediately discarded.
** Lampshaded at the end of "The Fundraiser". When Riley is offered an opportunity back into the candy business, he recalls all the crap he went through near the end of the episode ([[ItMakesSenseInContext such as narrowly escaping a shootout between two rival gangs and the FBI]]). He then smiles deviously and the credits roll.
* AnnoyingYoungerSibling / BrattyHalfPint
* AscendedFanboy: He's a huge fan of gangsta rappers and is friends with a few of his idols, including Thugnificent and Gangstalicious.
* {{Badass}}
** BadassAdorable: [[DependingOnTheWriter Sometimes]], see the trope below.
** CrouchingMoronHiddenBadass: Despite not having any actual training and just being a kid, Riley has little sense of fear, and will take on ANY opponent, adult or not, that he thinks have wronged him. [[ButtMonkey He usually won't win]], but he puts up a hell of a fight.
** IJustWantToBeBadass
** TookALevelInBadass: He is ''far'' more agile and spry in season four, such as doing impressive aerial flips.
* BookDumb / TheDitz / ObfuscatingStupidity: DependingOnTheWriter; In the comics, he invokes this intentionally. But in the cartoon, he really ''is'' that stupid.
** In the comics, outside of being a talented artist, he is also exceptionally bright when he wants to be. He does poorly in school to protect his "rep".
** He does also learn to be a great artist during an episode in the first season of the show.
** In the first season, Riley was more on the fence when it came to obfuscating stupidity. For all the dumb things he did, the boy was a surprisingly good debater.
** Also, he showed remarkable cunning in "Let's Nab Oprah" by misdirecting Oprah's bodyguards which included Bushido Brown, certainly more cunning than Ed III & Gin Rummy have ''ever'' shown.
** The third season of the cartoon also brings him closer to this; he is, among other things, a master strategist, but is ''willingly'' GenreBlind to an extent that would require him to be secretly GenreSavvy.
* ButtMonkey: In the cartoon. He got his ass handed to him by the local bully, who stole his chain on top of it; Edd III and Gin Rummy stole his pimped out bike he worked really hard on; and Huey absolutely dominated him in the "Home Alone" episode.
* CatchPhrase:
** "Nigga, you gay."
** "Pause."
* CharacterExaggeration: Becomes more of a TedBaxter in the animated series, and even moreso after the first season. Somewhat justified in that Riley is supposed to represent black youth stirred in the wrong direction, imitating rappers. During the time of the strip most rappers were known for how "hard" or "gangster" they were. Currently most rappers are known for how flashy and braggadocios they are.
* CutenessProximity: One of Grandad's crazy ex-girlfriends tried to [[ImTakingHerHomeWithMe kidnap Riley because of how adorable he was]].
* {{Delinquent}} / EnfanteTerrible: Well he is a wannabe gangster after all. He really believes that getting into trouble with the law will make him cool.
** TroublingUnchildlikeBehaviour: Very foul-mouthed and a willing accomplice to some of Ed III's and Rummy's crimes.
* {{Determinator}}: He's not a very good fighter, but good luck on getting him to stay down.
* DisappearedDad / MissingMom: It's implied that his parents are deceased.
* EnemiesEqualsGreatness: He's a firm believer in this trope, but [[WrongGenreSavvy unfortunately]], this led Butch Magnus to steal his chain.
* EvenEvilHasStandards: Though he has an eye for trouble and is extremely callous, he generally draws the line at doing things that directly hurt people. [[DependingOnTheWriter Usually.]] It often depends on his role in the plot - if he's being an antagonist or a VillainProtagonist, then he'll be worse, but if the gag is that he's in over his head he'll always have a line he won't cross. In particular, he is thoroughly creeped out by Lamilton, and is often appalled at how extreme Ed and Rummy can be (not that it stops him from calling them).
* EvilLaugh: His sadistic snicker.
* FishOutOfWater: The Freeman family are urban blacks moving into a white suburb, where it seems that there's hardly any other black people around.
* [[FoolishSiblingResponsibleSibling Foolish Sibling]]
* FreudianTrio: [[TheMcCoy The Id]] to Robert's [[TheKirk Ego]] and Huey's [[TheSpock Superego]]
* FullyAutomaticClipShow: Him calling things gay In "The Story Of Gangstalicious, Part 2".
* GenreSavvy: He can predict the outcome of his Granddad's Catcher Freeman story, which sounds an awful lot like a cliched action/romance movie.
* GirlsHaveCooties
--> ''(After Riley complainins that he might never be able to have money and girls like the rappers on T.V.)''
-->'''Huey:''' Riley, you don't even LIKE girls!
-->'''Riley:''' I DO SO! ''([[{{Beat}} beat]])'' Just as long as they don't touch me...
* GoodOldFisticuffs
* GuiltyPleasures: He feels great shame when it's revealed he's a [[http://en.wikipedia.org/wiki/Lauryn_Hill Lauryn Hill]] fan. This isn't because Hill is a regular guilty pleasure, [[http://www.gocomics.com/boondocks/1999/07/16/ as Huey explains]] - he doesn't see Hill's positive messages as compatible with his chosen "gangsta" lifestyle. He has an image and mindset to maintain.
* HaveIMentionedIAmHeterosexualToday: When he is introduced to something or someone that is or he considers to be gay, he will either criticize, state, or mention that he is straight.
* IntergenerationalFriendship: With Thugnificient.
* {{Jerkass}}: He doesn't care about how his actions affect others (or himself).
** JerkWithAHeartOfGold: [[DependingOnTheWriter Sometimes]].
* KidsAreCruel: He's (usually) not really that bad, but he plays up the "schoolyard tough" act in school in order to build up his "rep." [[http://hueyfreemanonlyspeaksthetruth.tumblr.com/image/41319998572 Though some strips imply that he doesn't really have to try that hard...]]
* LargeHam
* LaserGuidedKarma: While Riley [[AesopAmnesia never learns any lessons]], he doesn't always escape consequences. He usually serves to be his own downfall and often gets beaten by his grandfather if he pisses him off.
* TheMcCoy
* MistakenForGay:
** In the comics, Cindy finds out that Riley likes Lauryn Hill, so then she assumes that he has other effeminate interests.
** In the show, Riley unwittingly copies the behavior of gay rapper Gangstalicious, up to and including wearing Gangstalicious' new clothes (Riley unknowingly looks like he's cross-dressing), so Robert and Ruckus are worried that he's also a homosexual.
* NobleMaleRoguishMale: The roguish one to Huey's noble one.
* NWordPrivileges: Riley says "nigga" very casually. Lampshaded in "The S-Word", when Riley says the word to his white teacher Mr. Petto, who then copies him. Riley and Robert pretended to be offended so they can sue the school district.
* ObnoxiousSnarker: Is a total smart ass, but is generally more obscene than deadpan.
* RaisedByDudes / RaisedByGrandparents: He and his brother are living with their grandfather Robert.
* RedOni: Red to Huey's Blue.
* {{Schemer}}
* ShakingTheRump: Does this in "The S Word" where Huey lampshades he's doing the "Celebratory Booty Dance".
* SmallNameBigEgo: Oh so much, Riley is very obsessed with proving himself to be an awesome gangster.
* ThisLoserIsYou: Riley embraces every negative stereotype about black youth: an anti-intellectual and self-absorbed trouble-maker.
* TokenEvilTeammate: Often.
* TooDumbToLive: At times, such as "The Fundraiser" where he's too cocky and arrogant to realize that dangerous criminals are threatening his life and safety.
* ToxicFriendInfluence: Riley likes to associate with known criminals such as Ed Wuncler III and Gin Rummy, which Huey rightly chastises him for. Riley also starts to hang out with another juvenile delinquent named Lamilton Taeshawn, [[EvenEvilHasStandards but even he scares him]].
** And to a lesser extent, Riley's friendships with gangsta rappers such as Gangstalicious and Thugnificent's Lethal Interjection Crew. While they're all a bunch of dim-witted hedonists, they're also [[JerkWithAHeartOfGold decent guys at heart]].
* TrashTalk: He will insult anyone and will not care for whatever the response is.
* UngratefulBastard
* TheUnreveal: We never get to find out who his parents were.
* UnsympatheticComedyProtagonist
* VerbalTic: He seems to have picked up a new one lately whenever he mentions something gay, no homo.
* VillainProtagonist: He finds a criminal lifestyle to be very appealing. He's already assisted local crooks such as Ed, Rummy, Lamilton, etc.
* TheWorfEffect: Even worse then Huey as he has no muscles, isn't trained and his style is just straight up brawling. At the very least, he has some high stamina and can take a lot of punishment. But that just means he get tossed around like a ragdoll.
* [[SiblingYinYang Sibling Yang]]

!!Robert Jebediah "Granddad" Freeman
->''"Y'all need to start appreciating your Grandaddy! I went and spent your inheritance on this beautiful house in this neighborhood, and all I ask you to do is act like you got some class..."''
-->'''Voiced by:''' John Witherspoon, Aaron [=McGruder=] (young)

The grandfather of Huey and Riley. He was a UsefulNotes/WorldWarII fighter pilot and a UsefulNotes/CivilRightsMovement activist. He wants to live out his last days comfortably, but has to contend with his grandsons' antics, while his own pursuit of money and women get him into trouble.
* [[AbusiveParents Abusive Grandparent]]: Being an old-fashioned parental figure, Robert believes that beatings are a great way to discipline a bad child. He mostly beats up Riley, and rarely Huey.
* AdultsAreUseless / [[BumblingDad Bumbling Granddad]]: As Robert isn't very mature himself, he seems quite incompetent at raising his grandkids. Also see ManChild down below.
* AesopAmnesia: Much like Riley, he has trouble learning from his mistakes. This is lampshaded (or perhaps exaggerated) at the end of the third season:
-->'''Granddad:''' Wow, Huey. [[CassandraTruth You were totally right this time]]. [[CouldHaveAvoidedThisPlot Just imagine all the problems we could avoid if we just listened to you]]. Oh well.
* AngryBlackMan: 'Cause he's a GrumpyOldMan.
* AwesomeMcCoolname: Robert "Bitches" Freeman.
* {{Badass}}
** BadassGrandpa: [[DependingOnTheWriter Sometimes]], see the trope below.
** CrouchingMoronHiddenBadass: Robert has a bit of a cowardly streak, but he can prove to be good at fighting.
** RetiredBadass: He was a Tuskegee Airman during World War II, and also a Civil Rights Movement activist (although he joined reluctantly).
*** AcePilot: He received a medal for flying a "top-secret mission to Germany to save the whole world".
*** BadassPacifist: Averted/defied when he accidentally joined the Freedom Riders, and their leader Sturdy Harris forced him to stay along. Robert considered nonviolent resistance to be suicidal; [[ScrewThisImOuttaHere he preferred to run away from the whole ordeal if he was able to]], [[ViolenceReallyIsTheAnswer although he fights back against an angry mob of white supremacists]].
* BeenThereShapedHistory
** Although how much of it is true [[UnreliableNarrator is uncertain, to say the least]]. He definitely was a Tuskegee Airman and present [[WrongGenreSavvy (albeit deeply unpopular)]] at Rosa Parks' bus protest and the Birmingham marches, definitely ''wasn't'' the UFC light-middleweight champion or a member of G-Unit, and may or may not have gotten into a knife fight with Jesse Jackson.
** Well, actually, the Rosa Parks thing was revealed in an episode that turned out all to be Huey imagining what would happen if Martin Luther King had fallen into a coma and woken up in the year 2000 rather than dying, so that one may not be true, either.
** Turns out he ''was'' a [[http://en.wikipedia.org/wiki/Freedom_Riders Freedom Rider]]... albeit entirely against his will as he got on the wrong bus.
* BerserkButton:
** Asking him to butter his own popcorn.
** He tells Slickback that he can't hurt any women in his presence.
* BlatantLies: "I'm gonna go find myself a white man and lie to 'im right now."
* ButtMonkey: Usually due to whatever stupid mistakes he makes, he often brings down a lot of bad luck upon himself.
* BystanderSyndrome: Prone to this attitude, especially in the comics.
* CasanovaWannabe / DirtyOldMan / KavorkaMan: Despite his old age and fat belly, he never stops chasing after young women. Though something is usually wrong with the women he dates...
** They've included a lazy [[GoldDigger gold-digging]] [[TheOldestProfession prostitute]], [[{{Gonk}} several ugly women]] who pretended to be sexy online, a [[AxCrazy crazy and homicidal]] [[DarkActionGirl martial artist]] who nearly killed him, a [[TheCartel Dominican drug boss]], a crazy woman who [[ImTakingHerHomeWithMe kidnapped Riley]] [[CutenessProximity because of his cuteness]], a [[MorallyAmbiguousDoctorate shady doctor]] who almost [[OrganTheft harvested his organs]], etc. [[ParodySue Ebony Brown]], who seems to be just as perfect as she appears to be, comes as a real surprise; yet Robert still ends up ruining their relationship anyway.
* CatchPhrase:
** "Boy, where's my belt?!"
** Not really a phrase, but Granddad has that little tune he sings constantly with the words being just about anything on his mind at the time.
--->New shoes, New shoo-oo-oo-oo-''ooo''-oes!\\
Good food, Good foo-oo-oo-oo-''ooo''-ood!\\
Soul Plane, Soul Pla-aa-aa-aa-''aaa''-ane!
* ConfirmedBachelor: Of the CasanovaWannabe variety. Even on the rare occasion when he finds himself in a relationship with a woman who seems into him, he shows no desire to marry. In the first episode of the animated series, he tells Ed Wuncler Sr. that he believes "all marriage is wrong", although he may have been joking or avoiding the question of his stance on gay marriage or both.
** Although there is passing mention about his (probably deceased) wife of many years.
* CoolOldGuy: More so in the comics.
* DeadpanSnarker: Granddad often makes dismissive replies to whatever Huey or Riley were going on about.
* DeepSouth: He seems to have lived in this region in his early life. He got himself (in)voluntarily tangled in the political strife there during the height of the Civil Rights Movement.
* DirtyCoward: This is at least implied when he has a nightmare about being chased by an army of Stinkmeaner clones. He abandoned and sacrificed all of his friends and family so he could save his own skin! Who knows if he would do the same in real life?
* EmbarrassingNickname: Thugnifficent refers to him as "Old Nigga".
* FanDisservice: We frequently see him (semi-)naked.
** NakedPeopleAreFunny: At least when they're censored.
* FishOutOfWater: The Freeman family are urban blacks moving into a white suburb, where it seems that there's hardly any other black people around.
* FreudianTrio: [[TheKirk The Ego]] to Huey's [[TheSpock Superego]] and Riley's [[TheMcCoy Id]]
* GrumpyOldMan / ScrewPolitenessImASenior
* HeWhoFightsMonsters: During Robert's conflict with Stinkmeaner's clone, he slowly turns into another copy of Stinkmeaner (figuratively speaking) by embracing the hatred. Huey only manages to turn Robert back to normal, just before he could kill Stinkmeaner again.
* HorribleJudgeOfCharacter: When it comes to choosing women to date.
* HypocriticalHumor: A true master.
** HypocrisyNod: Especially in the comics - a common gag is for Huey to point out how he's acting foolish or hypocritical, only for Granddad to agree, but reply that since he's in his golden years he doesn't care.
* IJustWantToBeNormal: In the comics, where he simply desires to live his golden years in relaxation.
* IJustWantToBeSpecial: In the show, where he's big on appearances and often wants to live the high life.
* ImprobableWeaponUser / WeaponOfChoice: If he needs to fight, it's a good bet that he'll be [[DontMakeMeTakeMyBeltOff using his belt]] as a whip and lasso. He mostly just uses it to punish Riley though.
* IndenturedServitude: [[spoiler:In the fourth season, he signs a contract that forces him to work for Ed Wuncler Jr until he pays off the debt on the house.]]
* IntergenerationalFriendship: With Tom.
* IWasQuiteALooker: As seen during "Wingmen" and "Freedom Ride Or Die", he was a handsome fella in his day.
* {{Jerkass}}: Robert usually places his interests before everyone else, and is quick to avoid responsibility.
** JerkWithAHeartOfGold: Sometimes. He does love his grandsons, no matter how much of a pain in the ass they are.
* LargeHam: He's a master at overreacting to everything, whether it's justified or not.
* ManChild: Especially in the TV series. You know that something's wrong with the Freemans' family dynamic, when prepubescent Huey acts far more adult-like than his old man.
* MeaningfulName: Which Ed Wuncler II [[LampshadeHanging hangs a lantern on]].
* {{Mentor}}: Of a sort to Huey in the comics, where his characterization is that he ''is'' OlderAndWiser, but because he's retired he really doesn't want to have to care. Huey occasionally comes to him for deep conversation, though it's never guaranteed that Granddad will want to get into the situation.
* NoHoldsBarredBeatdown: [[spoiler:He does not even have as much as a welt on him in his final battle with Stinkmeaner.]]
* NWordPrivileges: Lampshaded as far back as the pilot episode, when Robert tells his boys that they shouldn't use the N-word, [[HypocriticalHumor even though he says it all the time]].
* PyrrhicVictory: [[spoiler:He agrees to spare the life of Stinkmeaner's clone to finally gain peace of mind, only to have Stinkmeaner II pester him 24/7 outside of his house.]]
* RedOniBlueOni: Red to Tom [=DuBois=]'s Blue
* RefusalOfTheCall: In Season 4, it is revealed that Robert was drawn into the Civil Rights movement against his will after accidentally getting on a bus full of Freedom Riders whilst escaping from a bus station attendant [[spoiler:for using (and messing up) a white men's restroom.]] He was actually attempting to ''escape'' the South and return to Chicago. Once he was on the bus, despite his vehement protests, the protest leader wouldn't let him off, insisting that his people needed him.
* RichesToRags: He was never super wealthy, but was implied to have enough savings and presumably a pension to live quite comfortably in the suburbs as well as constantly going on dates. [[spoiler:In season 4, it turns out the Freemans are now bankrupt, and most of the episodes, so far, have involved Robert participating in a bunch of harebrained schemes in order to clear his debts.]]
* ScatterbrainedSenior: One interpretation of his tall tales is that he is suffering from the early stages of dementia.
* TheScrooge: We don't know exactly how much he's good for, but he's incredibly cheap nevertheless. This is perhaps best demonstrated when he fired the only babysitter capable of handling Huey and Riley just because she left the lights on in the kitchen and used the telephone for five minutes.
* SelfServingMemory
* ShipperOnDeck: Granddad seems to ship Huey with Jazmine, and Riley with Cindy; either subconsciously (calling Jazmine Huey's "little friend", and dreaming of Jazmine instinctively hugging Huey when attacked by the swarm of Stinkmeaners), or intentionally (worrying that Riley might be gay, he invited Cindy to play with him).
* SkewedPriorities: This is a common joke with him. For example, when the Stinkmeaner-possessed Tom is choking him, Riley tries to save him by breaking several vases over his head. Granddad is just mad that Riley broke the vases.
** And later during that same night, Granddad is more focused on his date with a woman, than figuring out what to do with Stinkmeaner-Tom (who's been chained to a bed upstairs).
* SpotlightStealingSquad: Season 4 seems to be solely based around Granddad's personal issues, with Huey only getting a few lines each episode.
* TheStoner: In "Mr. Medicinal" he starts using marijuana, until two convictions, house arrest, and being forced to do an anti-drug PSA as community service force him to stop.
* TechnologicallyBlindElders:
** In the comics, Robert was browsing the Internet and was easily tricked into getting a computer virus.
** In the show, Robert doesn't understand the risks of dating websites, so he keeps meeting ugly and/or crazy women.
** In the episode "I Dream Of Siri", he visited an Apple Store and couldn't tell the difference between iPhones, iPads, and Macintosh laptops.
* TookALevelInDumbass: While Robert seemed to some common sense in the comics (except when it came to technology), in the show he's far more stupid and impulsive, a problem that seems to worsen with every season. Whenever there's anything involving money or women, he well jump into it without thinking of the consequences.
** In the Season 4 episode "Good Times", Ed II keeps tricking Robert into worsening his own debt, until he makes Robert sell himself into indentured servitude.
* UnreliableNarrator: It's unknown just how much of his alleged involvement in the Civil Rights Movement actually happened. Creator/WernerHerzog theorized that Robert might be a pathological liar or in the early stages of dementia.
* TheUnreveal: We never get to find out who his wife or child was.
* UnsympatheticComedyProtagonist
* VagueAge: How old is Robert anyway? It's not helped by the apparent ComicBookTime used by this franchise. If he's a WWII veteran, he would probably be in his 90s (as of the 2010s); although he still has prepubescent grandchildren.
** Creator/WernerHerzog also had trouble estimating his age, and gave a guess between 80-120.
* WhenAllYouHaveIsAHammer: With regard to parenting.
--> "You ever try beatin' his ass?"
* WhereDaWhiteWomenAt: Although Robert is usually seen dating black women, he's not picky about skin color.
* WouldntHitAGirl: He forbids Slickback from hitting Cristal in the Freeman house.

[[folder:Supporting Characters]]
!!Michael Caesar
->''"Remember, the people you want to liberate are still tied to the system. You need big distribution - make it hip. [...] [[HilariousInHindsight And make it]] [[{{Animesque}} look kinda anime]], like {{Anime/Pokemon}}: That's popular."''

Huey's best friend in the comic strip, [[AdaptedOut but is glaringly absent from the animated series]]. He's a smart-mouthed black kid from Brooklyn, UsefulNotes/NewYorkCity who chats with Huey about everything from politics to pop culture (mostly the latter, as they have a shared hatred of bad black media).
* AdaptedOut: Possibly due to Huey not entirely needing a {{Foil}} for much of the show's run, he has yet to appear thus far.
* BlackAndNerdy: Has just as much casual nerdy knowledge as Huey.
* CatchPhrase:
** "BROOKLYN!", at least when he was first introduced.
** Also his many YourMom jokes.
* CelebCrush: Claimed Creator/JenniferLopez was the female ideal of unobtainable beauty and then dumped her off the list because of the movie ''Film/{{Enough}}''.
* ClassClown: He blurts out random jokes to annoy Mr. Petto.
* TheConfidant: One of the people who will actually listen and care about what Huey has to say, lending an ear to his many conspiracy theories and potentially unpopular opinions, even if he'd rather be doing something less weighty.
* TheConscience: He serves this function particularly when Huey's thoughts or actions threaten to cross a line in some way, reminding him that life doesn't have to be so [[BlackAndWhiteMorality black and white]].
** A more straight-forward example of Caesar playing the part was when Huey tried to write a civil, courteous letter to President G. W. Bush. Whenever he'd type something cynical or rude, Caesar'd steer Huey back in the 'right' direction.
---> ''(Huey begins typing the header to his letter)''
---> '''Caesar:''' Start over.
* DeadpanSnarker: Mostly to Huey.
* DreadlockRasta: Caesar falls into the laid-back, anti-authoritarian group of dreadlock wearers, contrasting his best friend's ultra-serious, militant attitude and afro.
* {{Foil}}: Was introduced as a character with Huey's views and wisdom who was much more laid back about it. This quickly put him into the OnlySaneMan slot.
* FishOutOfWater: Same as the Freeman kids, though he gets used to it a lot faster than either of them do.
* TheGadfly / {{Troll}}: Though he's usually more generally sarcastic, he sometimes clearly says or does certain things just to get a rise out of Huey - sometimes to make a point, sometimes for fun, and it isn't always clear which.
* GenreSavvy
* InnocentProdigy
-->'''Caesar:''' [[LampshadeHanging Not to change subjects, but...]] [[NonSequitur Why are all the cookies on your side of the table?]]
* TheLancer: Caesar functions as Huey's right-hand-man on many an activity, such as being a co-founder to their newspaper. [[{{Foil}} At the same time, he generally challenges the kid's serious nature with a much warmer personality]].
* LastNameBasis: His first name, Michael, is referenced less than a handful of times in the comic strips.
* MeaningfulName: MC.
* MetaGuy: He has a habit of vaguely referencing he and Huey's position as characters, the comic's creator, or the strip itself in meta fashion.
-->'''Caesar:''' Can you believe it's been four years since the last [election]?
-->'''Huey:''' Yeah.
-->'''Caesar:''' Funny. Seems like we haven't aged a day...
* NiceGuy
* ObligatoryJoke: Often, much to Huey's annoyance. Especially since his jokes can come out of [[NonSequitur nowhere]] with little-to-no prompt.
* OnlySaneMan: Despite his similar views to Huey's, Huey's serious, mature, politically sapient, and borderline militant persona overlaps Ceaser's more laid-back and anti-authoritarian personality.
* RedOni: Red to Huey's blue.
* SoUnfunnyItsFunny: Most of his jokes fall into this category.
* WhereDaWhiteWomenAt: [[http://www.gocomics.com/boondocks/2010/10/03/ Oh Caesar.]]
* WideEyedIdealist: He's an optimist and tries to make Huey see the bright side of things.
* WiseBeyondTheirYears: He is categorized this to an extent. His awareness of the absurdities of society matches Huey's, but he still has a childish persona.
* YouNeedToGetLaid: To Condeleeza Rice of all people.

!!Uncle Ruckus (No Relation)
->''"There are those of you who say I'm wrong for hatin' niggas. I call y'all ALL hypocrites 'cause each and every one of you can name ten niggas you hate right now if you had to!"''
-->'''Voiced by:''' Gary Anthony Williams

A fat and old black man who seems to [[WhyDoYouKeepChangingJobs work in every conceivable low-wage job]]. [[BoomerangBigot Despite his ethnicity, he is also a loud-mouthed white supremacist]].
* AesopAmnesia: Whenever it occurs to him that he can be less racist, he forgets all about it.
* ArsonMurderAndJaywalking: Being the [[BoomerangBigot type of man he is]], his three favorite movies are ''Film/BirthOfANation'', ''Film/GoneWithTheWind'', and, well, ''Film/NottingHill''.
* {{Badass}}: In one episode, he's shown matching Huey in martial arts skills, which would arguably make him one of the most skilled fighters in the show. In spite of this, he holds that blacks are ultimately inferior in combat to whites.
** However he gets severely beaten up by the Hateocracy. But of course, they did outnumber him.
* BeenThereShapedHistory: He was in [[http://en.wikipedia.org/wiki/Freedom_Riders#Mob_violence_in_Anniston_and_Birmingham Birmingham, Alabama]] when the Freedom Riders stopped over there.
* BigBad: Can take this role in a few episodes, such as "Or Die Trying".
* BoomerangBigot: The whole purpose of his character. Uncle Ruckus is always praising white people and detesting black people, despite ironically being the latter. However Ruckus often denies being black, so from his point of view he isn't the hypocrite that he really is.
* BringMyBrownPants: In "The Story Of Gangstalicious", while at gunpoint.
-->'''Uncle Ruckus:''' (Calmly) Say that again? I couldn't hear you over the sound of me shittin' myself.
* ButNotTooBlack: Despite having the darkest skin of all characters, Ruckus ''really wants to believe'' that he isn't a black man. He often claims to be a white man with a "re-vitiligo" disease that darkens his skin.
* CallingTheOldManOut: He does this to his father Mister Ruckus in the climax of "The Color Ruckus".
* CanonImmigrant: He was originally created for the show, but [=McGruder=] added him to the comic in the brief period between the show starting and the comic ending.
* CatchPhrase:
** He introduces himself as "Uncle Ruckus, no relation."
** He also claims that "I've got re-vitiligo (it's the opposite of what Creator/MichaelJackson's got)."
* ChangelingFantasy: In "The Color Ruckus", we learn that Ruckus believes he's a white orphan with re-vitiligo, who was raised by a black family. It turns out that his black family is his real family, and his mother lied and made up this story to make him feel special. Even after his father broke the news though, Ruckus continued to be in denial about it.
* CharacterizationMarchesOn: Season 1 actually has moments where he seems completely aware that he's black. Referring to whites as "they" and blacks as "we" is a subtle example.
** Other lines include "I was happy at the back of the bus" and "I would have shoot you myself but I realized the white man got better aim." Not to mention the episode "The Passion of Reverend Ruckus".
* [[{{Cult}} Cult Leader]]: In one episode, he starts his own racist offshoot of Christianity, promising anyone who converts to white supremacy ([[BoomerangBigot even if they're non-white like him]]) that they can go to "White Heaven", an afterlife ruled by RonaldReagan.
** Later, we see him as an exorcist who specializes in dealing with evil black spirits such as Stinkmeaner (though he didn't actually know what he was doing).
** Later, he's the priest at Robert's aborted wedding to [[spoiler:Siri]].
* DeepSouth: Uncle Ruckus seems to hail from this region, as he speaks with a very thick Southern US accent. He's old enough to remember Jim Crow segregation, which is obviously something he fondly reminisces about a lot.
* DependingOnTheWriter: Either Ruckus is aware that he's black, or he's under the delusion that he's actually white. Ruckus would soon accept the latter belief.
* TheDragon: To Ed Wuncler II in Season 4. He is hired as an overseer at Freedomland, enthusiastically lording over the slaves. For some odd reason though, he doesn't object to Wuncler enslaving white people as well.
** In a flashback to the Freedom Rides of 1961, he helps out [[http://en.wikipedia.org/wiki/Bull_Connor Bull Connor]] by rallying a racist white mob, and planting a bomb on the Freedom Rider bus set to explode if it exceeded over 15 MPH.
* EnemyMine: [[http://www.youtube.com/watch?v=5ijFSU1S-3g Briefly formed one with black people in order to finance his movie.]] [[note]]However Aaron [=McGruder=] failed to get funding for an Uncle Ruckus movie.[[/note]]
* EvenEvilHasLovedOnes: He's on very good terms with his mother and brothers; it's his father and grandmother he hates ([[AbusiveParents with good reason]]).
* EvenEvilHasStandards: It's shown in "The New Blacks" that he considers mocking or abusing the disabled to be inexcusable.
* EvilOldFolks / GrumpyOldMan
* FatBastard / FatIdiot
* FreudianExcuse: Was raised by an extremely abusive dad who always proclaimed his hatred of white people, as well as a loving mom who idolized Caucasians (and lied that Ruckus was born white). This helped warp Ruckus' mind into the self-hating oaf we know, love, and hate.
* FriendlyEnemy / TheFriendNobodyLikes / VitriolicBestBuds: Sometimes he's this with Robert and Tom. Despite his racist views and the verbal abuse they keep slinging at each other because of it, the three sure seem to hang out a lot.
** For some reason, Ruckus tolerates Robert and plays board games with him at the park, although Ruckus shows open disdain for his grandsons (by refusing them entry into the school bus).
** Not surprisingly, Ruckus respects Tom for being an "Oreo" and sharing the same [[WhereDaWhiteWomenAt preference for white women]].
** For some reason though Ruckus throws all respect completely out the window by Season 4, especially in "Freedomland", as Tom and the Freemans are working as slaves in the titular theme park.
* GoMadFromTheRevelation: In "The Uncle Ruckus Reality Show", he goes through a DNA test. Ruckus reads the results and finds out that he's 100% African, much to his shock and horror. After Ruckus' unsuccessful [[DrivenToSuicide suicide attempt]], the show's producer forces the geneticist into redoing the DNA test, so that Ruckus is "actually" 50% Caucasian and he snaps back to normal.
* {{Gonk}}: He's old, obese, balding, and has a bulging eye and crooked teeth.
* HilariouslyAbusiveChildhood: Played for laughs and drama.
** [[AbusiveParents Abusive Dad]]: Well, they ''try'' to play it for laughs, but it's not very funny to see how brutally abusive his dad was. He beat the shit out of him ''for having fun and wanting to be a doctor''. No wonder he grew so messed up.
* HisNameReallyIsBarkeep: When they flashback to his childhood, his mother actually calls him Uncle, so "Uncle Ruckus" is actually his full name. It's revealed in "The Color Ruckus" that he's named after his father's uncle. Yes, both the Uncle and the Ruckus part.
* HorribleJudgeOfCharacter: His hatred of blacks and blind love of whites. Not to mention his mother. Not that he could see it anyways.
* HypocriticalHumor: Due to his BoomerangBigot personality.
* IKnowKarate: "You think you're the only one to master the ancient and deadly art of the Nunchaku?"
* {{Jerkass}}: Most of the time. He often takes any opportunity to degrade other blacks.
** JerkWithAHeartOfGold: At times, such as "A Huey Freeman Christmas" and "The Color Ruckus", show that he does have a more decent side.
* LargeHam
* LaughablyEvil
* {{Leitmotif}}: [[ReturnOfTheJedi Jabba's theme]] plays most of the time he's on-screen from Season 2 onward.
* MadEye: Interestingly enough, this is the only one with color.
* MeaningfulName: ''Uncle Ruckus'' is a combination of [[Literature/UncleTomsCabin Uncle Tom]], [[Film/SongOfTheSouth Uncle Remus]], and Amos Rucker (allegedly a slave soldier who fought for the [[UsefulNotes/AmericanCivilWar Confederacy]]), creating a black man most enthusiastically subservient to white people.
* NWordPrivileges: No one takes offense to his song "Don't Trust Them New Niggas Over There" in "The Garden Party", or anything else he says because he has these.
-->'''White party guest:''' I think the "N-Word" is okay if ''they'' say it.
* NotSoHarmlessVillain: Occasionally, Ruckus proves to be more than just a hateful oaf:
** He's mastered using nunchucks, and even beats ''[[AfroAssKicker Huey]]'' in a fight.
** He becomes Ed Wuncler II's right-hand man, and takes his harassment of the Freemans to whole new levels.
** Even way back during the era of Jim Crow South, Uncle Ruckus supported racist mob violence.
* PassFail
* PetTheDog: In "A Huey Freeman Christmas", he comforts Jazmine about Riley's assaults on a MallSanta.
* PoliceBrutality: In "The Block Is Hot", Ruckus calls the police, but they shoot in his direction, and when that doesn't work they beat him with batons. But Ruckus, being Ruckus, actually isn't bothered by this abuse, and he even joins the police force so he can fulfill his desire to do the same to other black guys!
* PoliticallyIncorrectVillain: If you didn't already know, Ruckus is very racist against pretty much anyone who isn't of non-Hispanic white European descent; Africans, Chinese, Mexicans, Arabs, etc.
** However he doesn't seem to have much ill-will towards multiracial people who are part white, such as Jazmine; Ruckus himself seems to be satisfied if someone else lied that he's 50% Caucasian.
** And as seen in "The New Black" he's also homophobic, remarking that he doesn't even respect gay white people.
* SitcomArchnemesis: Ruckus is usually just an annoying jerk and idiot. But see NotSoHarmlessVillain above.
* StrawCharacter: Uncle Ruckus is a satirical spoof of white supremacists and Tea Party conservatives.
* VillainProtagonist: Of "The Passion of Reverend Ruckus", "The Uncle Ruckus Reality Show", "The Story of Jimmy Rebel", and "The Color Ruckus".
* WhereDaWhiteWomenAt: Obviously Ruckus doesn't like black women [[spoiler:(except for Ebony Brown)]], and views whiteness as ideal beauty. He considers Tom lucky for marrying Sarah.
* WhyDoYouKeepChangingJobs: Subverted. He's holding down ''at least 30'' different jobs ''at once''.

!!Jazmine [=DuBois=]
-->'''Voiced by:''' Gabby Soleil (Seasons 1-3), Kiarah Pollas (Season 4)

The biracial daughter of Tom and Sarah [=DuBois=]. While Huey finds her to be naive and annoying, she becomes his only friend in the TV show.
* AccidentalPervert: Poor Jazmine. The first penis she saw belonged to an 80+ year-old man.
* BreakTheCutie: A major reason Huey has for talking to her in the comics, though he doesn't exactly mean to be malicious; he truly thinks she would be better off if she were a cynic like him, so he makes it his mission to tear down her childish beliefs.
* ButtMonkey: In the comic, though she only tends to be treated badly by Huey and occasionally Riley. It seems like, in general, the world enjoys messing with her naivete. In the show, she's more TheChewToy since Huey is a lot less abrasive.
* ChildrenAreInnocent: In the sense of being both naive and good-natured. She also doesn't like it when others drag her into trouble.
* DemotedToExtra:
** In the comics, she has a greatly diminished role after Huey meets and befriends Caesar. [[ChuckCunninghamSyndrome She even has a two-year absence]] before she reintroduces herself.
** In the first two seasons of the show, she would regularly interact with the main characters and even be the focus of a few episodes and plots. In the last two seasons, she's lucky to ever get a line.
* {{Fangirl}}: Of Music/{{Usher}}.
* FanOfTheUnderdog: It is no coincidence that she trusts Huey in spite of him being a {{Jerkass}} to her. It is especially prevalent in Season 3 as she is the only person who actually listens to him and has spoken highly of him when even the President of the United States has denounced him.
* FishOutOfWater: In the comics. Like the Freemans, her family are newcomers to Woodcrest (where from, she doesn't say). Jazmine also doesn't know how to fit in with black or white people.
* FunnyAfro: Has a huge afro several times bigger than Huey's. It makes her insecure. {{Played for laughs}}, naturally.
* GranolaGirl: Implied. In "The Fried Chicken Flu", she didn't jump on the KFC bandwagon that was sweeping the nation because "fried chicken is murder". In "The Fundraiser", she [[spoiler:donates most of the money she made with Riley to [[AnimalWrongsGroup PETA]], much to his dismay]].
* {{Hikikomori}}: Once she returns in the comic strip, her two-year-long ChuckCunninghamSyndrome is explained as her locking herself in her room ever since 9/11 out of fear of terrorists.
* LiteralMinded / SarcasmBlind: Extremely so in the comic, to the point where Huey can say almost anything to her and she'll take it at face value. This combined with her WideEyedIdealist traits make her ''extremely'' gullible (and as a {{running gag}}, very bad at YourMom jokes).
* LuminescentBlush: At the end of "Wingmen".
* MixedAncestry: Particularly in the comics, being a mulatto gave her a lot of personal confusion. Downplayed in the show though.
** To be precise, through her mother's side she is Irish, Swedish, and German; and through her father's side she is African, Cherokee, French, and Scottish.
** Besides the puffy afro hair texture and slightly tanned skin, she could probably pass as white. Cindy didn't know Jazmine was part black until she was informed so.
* MoralityPet: Jazmine is this to Huey, which is weird as he is often the one to tear down any wide-eyed delusions she carries. But as soon as someone tries to exploit her or if she needs help, knowing that helping her would be at the expense of his own interests, Huey usually helps her out.
** The best example of this was when he tried to stop Ed I's scheme against Jazmine in "The Block Is Hot".
* NervousWreck: She probably got her insecurity from her father.
* NiceGirl: Her sweet nature never dies out despite all the negativity around her.
* ShipTease: It's implied that she may have a crush on Huey. It's most obviously suggested in two comic strips, one where she asks if anyone (like Huey) would ever marry her, and another where she gives him a Valentine's Day card. But Huey, not being the sentimental kind of person, seems [[ObliviousToLove oblivious to all of this]].
* SignificantGreenEyedRedhead
* [[TokenWhite Token Half-White]]
* VitriolicBestBuds: In a one-sided way with Huey, who is much ruder to her.
* VocalEvolution: Justified, since her voice actress was a little girl when the series began.
* WideEyedIdealist: To the point of naivety.

!!Thomas "Tom" Lancaster [=DuBois=]
-->'''Voiced by:''' Cedric Yarbrough

[[TheWhitestBlackGuy A black man who "acts white" as much as possible]]: He's an IvyLeague-educated attorney, [[WhereDaWhiteWomenAt married to a white woman]], and has no "ebonic" accent. A {{nice guy}}, but also a [[ButtMonkey big]] [[ExtremeDoormat pushover]].
* ApologizesALot: Something which causes Sarah to explode on him in "Pretty Boy Flizzy".
* BerserkButton: Anyone who wants to violate his anus, tries to take his wife, or acts inappropriately in front of his daughter.
* ButNotTooBlack: "[[LampshadeHanging Well, actually, I'm more of a]] [[StarbucksSkinScale caramel complexion]]."
** According to a DNA test, Tom is 32.5% Scottish. This would also make his daughter mostly white.
* ButtMonkey / ExtremeDoormat: The guy has practically NO backbone! He gets very little respect from his friends (and at times, even his wife).
* CharacterDevelopment: Tom starts branching out from a prosecutor who just does his job, to a defense attorney that takes cases based on innocence of the client, regardless of the money he's offered. He's also become less of a doormat as he is more prone to swearing when he's angry and calls people out when he feels disrespected.
* ClusterFBomb: In "Ballin'" and "Home Alone".
* CrouchingMoronHiddenBadass / TookALevelInBadass:
** In "A Date With The Booty Warrior". He was still cowardly for much of the episode, but he was able to [[spoiler:overcome his fears about rape, and defeat the Booty Warrior]].
** By the end of "Pretty Boy Flizzy", he seems to have grown more of a spine, [[spoiler:and resolved most of his marital hang-ups with Sarah]].
* DeadpanSnarker: In the comics, he was actually a bit less nice and sometimes made snarky comments. This trait didn't carry over to the show.
* EvenTheGuysWantHim: Much to his dismay.
* FreudianExcuse: The source of his PTSD-like phobia of prison rape comes from merely watching a movie about it as a kid, rather than actually experiencing it.
* TheFriendNobodyLikes: To a lesser extent than Ruckus, but his straight-laced and needy demeanor has occasionally made the Freemans reluctant to deal with him.
* HenpeckedHusband: He feels very insecure around his wife, who in turn feels frustrated by his submissive behavior.
* InelegantBlubbering: Whenever he's forced to confront his fear of prison. A manly crier he is not.
* IntergenerationalFriendship: With Huey and Robert.
* LovableCoward / NervousWreck: He cries and panics very easily, especially when it comes to marital problems or his phobia of rape.
* MeaningfulName: ''Tom'' as in Uncle Tom, ''[=DuBois=]'' from W.E.B. [=DuBois=].
* NiceGuy: He's usually a pleasant neighbor and family man.
** BewareTheNiceOnes: Although over the course of the television series, he does grow more irritable due to all the shit that happens to him.
*** In the comic strip he's a bit less of a nice guy. He had a heated conflict with his wife because they voted for different presidential candidates, and he even called her a hussy!
* NWordPrivileges: Averted, as he and his daughter are the only members of the black cast who don't say "nigger" or any of its derivatives.
** But of course Stinkmeaner has no problem with the word, so while controlling Tom's body, he embarrasses him by making him drop some N-bombs out loud in a courtroom.
* PrisonRape: He has an obsessive and paranoid phobia of going to jail and getting anally raped. The result is that he tries to avoid committing any kind of crime no matter what. The cost is that his wife is too sexually frustrated as a result.
* ProperlyParanoid: In "A Date With The Booty Warrior", the moment he decides to visit prison, he really is being stalked by a deranged rapist! [[spoiler:Fortunately, Tom manages to literally save his own ass from the Booty Warrior during a fight.]]
* RedOniBlueOni: Tom is the Blue to Robert and Huey's Red.
* StrawCharacter: He and his wife are stereotypical clueless moderate liberals. Although they almost split in one comic arc, because he voted for Al Gore instead of Ralph Nader like Sarah did.
* WhereDaWhiteWomenAt: In the comics, he is stated to have only dated white women, eventually marrying Sarah. While talking to her about his preference in women, he even [[TropeNamer quotes the famous line word-for-word]] from ''Film/BlazingSaddles''.
* TheWhitestBlackGuy: Sometimes Huey forgets to count Tom as a black man.
* WouldntHitAGirl: Something A Pimp Named Slickback calls him out on in a SpoofAesop.

!!Sarah [=DuBois=]
-->'''Voiced by:''' Jill Talley

A white woman, who is Tom's wife and Jazmine's mother. Her marriage with Tom gets strained because of politics (in the comics) and his phobia of rape (in the show).
* AllGirlsWantBadBoys: She wishes that Tom was more assertive and dominant, and less of a pushover.
* ArtEvolution: Her hair was originally straighter and shorter.
* {{Fangirl}}: Of Music/{{Usher}}, UsefulNotes/BarackObama, and [[{{Expy}} Pretty Boy]] [[Music/ChrisBrown Flizzy]].
* [[HenpeckedHusband Henpecked Housewife]]: She is often pretty frustrated by Tom's uptightness and awkwardness in public. His obsessive phobia about {{prison rape}} has taken a toll on their marriage.
* MasculineGirlFeminineBoy: Sarah and Tom respectively. While Sarah isn't a tomboy by any means, she would at least seem so in comparison to her very unmasculine husband. She's frustrated that he isn't the dominant spouse.
* ThePiratesWhoDontDoAnything: Sort of. In the comic strip she's also an attorney like Tom, but in the TV series she seems to just be a housewife.
* SatelliteCharacter: She's Tom's wife, Jazmine's mother, the Freemans' neighbor, and every episode she's featured in deals with one of those facts.
* StrawCharacter: She and her husband are stereotypical clueless moderate liberals. Although they almost split in one comic arc, because she voted for Ralph Nader instead of Al Gore like Tom did.
* TokenWhite
* TookALevelInJerkass: To a major extent in "Pretty Boy Flizzy", where her previous frustration at Tom's stuffiness is exaggerated to unreasonable demands and full-blown self-centered mood-swinging. Likewise, her wandering eye is ramped up to the point of throwing herself at other men and putting down Tom in front of her daughter (though granted, that was while drunk).
** JerkWithAHeartOfGold: But at the end of the episode, she apologizes to Tom for pushing him around earlier.
* [[WhereDaWhiteWomenAt Where Da Black Men At]]: In the comics, she only dated black men, eventually marrying Tom. She's still openly attracted to other black men, much to Tom's dismay.
* YourCheatingHeart: Subverted. Although Sarah flirts with other men (Usher, Obama, Flizzy) in front of Tom, she never actually commits adultery.

[[folder:Recurring Characters]]
!!Colonel H. Stinkmeaner
-->'''Voiced by:''' Cedric Yarbrough

An old and blind black man with a sadistic sense of humor. He starts a legendary feud with Robert Freeman, which results in his accidental killing of Stinkmeaner during a street fight. Afterwards though, Stinkmeaner escapes from Hell and haunts Robert as a ghost. He later gets cloned for some reason.
* AnAxeToGrind: Uses this while in Tom's body to try to kill Granddad.
* AssholeVictim: When Granddad accidentally kills him. Lampshaded when Huey states that the world is probably better off without him, even though the Freeman family mourn him anyway.
* BackFromTheDead: Sort of happened once when he possessed Tom, but now Season 4 has confirmed that he is indeed back ''again'' via cloning.
* {{Badass}}: Well sort of...
** HandicappedBadass: Subverted in his first appearance. When Stinkmeaner trips Robert and beats him with his cane, Huey assumes that he must be some kind of [[DisabilitySuperpower blind yet talented martial artist]]. It turns out that Stinkmeaner was just lucky that time, as during the second fight he stood no chance at all against Robert.
** LikeABadassOutOfHell / TookALevelInBadass: However while Stinkmeaner was damned in Hell, he ''literally'' took TrainingFromHell and learned how to fight an army of demons. The Devil was so impressed that he releases him from Hell for revenge. So when he possesses Tom's body, he proves to be a capable threat to the Freemans.
*** Later, his clone seems to not only be an expert martial artist as well, but also possesses enhanced strength.
* BedTrick: Sort of. While he was possessing Tom, he took advantage of it by [[WhereDaWhiteWomenAt having sex with Sarah]], who was oblivious about why her husband was acting so strange.
* BlindBlackGuy: He became blind due to cancer in his adolescence, but he didn't consider it a big loss, because he never appreciated looking at beautiful sights such as sunsets and rainbows.
* BloodKnight: Really enjoys Nigga Moments.
* BoomerangBigot: While he hates everyone, he hates black people slightly more than everyone else.
* CameBackStrong: Initially just a hateful old man who managed to get lucky in a single fight. When he comes back from Hell, though...
** His clone is even stronger.
* CardCarryingVillain: He doesn't outright call himself evil or a villain, but he seems very proud of his reputation as an asshole.
* CatchPhrase: His preferred insult is any variation on "[[ThisIsForEmphasisBitch Bitch-Ass]] [[NWordPrivileges Nyukka]]!"
* CloningBlues: Subverted, as his clone doesn't really feel any different knowing he's a clone, only that he's alive and the other guy is dead. Though the clone is confused as to why he's an old man biologically, despite only being a few years old chronologically.
* DemonicPossession: Stinkmeaner's ghost rises out of Hell to possess Tom. And then Ruckus attempts an exorcism on him.
* TheDeterminator: Not even death could stop his nigga moment (something that [[InLoveWithYourCarnage he enjoys]]), but peace and/or jail time will.
* DidYouJustFlipOffCthulhu: Stinkmeaner called {{Satan}} himself a "bitch-ass nigga".
* DrivesLikeCrazy: [[SarcasmMode In his defense]], have you tried driving while blind?
* EvilCripple: He doesn't care that driving while blind may endanger innocent bystanders.
* EvilIsHammy: It's especially hilarious when his spirit possesses the far more mild-mannered Tom.
* EvilOldFolks / GrumpyOldMan / ScrewPolitenessImASenior: Though he was just as nasty when he was young.
* ForTheEvulz: The sole motivation behind his ''very breathing''.
* GoodIsBadAndBadIsGood: He believes that witnessing bad things happening to others is what makes life worth living.
* {{Gonk}}: Not as ugly as Ruckus, but still ''pretty ugly''.
* [[HatesEveryoneEqually Hates Everyone Almost Equally]] / MisanthropeSupreme: Stinkmeaner is a misanthrope who hates everybody, including people of all races, [[BoomerangBigot but black people especially]]. And the closest thing that Stinkmeaner ever had to a circle of friends were the Hateocracy, but he admits that he only hated them slightly less than everyone else.
* HellOfATime / TrainingFromHell: ''Literally''. Stinkmeaner doesn't seem to be very bothered by his eternal damnation, and in fact he enjoys spending his time in Hell by learning martial arts, beating up lots of demons, and preparing for his revenge on Robert Freeman. He at least finds Hell to be preferable over [[FateWorseThanDeath jail]].
* {{Jerkass}}: The biggest example in the series. He puts Ed Wuncler to shame.
* LaughablyEvil: He may be one of the biggest assholes around, but he sure is hilarious to watch.
* NightmareFuelStationAttendant
* NWordPrivileges
* {{Our Demons| Are Different}} [[OurGhostsAreDifferent and Ghosts Are Different]]: Stinkmeaner's disembodied soul can qualify for both.
* ThePowerOfHate: He owes his long life to his "love of hatred". It's also what allows him to return ''from the afterlife'' to continue his Nigga Moment. Later, it turns out that the only way to exorcise Stinkmeaner's ghost out of Tom is [[spoiler:tricking Stinkmeaner into bonding with Ruckus over their shared {{Boomerang Bigot}}ry; because a Nigga Moment will end should it turn peaceful]].
* RoaringRampageOfRevenge: When Stinkmeaner's soul escapes from Hell, he plans to get back at Robert by murdering him, but first he trolls a lot of people along the way.
** Subverted with Stinkmeaner's clone, who never knew the original Stinkmeaner nor Robert Freeman. The clone just thinks his only purpose in life is to be as annoying as his predecessor.
* {{Sadist}}: He lives for making others suffer.
* TheSociopath: While narrating his backstory, Huey makes it clear that Stinkmeaner was always rotten and never cared about other people.
* {{Troll}}: What he does for a living.
* WouldHurtAChild: Had no problem fighting Huey and Riley when they tried to exhort his spirit out of Tom.

!!Edward "Ed" Wuncler I
-->'''Voiced by:''' Creator/EdwardAsner

Ed Wuncler I is the wealthiest businessman in Woodcrest. [[CorruptCorporateExecutive Not surprisingly, his greed and amorality are insatiable.]]
* AristocratsAreEvil: His family has controlled Woodcrest since the 19th century, maintaining a tight economic stranglehold on the city.
* BadBoss: Not surprisingly, he treats his employees like crap.
** He arbitrarily fired the entire staff of a restaurant, except for the illegal immigrants from Mexico.
** He proudly exploits child labor, whether it's outsourced to a foreign sweatshop, or even Jazmine's lemonade stand at home.
** He orders the murder of a kickball referee, because he accepted bribes from the Chinese team instead of Wuncler himself.
** And he almost got Dan the security guard murdered, as part of a convoluted plot to profit from his death.
* BaldOfEvil: Partially bald, but close enough.
* BigBad: Due to being the most powerful villain in the show, although he's only the antagonist of some few episodes.
** BiggerBad: Well he is the man behind his son and grandson, who are also crooks just like him.
* BitchInSheepsClothing / FauxAffablyEvil: He can be very polite, especially to Robert Freeman. He still has zero qualms about cruelly manipulating other people for his own greed.
** The best example of this is when he tricks Jazmine into selling her lemonade stand to him, while promising her a pony. He then orders her to work like a sweatshop laborer, while using loopholes to avoid paying his end of the bargain.
* TheChessmaster: He relies on sheer cunning instead of being crazy like the other bad guys on the show.
* CorruptCorporateExecutive: He owns most of Woodcrest, including the authorities.
* DoesThisRemindYouOfAnything: His business tactics in "The Itis" are deliberately played as using drugs and crime to drive down property values on desirable locations.
* EnemyMine: In "The Red Ball", Huey has no choice but to participate in Wuncler's kickball game, due to everyone's property being at stake.
* EvilOldFolks: Old enough to have an adult grandson.
* EvilPlan: Hatches a few, usually involving money.
* {{Expy}}: Lampshaded InUniverse, where he is described as a [[WesternAnimation/TheSimpsons Mr. Burns knockoff]].
** Also if Ed III is UsefulNotes/GeorgeWBush, this would naturally make his grandfather Ed I, Prescott Bush. Though, ''Wuncler's'' grandfather was Prescott Rothchild Wuncler.
* FatBastard: He personifies the "fat cat capitalist".
* ForTheEvulz / OnlyInItForTheMoney: Wuncler is probably the richest, most powerful man in the country, but he'll ''still'' pull many messed-up scams and crimes to get more cash. Because shit, you can never have enough, right?
* InkSuitActor: Imagine Ed Asner still channeling [[TheMaryTylerMooreShow Lou Grant]], and you wouldn't be too far off.
* {{Jerkass}}: Wuncler has done multiple acts of pure malice throughout the series and he is proud of them.
* KarmaHoudini: [[spoiler:You know you're one when even '''the President''' ''personally phones'' the agent holding you at gunpoint to tell him to stand down.]]
* MeaningfulName: His name refers to the Once-Ler from Dr. Seuss' ''Literature/TheLorax'', who was just as greedy as he is.
* PoliticallyIncorrectVillain: He is racist against Arabs.
* [[ScrewTheRulesIHaveConnections Screw The Rules, I Have Connections]] [[ScrewTheRulesIHaveMoney and Money!]]: His family is stated to have easily bribed the [[DirtyCop local police department]]. And they even have immunity from the ''federal government''.
* TheSociopath: Will do anything to get more cash.
* StrawCharacter: Some of his rhetoric seems to be conservative/libertarian-based. Since he is a satiric characterization of Prescott Bush, it is kind of expected.

!!Edward "Ed" Wuncler II
-->'''Voiced by:''' Sam [=McMurray=]

Ed Wuncler II is the son of Ed I, and father of Ed III. The main antagonist of the Season 4 story arc, he's a loan shark who only worsens Robert's bankruptcy.
* AnAxeToGrind: Tries to cut off Huey's legs with an axe to make a public example.
* BigBad: Of Season 4.
* BitchInSheepsClothing / FauxAffablyEvil: Barely hides his malice toward his debtors behind a smile and is implied to kill those who make him too angry. He also cares little about actually getting the debt paid off, opting to trick his debtors into further debt or more serious binding contracts to wring out every penny he can get from them.
* BerserkButton: Do not owe him money.
* CompositeCharacter: He possesses the business-driven attitude and mannerisms of his father. He also possesses characteristics of his son, such as engaging in petty thievery and tendency to commit impulsive acts of violence.
* CorruptCorporateExecutive: Like father, like son.
* DisposingOfABody: Leaves one in the Freemans' garage and implies this is the type of work that Robert Freeman will do for him.
* EqualOpportunityEvil: Sort of, in his own twisted way. The Freedomland slaves consist of both black and white people.
* EvilerThanThou: Actually manages to be ''worse'' than his father in Season 4, his business practices and forcing people in debt to him to [[spoiler:sign themselves into slavery]] makes anything Wuncler, Sr. did look like a girl scout patrol by comparison. He doesn't even care that much about collecting his debts; he just likes having people indebted to him.
* {{Expy}}: Continuing from his son and father, Ed II would be UsefulNotes/GeorgeHWBush.
* IndenturedServitude: He makes his debtors sign away their freedom to serve him, forcing them to role-play as slaves in a 19th century theme park.
* {{Jerkass}}
* KarmaHoudini: While his scheme to enslave his debtors is thwarted, he still manages to escape.
* TheGhost: Played with. Ed Wuncler, Jr.'s existence was implied because Ed Wuncler the III was Ed Wuncler's biological grandson. However, he finally makes an appearance in the fourth season.
* TheMafia: In contrast to his son's wannabe gangster attitude, Ed Wuncler, Jr. acts more like a "made man", showing up to places in a white suit and committing crimes well-associated with the Mafia such as extortion, loan sharking, and financial blackmail.
* NWordPrivileges: Gives himself these, since he's a Wuncler.
-->Robert Freeman, my nigga! Can I say that? Yes, I can!
* [[ScrewTheRulesIHaveConnections Screw The Rules, I Have Connections]] [[ScrewTheRulesIHaveMoney and Money!]]
* TheSociopath: An even worse one than his father.
* WhiteGangBangers: Though more like a mobster and less like a street gangster.
* WouldHurtAChild: Has no problem attempting to slice off Huey's legs simply for opposing his slavery park.

!!Edward "Ed" Wuncler III
-->'''Voiced by:''' Charlie Murphy

Ed Wuncler III is the youngest (and dumbest) member of the Wuncler clan. After returning from the [[UsefulNotes/WarOnTerror Iraq War]], he and his best friend Gin Rummy commit a series of petty crimes.
* AmbiguouslyGay: His friendship with Rummy sometimes comes off looking like a gay romance. This was lampshaded by Riley.
* AxCrazy: Mostly in terms of how he thinks outright sociopathic behavior is all in good fun.
* BringMyBrownPants: His time in Iraq... good God. To be precise, he soiled himself at least a dozen times, the other members of his unit called him "Stinkbomb", and he was eventually kept from joining on patrols because the enemy could smell him coming.
* CatchPhrase: "(What the) fuck y'all lookin' at?"
* ChuckCunninghamSyndrome / WhatHappenedToTheMouse: He's last seen in the Season 3 finale, [[spoiler:where he's being held hostage by Jack Flowers]]. We never know what happens to him, as he isn't seen or heard from at all in Season 4.
* ComedicSociopathy / LaughablyEvil: He isn't competent. It's surprising that he's even still alive. He's mainly dangerous because he's so wildly reckless with his weapons, and his grandfather bails him out of any possible incarceration.
* {{Evil|Redhead}} FieryRedhead
* {{Expy}}: Meant as a parody of UsefulNotes/GeorgeWBush, being destined for greatness simply because his family is rich.
* FailedASpotCheck: Ed takes this to truly impressive levels. While trying to kidnap Oprah, Ed assaults the wrong bookstore and mistakenly takes Maya Angelou, even though one had a large crowd of people outside and a large sign saying "Welcome Oprah". Another time, when Riley tries to get his help in dealing with a bully, Ed kidnaps the wrong kid... despite the fact that Riley gave him a picture.
* FearlessFool: He invites Riley to test his ballistic vest with live ammo while he's wearing it, wanders in full view through raging gunfights [[GunsAkimbo firing]] [[GangstaStyle wildly]] [[ATeamFiring at nothing]], and seems to forget that taking both hands off the steering wheel to shoot out of a moving car is a bad idea, among other things. He's really, ''really'' lucky to be alive at this point.
* IdiotHoudini / KarmaHoudini: Due to his grandfather's protection and being viewed as a SociopathicHero in-series.
** Possibly subverted in "It's Goin' Down", [[spoiler:where Ed III is last seen being held hostage by Jack Flowers]]. We don't know what happens to him afterwards.
* {{Jerkass}}: Hoo boy.
* MotorMouth: Nobody does rambling anecdotes quite like Charlie Murphy.
* NotSoHarmlessVillain: He may be a stupid and incompetent criminal, but that doesn't mean he's not dangerous, as he's still tried to shoot at people with lethal intent.
* NWordPrivileges: He and Rummy call each other "niggas" despite both of them being white.
* PocketProtector: His bulletproof vest and big "W" medallion has spared him from death on several occasions.
* PrettyFlyForAWhiteGuy / WhiteGangBangers: Despite being a rich white guy, he acts like a black gangster.
* PsychopathicManchild: He's a spoiled rich brat who doesn't have a real job, and instead he just spends his time committing armed robberies. Also when angered once, he shot up his {{PlayStation 2}} before his butler replaced it with another [=PS2=].
* RunningGag: Will generally find some way to get shot in the chest (surviving due to his vest).
* [[ScrewTheRulesIHaveConnections Screw The Rules, I Have Connections]] [[ScrewTheRulesIHaveMoney and Money!]]
* SeinfeldianConversation: Which he [[LampshadeHanging hangs a lantern on]].
* StupidCrooks / StupidEvil: Ed and Rummy usually botch their crimes hilariously. [[NotSoHarmlessVillain They still prove to be menaces to society though.]]
* ThoseTwoBadGuys: With Rummy.
* TooDumbToLive: But he always survives because of his {{bulletproof vest}} and [[IdiotHoudini idiot immunity]].
* TriggerHappy: He's often itching to unload his gun on something.
* UpperClassTwit: A good example of how money doesn't buy class.
* VillainWithGoodPublicity: In "A Date With The Health Inspector", Ed and Rummy get away with robbing a convenience store, because it seemed that the owners were terrorists (or were mistaken for terrorists, it wasn't made clear who they really were). They were painted as heroes afterwards.
* WouldHurtAChild: He's willing to kidnap and torture a kid if someone asks him to do it.

!!Gin Rummy
-->'''Voiced by:''' Creator/SamuelLJackson

Ed III's best friend. Much like him, he's an ex-soldier and a "wigger" criminal.
* AxCrazy
* AmbiguouslyGay: His friendship with Ed sometimes comes off looking like a gay romance. This was lampshaded by Riley.
* ChuckCunninghamSyndrome / WhatHappenedToTheMouse: Much like his best friend Ed III, he's nowhere to be seen in Season 4.
* ComedicSociopathy / LaughablyEvil
* {{Expy}}: Meant as a parody of Donald Rumsfeld.
* FeigningIntelligence: Well he is slightly smarter than Ed, though that's really not saying much.
* IdiotHoudini / KarmaHoudini: Same as Ed. Possibly subverted in "It's Goin' Down".
* MurderIsTheBestSolution: When Robert is trying to solve his problems about his alleged son Lando, Rummy keeps suggesting to kill him.
* NotSoHarmlessVillain: On one occasion, we get to see him kidnapping and murdering a crooked kickball referee on Ed I's orders.
* NWordPrivileges: He and Ed call each other "niggas" despite both of them being white.
* PrettyFlyForAWhiteGuy / WhiteGangBangers: Despite being a rich white guy, he acts like a black gangster.
* PsychopathicManchild
* [[ScrewTheRulesIHaveConnections Screw The Rules, I Have Connections]] [[ScrewTheRulesIHaveMoney and Money!]]
* SeinfeldianConversation: Which [[LampshadeHanging he hangs a lantern on]].
* SophisticatedAsHell
* StupidCrooks / StupidEvil: Ed and Rummy usually botch their crimes hilariously. [[NotSoHarmlessVillain They still prove to be menaces to society though.]]
* ThoseTwoBadGuys: With Ed.
* TooDumbToLive: But survives.
* TriggerHappy: He's often itching to unload his gun on something.
* UpperClassTwit: A good example of how money doesn't buy class.
* VillainWithGoodPublicity: See Ed III's example above.

!!Cindy [=McPhearson=]
-->'''Voiced by:''' Creator/TaraStrong

[[PrettyFlyForAWhiteGuy A little white girl obsessed with (very stereotypical notions of) black culture]]. In the comics, she tries to be friendly to Huey, but comes off as ignorant and annoying. In the show she becomes an exaggeration of herself, is more of a jerk, and befriends the like-minded Riley.
* AdaptationDyeJob: Similarly to Riley, her hair doesn't change color, but it does change styles from a single ponytail to a pair of giant braids. She keeps the HairAntennae, though.
* CharacterExaggeration: In the original comic, she was simply a white student obsessed with black culture and oblivious to Huey's blatant dislike of her. In the show, she's an over-exaggerated wigger.
* CheerfulChild: The comic version is easily excitable and cheery.
* ChildrenAreInnocent: In the comic strip only. She tries being nice to Huey, failing to realize that her wigger antics annoy him. She's also easily tricked by Riley, who takes advantage of her trusting nature.
* ChuckCunninghamSyndrome: Cindy only appeared in the comic strip for the first two years during the comic's lifespan. The other four years? She dropped off the face of the earth. She made her first appearance in seven years on the show, becoming a recurring character in the second and third seasons. She's absent from the fourth season though.
* DefeatEqualsFriendship / FireForgedFriends: With Riley in the cartoon. Even though Riley broke Cindy into tears with a YoMomma routine to beat her at basketball, they seem to have become friends in later episodes.
* TheDitz / DumbBlonde: Not very bright in the comic, especially when it comes to racial matters. An early RunningGag had Riley use her as a patsy or victim in his schemes, simply because she was so easy to fool.
** She is, however, {{street smart}} in the cartoon, able to organize and lead Girl Scouts like a gang leader. Amusingly, this changes the nature of her dynamic with Riley significantly.
* GenkiGirl / GirlyGirl: In the comics.
* GirlScoutsAreEvil: She runs her troop like a gang, selling Girl Scout cookies in an underhanded way. Later she helps Riley with his chocolate fundraiser in a similar manner. [[DoesThisRemindYouOfAnything The whole scheme spoofs the illegal drug trade]].
* InnocentBigot / InnocentlyInsensitive: [[http://hueyfreemanonlyspeaksthetruth.tumblr.com/image/40052056313 Extremely]] [[http://hueyfreemanonlyspeaksthetruth.tumblr.com/image/41157229724 so]]. At least in the comics; this part of her character is phased out in the show. It's implied to be because the only things she knows about black people come from TV and her bigoted father.
* LittleMissBadass: Her first instinct when getting taunted by [[TheMafia a man in a suspicious black limo]] is to chase him down with a baseball bat, for starters. She also [[GroinAttack knees a thug in the groin]].
* [[PrettyFlyForAWhiteGuy Pretty Fly For A White Girl]]: Parodied.
* TokenWhite
* {{Tomboy}}: In the show. Here, she's a wannabe gangster who plays basketball. As mentioned above she is a Girl Scout, albeit still acting like a gangster.
* TookALevelInJerkass: In the animated series, particularly in "The Fundraiser", where she harasses any competitors in the cookie or chocolate fundraisers.
* TroublingUnchildlikeBehavior: As seen in "The Fundraiser".

!!Otis "Thugnificent" Jenkins
-->'''Voiced by:''' Carl Jones

A not-very-bright gangsta rapper who moves into Woodcrest. Riley is his biggest fan. In Season 3, [[RichesToRags he becomes broke]] while his music career ends, so he then has to take a job as a UPS driver.
* [[AFatherToHisMen A Bro To His Men]]
* AscendedExtra: Albeit slightly; having only appeared in 3 episodes in Season 2, he appeared in 5 episodes for Season 3.
* AutoTune: Uses it in his album "Mo' Bitches, Mo' Problems." [[Music/KanyeWest Which fails spectacularly]] since he uses it in ''all'' his songs.
* BigDamnHeroes: In "The Fried Chicken Flu". Even after getting kicked out of Granddad's house, [[spoiler:Otis still managed to come to the rescue by using his van to ram the Neighborhood Militia bus off the road when they were chasing the Freeman and [=DuBois=] families]].
* CatchPhrase: "No homo."
* ChuckCunninghamSyndrome: He is absent from Season 4.
* ADayInTheLimelight: "Bitches to Rags".
* DrivesLikeCrazy
* EarlyBirdCameo: Kind of. That song "Booty Butt Cheeks" you hear throughout Season 1? He made that.
* FallenOnHardTimesJob: His attempt to sell crack. Later he finds work as a UPS van driver and postman.
* FeigningIntelligence: He unsuccessfully attempts to seem smarter when he supports Barack Obama during the 2008 election. His lack of actual political awareness results in him getting humiliated by Bill Maher on television.
* FireForgedFriends: Gets off to a rocky start with Granddad, but eventually they put aside their differences. This is especially apparent after [[spoiler:Otis gives up his "Thugnificent" persona]].
-->'''Thugnificent:''' Old man, I know I told you to go eat dicks in the past, but you alright with me.
* FunnyAfro
* GeniusDitz: Maybe. It turns out that Thugnificent has a college degree, although he chose a career as a "professional buffoon" in hip hop music. Later when he's no longer a rapper and he goes bankrupt, he tries applying for a white-collar job, but he's rejected for unprofessional behavior.
* HiddenDepths
** IMinoredInTropology: In the episode "The Story of Thugnificant," the title character congratulated Huey for his enjoyment of reading. Huey thought it wasn't a big deal, but what he didn't know was that Thugnificent has a bachelor's degree in communications, meaning he does understand the importance of education.
* ImportantHaircut: [[spoiler:After he sells his home]], he loses the "Mickey Mouse" afro.
* IncomingHam: The RunningGag of his arrival being heralded by a glass-shatteringly loud rendition of one of his own songs.
* IntergenerationalFriendship: With Riley [[spoiler:and later with Granddad]].
* JerkWithAHeartOfGold: He's an irresponsible idiot, but he's probably one of the nicest characters in the series.
* NiceJobBreakingItHero: Gets his buddy fired from his job, due to NoSuchThingAsHR.
** And again when he visits an Asian friend for help with his failing career and instantly got it just from simply asking. The thing though is that he brought Ed Wuncler III with him since he thought it was a drug deal. When Ed realized he wasn't getting any money out of it... yeah.
* NWordPrivileges
* [[RagsToRiches Rags to Bitches]]: He grew up in the shantytown of [[MeaningfulName Terra-Belle]], Georgia. But then he became a millionaire rapper.[[note]]"[[{{Pun}} Rags to Bitches]]" is the name of one of his albums.[[/note]]
** [[RichesToRags Bitches to Rags]]: He's a good showman but due to trying to preserve his image, [[RichInDollarsPoorInSense he's not the smartest when it comes to money]]. It ultimately derails his music career, though he adapts pretty well to relative poverty again.[[note]]"[[{{Pun}} Bitches to Rags]]" is the name of the episode in which this happens.[[/note]]

-->'''Voiced by:''' Music/SnoopDogg

A friend of Thugnificent, and a fellow rapper of the Lethal Interjection Crew.
''This section is a stub. Please help expand it.''

!!Derrick "Flonominal" Cornish
-->'''Voiced by:''' Music/BustaRhymes

Another friend of Thugnificent, also a fellow rapper of the Lethal Interjection Crew.
''This section is a stub. Please help expand it.''

-->'''Voiced by:''' [=DeRay=] Davis

Yet another friend of Thugnificent, and also counted as part of the Lethal Interjection Crew, although he's not a rapper.
* BigDamnHeroes: With Thugnificent in "Fried Chicken Flu".
* ButtMonkey: Usually the odd-man-out and the butt of jokes, as far as members of the Lethal Interjection Crew go.
* FallenOnHardTimesJob: Working at Wendy's.
* AFriendInNeed: He's the only one left in the Lethal Interjection Crew who sticks around when Thugnificent's money dries up.
* GoodIsDumb: While he's one of the kindest characters in the show, he's not particularly bright.
-->'''Leonard:''' You know what, when I tried [a buffalo wing], I thought to myself, "This tastes like chicken," [[LiteralMinded but the fact it's a buffalo]], I was like, naw, I don't want to say it out loud 'cause y'all gonna think I'm stupid. That's why I ain't get no chicken; I just got the buffalo.
* LovableCoward: He ''will not'' die for his chain.
* NiceGuy
** TokenGoodTeammate: When the Lethal Injection Crew were talking about what they were going to do if their careers fail, they all talk about becoming burglars and drug dealers. Only Leonard talked about getting a paying job, which he was immediately chewed out for.
* OddNameOut: The Lethal Interjection Crew consists of Thugnificent, Macktastic, Flonominal, [[MyFriendsAndZoidberg ...and Leonard]].
* TheRuntAtTheEnd
* {{Workaholic}}: He works so much when Thugnificent goes broke in the third season that you hardly see him out of his [[BadJobWorseUniform Wendy's uniform]].
** When he figures out that the mortgage on the mansion is $12,000 a month and his boss won't give him extra hours to cover it, he reasons that he'll try to work his job, do telemarketing, and sell art out of the drive-through window at the same time.

!!Betty von Heusen
-->'''Voiced by:''' Marion Ross

An elderly white woman who's in charge of the local neighborhood watch, along with a pro-gun interest group.
* CrazySurvivalist / RightWingMilitiaFanatic: She owns a lot of guns, and used to own an AngryGuardDog (until Lamilton killed the poor creature).
** After a series of burglaries in the neighborhood, she proposed ''militarizing'' the neighborhood watch.
** While she and some other old people were holding an armed pro-gun protest, they clashed with Rollo Goodlove's protest group and chased them away.
** During the so-called "fried chicken flu" outbreak, she and some other neighbors formed a "militia". They tried to rob emergency supplies from the Freemans (though oddly without using guns).
* [[GrumpyOldMan Grumpy Old Woman]] / ScrewPolitenessImASenior
* {{Jerkass}}: She's always a nasty curmudgeon when she appears.
* RacistGrandma: Rollo Goodlove plans to sue her after she called him a nigger.
* StrawCharacter: A caricature of NRA conservatives.

!!A Pimp Named Slickback
->''"Let us pray the Pimp's Prayer. Lord, please pray for the soul of this bitch and guide my pimp hand and make it strong, Lord, so that she might learn a ho's place. Amen."''
-->'''Voiced by:''' Katt Williams

[[ExactlyWhatItSaysOnTheTin A Pimp Named Slickback]]. He's a firm believer of a sexist outlook on life. He first appears as the boss of a prostitute named Cristal. He later offers Tom his own twisted advice about marriage problems.
* AccidentalMisnaming / InsistentTerminology: He hates it when people shorten his title to just "Slickback", insisting that one must say the whole name, including the "A Pimp Named" part.
* CatchPhrase: Whenever he needs to correct someone: "I'm ''A Pimp Named'' Slickback."
* CoolShades: Tinted purple to match his suit, even.
* InkSuitActor: He's based on Katt Williams' character "Money Mike" in the ''Film/{{Friday}}'' film series.
* {{Jerkass}}: He IS a pimp after all.
* LeanAndMean
* OnlyInItForTheMoney: Everything he does is motivated by money (and sex of course).
* OnlyKnownByTheirNickname
* PimpDuds / PurpleIsPowerful: Wears a purple suit, like any cliched pimp would.
* PoliticallyIncorrectVillain: He's very misogynistic. But would you expect any better from a pimp?
* SmokingIsCool: He smokes. He's cool.
* WouldHitAGirl: If only "Rarely Considers ''Not'' Hitting A Girl" were a trope, he'd be that too. He regards this as normal and something every man should be doing as often as is necessary, putting him at odds with Robert and Tom who both WouldntHitAGirl. His reaction when Tom [=DuBois=] refuses to consider hitting his wife CrossesTheLineTwice:
--> '''A Pimp Named Slickback:''' It's okay, Tom. We all got phobias.

!!Butch Magnus Milosovic
-->'''Voiced by:''' Daryl Sabara

A bully who antagonizes Riley in "Shinin'", by stealing a chain necklace from him. Also cameos in "The Red Ball" (as part of the Woodcrest kickball team), and "A Date With The Health Inspector" (as part of a group of other suspended students touring the prison).
* TheBully: Obviously. His modus operandi seems to be beating down and robbing people blind.
** BarbaricBully
** RedHeadedBully
* {{Delinquent}}
* EnfanteTerrible: He's built up a well-earned reputation as this around town.
* FatBastard
* {{Jerkass}}
* MightyGlacier
* MegatonPunch: Hence his nickname, "One-Punch Butch."
* NamesToRunAwayFromReallyFast
* StoutStrength: Butch can easily overpower adults; as demonstrated when he knocks down a [[HollywoodNuns Catholic school nun]], a {{drill sergeant| nasty}}, and Flonominal.
* TroublingUnchildlikeBehavior

!!Rev. Rollo Goodlove
-->'''Voiced by:''' Cee-Lo Green

A black liberal activist who seems to be more interested in money and publicity, instead of actually advancing any causes. Appears in "The S-Word", "The Hunger Strike", and "The New Black".
* AngryBlackMan: Though he seems to be exaggerating quite a bit of that anger on purpose.
* AttentionWhore: Oh yeah.
* {{Expy}}: An unflattering lampooning of Al Sharpton.
* NWordPrivileges: "The S-Word" is about Rollo helping out Robert and Riley in their attempt to sue the school district, because Riley's teacher Mr. Petto had said "nigga"; even though Riley, Robert, and Rollo all use that word casually; and Petto was simply copying Riley's words without malice, and tried to apologize afterwards.
* StrawCharacter: He's depicted as a straw liberal who launches a lot of bogus protests for the sake of publicity.
** StrawHypocrite: Besides the problem with his NWordPrivileges as stated above, Goodlove once helped out with Huey's protest against BET, only to end it by getting his own sitcom on that same channel.
* WhereDaWhiteWomenAt: He's attracted to Ann Coulter (who in this universe, only pretends to be a right-wing firebrand).

!!Frederick "Gangstalicious"
-->'''Voiced by:''' Mos Def

Riley's other favorite rapper, who also happens to be a closet gay man.
* ArchEnemy: Has a feud with rival rapper Eat Dirt that turned violent.
* ArmoredClosetGay: Gangstalicious keeps denying that he's homosexual, despite increasingly obvious hints that he is.
* BrokenPedestal: Subverted, as Riley says that he's telling "their stories."
* ExpectingSomeoneTaller: His videos make him out to be a lot bigger than he actually is.
-->'''Riley''': Damn, nigga, you short.
* FakeUltimateHero: To Riley, though he gets over it pretty quickly as despite his flaws, Gangstalicious is a great performer and very nice to his fans.
* {{Gayngster}}: Gangstalicious was once in love with a street thug, but their break-up turned violent. Fortunately, his ex-boyfriend was very bad at trying to murder him.
* JerkassFacade: His gangsta persona is a complete act; he's actually a mild-mannered gay man from the Midwest, not at all cut out for the dangerous hardcore gangsta rap scene.
* OnlyAFleshWound: Was shot twice on stage, one of them in his right shoulder, and laid there bleeding out for 45 minutes before anyone thought to call an ambulance. [[UnexplainedRecovery He got better]].
* StraightGay: He tries to put on a tough guy gangster image, at least at first...
** CampGay: But in his second appearance, he starts to display some homosexual stereotypes. For example his homoerotic "Homies Over Hoes" song and music video, and he also promotes a fashion line of very feminine-looking clothing, which his fans are completely oblivious to.
* YouAreTheNewTrend: After his extremely successful "Homies Over Hoes" single drops, a lot of his fans start buying from his ridiculous new fashion line.

!!The White Shadow
-->'''Voiced by:''' John C. [=McGinley=]

Huey's nickname for a federal agent who seems to be stalking him. Is he real, or imaginary? He seems to know everything about Huey. He appears in "The Real" and "It's Going Down".
* FriendlyEnemy: "Just because I tape your phone conversations and monitor your emails doesn't mean we can't be friends."
* MaybeMagicMaybeMundane: It hasn't been revealed just who or what the White Shadow actually is. Only [[ConspiracyTheorist Huey]] has seen and heard him, making him wonder if the Shadow is just a paranoid hallucination.
* TheMenInBlack: The White Shadow's job is to monitor Huey but has nothing to do with covering up the paranormal, but he certainly has the appearance.
* TheSchizophreniaConspiracy: In "The Real", Huey concludes that he's either crazy, or that the government is trying to make him think he's crazy.
* SpiritAdvisor: In "It's Goin' Down", the White Shadow warned him of the imminent invasion of his home by actual federal agents, something that Huey had no idea was going to happen. This could hint that he's a real man and not an illusion.

!!Bushido Brown
-->'''Voiced by:''' Cedric Yarbrough, later Creator/MichaelJaiWhite

A legendary swordsman, martial artist, and professional bodyguard. He was hired by Oprah Winfrey, and later by Robert Freeman.
* AfroAsskicker: He looks like a 1970s {{Blaxploitation}} movie protagonist.
* ArrogantKungFuGuy: ''Very'' arrogant.
--> '''Robert Freeman:''' Did you just tell me to wipe your ass?
* AwesomeMcCoolname
* {{Badass}} He can back up his arrogance.
** MemeticBadass: InUniverse, his reputation is greatly exaggerated. He's still quite possibly the best fighter on the show. He's also one of two notable characters in the whole show to have fought in the Kumite ([-[[RunningGag HU-CHYA!]]-]).
* {{Expy}}: Of 1970s actor / martial artist Jim Kelly.
* InsistentTerminology: Grand''master'' Bushido Brown.
* {{Jerkass}}: In addition to being an egotist, he charges Robert ridiculously high fees, and forces him to buy things for him.
* NominalHero: He won't help anyone out of generosity.
* OccidentalOtaku: Aside from the obvious, his demands in return for helping the Freemans in Season 3 include large amounts of sushi and one of those "Japanese butt-cleaning toilets".
* OnlyInItForTheMoney: He's a professional bodyguard who demands a high paycheck if you need to hire him.
* [[spoiler:OffWithHisHead: He loses his head when fighting the Hateocracy.]]

-->'''Voiced by:''' Marlin Hill

The current President of the United States. His election is the focus of "It's A Black President, Huey Freeman", and he also cameos in "The Fried Chicken Flu" and "It's Goin' Down" (voice only).
* EmergencyPresidentialAddress: Parodied in "The Fried Chicken Flu", where all President Obama was talking about during the crisis is how he's perfectly safe in the White House bunker, not bothering to hide that things won't be so okay for the common people.
* HypeBacklash: In-universe example: In "It's a Black President, Huey Freeman", liberal Democrats are enthusiastic about the first African-American President, while conservative Republicans such as Uncle Ruckus are unhappy about him, and Huey is totally apathetic about the whole election.
** Among the people shown supporting Obama (Robert, Riley, Tom, Sarah, Thugnificent, etc.), they all seem disappointed for various reasons (except for Sarah, who is pleased by Obama's charm alone).
* ObstructiveBureaucrat: He calls Jack Flowers to tell him that he can't arrest Ed Wuncler I.
* TakeThat: The show has a decidedly negative view of Barack Obama, depicting his campaign as being nothing more than one big hype machine.
** Also anyone who read the comics would know that the creator wasn't fond of George Bush Jr. before him.

[[folder:Minor Characters]]
!!Psycho Star Wars Guy
A ''Franchise/StarWars'' fanatic who only appears in some early comic strips.
* AdaptedOut: Doesn't appear in the TV series. He wasn't even a regular for most of the comics' run.
* BasementDweller: Lives with his parents without going to college or getting a job, is somehow entitled to an allowance, and he just spends his days camping outside of movie theaters in anticipation of ''Film/ThePhantomMenace'' and ''Film/AttackOfTheClones''.
* ChuckCunninghamSyndrome: He was unused after an appearance at a movie theater, waiting in line for ''Film/AttackOfTheClones''.
* DespairEventHorizon: Goes temporarily insane after the release of ''Film/ThePhantomMenace''. Huey has to snap him out of it.
* ExactlyWhatItSaysOnTheTin: He's a ''Franchise/StarWars'' enthusiast who dresses like Obi-Wan 24/7, and doesn't seem to have much of a life outside of ''Star Wars''.
* {{Geek}} / {{Nerd}}: He even admits that the stereotypical demographic of ''Star Wars'' fans are white males who have no lives, [[SelfDeprecation such as himself]].
* LiteralAssKicking: Delivers one to Creator/GeorgeLucas at Huey's (joking) suggestion, as revenge for ''Film/ThePhantomMenace''.
--> [[BondOneLiner "May the force of my foot in your behind]] [[AwesomeMoments/{{TheBoondocks}} be with you, always]]."
* LooksLikeJesus: Helped by having long hair, a beard, and walking around in a Jedi robe.
* SeriousBusiness: ''Star Wars''. Sometimes Huey sees eye-to-eye with him on this; sometimes not quite so much.

-->'''Voiced by:''' Tiffany Thomas

A prostitute whom Robert dated in "Guess Hoe's Coming To Dinner". She works for A Pimp Named Slickback.
* AmbiguouslyBrown: She has blonde hair and light skin, but speaks with a ghetto accent. Riley calls her a "fake-ass Music/MariahCarey".
* GoldDigger: Dates Robert because he's obviously above her social class. A song called "Gold Digger" even plays in the background at one point.
* HookerWithAHeartOfGold: Maybe.
* StatusQuoIsGod: [[spoiler:At first it seems that she takes Robert's advice to start a clean and honest life by getting an education and a real job, but instead she just runs back to Slickback, not knowing any different lifestyle.]]
* {{Streetwalker}}

!![[UsefulNotes/CivilRightsMovement Martin Luther King Jr.]]
-->'''Voiced by:''' Creator/KevinMichaelRichardson

The iconic leader of the Civil Rights Movement. Appears in a what-if scenario in which he survived getting shot in 1968. He loses his mainstream popularity after suggesting non-violence in a post-9/11 world. He is also repulsed by modern African-American society.
* AlternateHistory: Instead of getting assassinated in 1968, he survived but remained comatose for about 32 years, before waking up and dying of old age several years later.
** AllJustADream: Although the episode he appeared in is hinted to just be Huey's dream or imagination.
* FishOutOfTemporalWater: Obviously, he still has yet to get used to a different world over three (nearly four) decades later.
* TheReasonYouSuckSpeech: A disillusioned King gives one to [[StopBeingStereotypical a crowd of stereotypical African-Americans]], calling them a bunch of "ignorant [[NWordPrivileges niggers]]" for wasting their lives by committing astounding acts of stupidity.
* ScrewThisImOuttaHere: Having become too cynical, he moves away to Vancouver, Canada where he spends his last years.

!!Art Teacher
-->'''Voiced by:''' Creator/RobPaulsen

A painter who gives Riley some art lessons after he's caught spraying graffiti. Ironically, he helps Riley improve his graffiti skills by adding a more artistically talented bent to it. It eventually culminates with Riley painting [[spoiler:a mural of his (grand)parents' wedding, which moves Granddad to tears]].
* [[spoiler:AffablyEvil: He's a criminal who jumps from being an accomplice to vandalism, to trying to shoot at the police.]]
* {{Expy}}: Of [[http://en.wikipedia.org/wiki/Bob_Ross Bob Ross]].
* FunnyAfro: He's a white guy with a big blonde afro.
* HypocriticalHumor: He tells Riley that he doesn't like violence. [[spoiler:Apparently shooting at the police doesn't count.]]
* ShellShockedVeteran: According to rumor, he's a Gulf War veteran who had a nervous breakdown.

!!Moe Jackson
-->'''Voiced by:''' Mike Epps

An old friend of Robert whom he knew from World War II. Apparently not a good friend, as they split due to Moe's jerkiness and a dispute over a woman. Robert attends his funeral in Chicago.
* FakeUltimateHero: He tried to take credit for some of Robert's wartime medals and achievements.
* TheFriendNobodyLikes: It turns out that everyone who knew Moe had this relationship with him. Everyone is left wondering what they actually liked about him.
* {{Jerkass}}: His goofing around nearly got Robert killed in combat, loved to mess around with everyone in general, and [[spoiler:in his will Moe promised something nice for Robert... which was just a jar of foam peanuts]].
* PosthumousCharacter: Robert remembers him through flashbacks and a video will.
* ThePrankster / {{Troll}}: Not even his impending death would end his capacity for annoying jokes and pranks.

-->'''Voiced by:''' Aisha Tyler

Luna is the antagonist of "Attack of the Killer Kung-Fu Wolf Bitch". She was briefly Robert's girlfriend, but she turned out to be a deadly martial artist who was emotionally unstable. She doesn't take his rejection well...
* AffablyEvil: Luna just wants to date Robert, until he dumps her due to his fear of her abilities. And then she has a VillainousBreakdown.
* AndShowItToYou: She ripped out somebody's heart back in the Kumite ([-[[RunningGag WA-TA!]]-]), all completed with this line:
--> [[MortalKombat '''FINISH HIM!''']]
* AxCrazy: ''Oh yes''.
* {{Badass}}: She beats the utter shit out of Huey.
* BerserkButton: Any time she thinks that a man has wronged her somehow, whether it's physical or emotional abuse, or just being lied to.
* BloodKnight: She proudly recalls the time that she fought in the Kumite contest and killed a man with her bare hands, which disturbs the Freemans.
* BrokenBird: Her past relationships has reduced her to this. Her friend Nichole does nothing to help.
* CuteAndPsycho: Despite her sexy appearance and overall nice demeanor, she's pretty unstable.
* CuteBruiser: Definitely. She once ripped a man's heart out with her bare hands.
* DarkActionGirl: See CuteBruiser
* DarkAndTroubledPast: "Troubled" would be an understatement for this girl; aside from being RaisedByWolves, Luna has suffered every type of abuse in every relationship she's been in. It doesn't help that she grew up in a broken home with an abusive father.
* DisproportionateRetribution: Like her mother, Luna was severely abused over the slightest things, whether the cooking was cold or the laundry was done wrong.
** Her friend Nicole doesn't help, either; she suggested that Luna should just outright ''kill'' Granddad just for cutting their weekend short.
--> '''Nicole:''' Now, remember, this is not your fault. This man took your weekend from you. Two days you'll never get back! You gotta kill him.
* DomesticAbuse: Her mother suffered from it at the hands of her [[AbusiveParents father]], and she would suffer the same from other boyfriends (before she met Granddad). Her dad and one boyfriend would go berserk over ''fried chicken'':
--> '''BITCH, THIS CHICKEN IS COLD!''' ''(slap)''
* FemmeFatale
* [[spoiler:InterruptedSuicide]]: Only most likely because Granddad and Tom [[spoiler:were in the same room and tied up when Luna contemplated whether she should blow herself up with a grenade]].
** [[spoiler:DrivenToSuicide:]] [[SarcasmMode Thanks a lot, Nicole]].
* LargeHam: "If I could just find a man to love me-he-he-he-he *gasp* eh-he-he-he-he *gasp* eh-he- *beat* [[OverlyLongGag -eee]]."
* PoisonousFriend: She hangs on Nicole's every word, even if she tells her to kill Graddad, [[spoiler:or herself]].
* MeaningfulName: Luna is a lunatic. It also invokes the Moon, and her love of wolves.
* MediumAware: When she arrives at the Freeman's home, her Myspace page appears beside her and she looks over at it.
* RaisedByWolves: She also owns ''fifteen'' of them.
* SheFu: She beats the living shit out of Huey, chokes out Granddad, and tosses Tom across the room by the neck with her legs.
** WaifFu: Luna is also much stronger than she looks, as she is seen a flashback beating the crap of a guy three times her size in the Kumite ([-[[RunningGag HIYAA!]]-]) flashback and ''rips his heart right out of his chest''. She also laments wiping the floor with Huey by ''punching a hole in the wall''.
* SkilledButNaive: A literal example; she's practically a trained killer, but easily fell for Granddad's UsefulNotes/FidelCastro lie.
* StepfordSmiler: First she's a pretty bombshell, then a dangerous psycho, until finally she's just a sad girl.
* ToxicFriendInfluence: Her friend Nicole is the epitome of this trope.
* TragicVillain: Her past relationships ''sucked''.
* UnusualEuphemism: Her "friendly sparring match" with Huey [[CurbStompBattle wasn't so friendly...]][[spoiler: for Huey, that is]].
* WhamLine: "I thought you were going to say that I was crazy and you didn't want to see me again ''like the others''."
* {{A Wolf|In Sheeps Clothing}}[=-=]BitchInSheepsClothing: Robert certainly wasn't expecting a woman who turned out to be as insane as she was beautiful.
* WomanScorned: She rose hell when she found out Granddad lied to her about attending UsefulNotes/FidelCastro's birthday party.
* {{Yandere}}: And ''how''.

!!Jericho Freeman
-->'''Voiced by:''' Cedric the Entertainer

A relative of Robert Freeman. Jericho and his branch of the family fled from New Orleans after Hurricane Katrina, only to move into Robert's house and shamelessly mooch off of him. He first appeared unnamed in one late comic arc, which was adapted into "Invasion of The Katrinians".
* ConMan: After mooching off of Granddad for a few months, he pretends that FEMA denied his compensation request so that he won't have to pay him or anyone back.
* FatBastard / FatSlob
* ForgotToPayTheBill: Really, Robert neglected to pay the utilities and phone bills in the hopes it would send the New Orleans Freemans packing.
* {{Jerkass}}
* KarmaHoudini: Gets no comeuppance for draining Robert's money.
* LazyBum: He spends all of his time waiting for FEMA to pay for his life and family instead of going out and actually getting a real job.
* TheLoad
* LowerClassLout: He and his family are rather unflattering depictions of poor black people: lazy, uneducated, and having too many kids. Even ''Riley'' has a low opinion of them.
* RaginCajun: Lived in New Orleans when the hurricane hit.
* TheTramp
* UngratefulBastard: Doesn't seem to care one bit that Granddad let him and his family live in their house or gave him money to help them out.

!!Deborah Leevil
-->'''Voiced by:''' Debra Wilson

The evil CEO of the Creator/{{BET}} network, who plans to destroy black people.
* BadBoss: She murders two members of her board of directors for pushing her BerserkButton.
* BerserkButton: Which is to question her evil plans or be ignorant of them.
* BoomerangBigot: Deborah and her coworkers hate black people, so they use Creator/{{BET}} to keep them dumbed down.
* CardCarryingVillain: She's only interested in green-lighting TV shows she deems to be ''evil'' enough.
* CorruptCorporateExecutive: She runs the BET network like a supervillain organization.
* EvilIsHammy / LaughablyEvil: She's a horribly sadistic woman who actively tries to destroy the health of her fellow black people, but she is so erratic in her actions that it's hard not to laugh at her.
* EvilLaugh: She's got quite a sadistic laugh at that.
* {{Expy}}: A parody of real CEO [[http://en.wikipedia.org/wiki/Debra_L._Lee Debra L. Lee]] and [[Film/AustinPowers Dr. Evil]].
* InsistentTerminology: She says that BET doesn't stand for Black Entertainment Television, but Black ''Evil'' Television. Not knowing this costed one of her show producers their life.
* {{Jerkass}}: You don't say?
* KarmaHoudini: She is never seen again after killing one of the board members, and threatening to do the same to Wedgie if he doesn't give her an evil television show. [[CorruptCorporateExecutive Given her career]], [[ScrewTheRulesIHaveMoney it's unlikely she was ever punished]].
* {{Sadist}}: Especially shown when she murders one of her board members, laughing while the blood splashed over her face.

!!Wedgie Rudlin
-->'''Voiced by:''' Donald Faison

The President of BET. He produces a reality show starring Uncle Ruckus.
* BoomerangBigot: Why else would he give Ruckus a spotlight on TV?
* CorruptCorporateExecutive: Not only is his boss one of these, he tries to torture a geneticist into "correcting" a DNA test, in order to trick Ruckus into thinking he's white again (Ruckus almost killed himself over his black heritage, which would've ended the show prematurely).
* TheDragon: To Deborah Leevil. Though it seems that he continues working for [[BadBoss her]] under fear for his own life.
* {{Expy}}: He's a parody of [[http://en.wikipedia.org/wiki/Reginald_Hudlin Reginald Hudlin]], who was (very briefly) an executive producer of ''The Boondocks'', before he became the president of BET.
* {{Jerkass}}: He fires someone for a trivial reason, and takes away his business lunch.
* MotorMouth: He rambles on and on at meetings.
* ProfessionalButtKisser / YesMan
* TheWhitestBlackGuy: He boasts about having a business degree from the [[WhiteAngloSaxonProtestant WASP]] [[IvyLeague Harvard University]] instead of "one of those [[http://en.wikipedia.org/wiki/Historically_black_colleges_and_universities historically black colleges]]".

!!Mr. Long-Dou
-->'''Voiced by:''' Sab Shimono

A wealthy businessman from Wushung, China. He tries to settle Ed Wuncler I's debt to him by gambling with the outcome of a kickball game.
* AffablyEvil: He's very polite and well-mannered.
** FriendlyEnemy / WorthyOpponent: He respects Wuncler as a worthy rival.
* CorruptCorporateExecutive: He's a gambling addict who bets the financial fate of a city over a sports match. He also bribes the referee to allow his team to cheat.

!!Ming Long-Dou
-->'''Voiced by:''' Tiffany Espensen

Mr. Long-Dou's granddaughter, who has been trained as an expert kickball player. Ming was Huey's rival and opponent in a kickball game.
* AntiVillain: Subverted. She lies about being forced to play kickball so that Huey would go too easy on her.
* LittleMissBadass: Ming is not TheNatural like Huey, but her lesser talent has been painstakingly trained to do one thing: win at kickball.
* NotSoDifferent: Invoked. Ming manages to psych Huey out for a time by exploiting this trope.
* SeriousBusiness: Her entire life, her function, is kickball.
* TykeBomb: Not to bring up kickball again, but say it with us: kickball.
* WorthyOpponent: Huey comes to realize that he's finally up against somebody as furious, ruthless, and determined as he is.

!!Jimmy Rebel
-->'''Voiced by:''' Nick Jameson

A white nationalist country singer known for almost exclusively recording anti-black music. Much to his surprise ([[DramaticIrony but not ours]]), his biggest fan is [[BoomerangBigot a black man named Uncle Ruckus]]. The two become close friends.
* AesopAmnesia: In the end, Jimmy states that he's not as racist as he used to be, and wants to sing about other subjects besides hating black people. But then Jimmy and Ruckus team up to write an anti-Mexican song.
* [[AffablyEvil Affably Bigoted]]: He may be extremely racist, although he has an otherwise genial personality.
* DeepSouth: Hails from a city there called Spokenhoke, which he calls "the Jewel of the South". It's also the location of the headquarters of his record label, Racist Records.
* [[EvenEvilHasStandards Even Racists Have Standards]]: He makes an exception to his hatred of black people for his kindred-spirited friend, Uncle Ruckus. This puts Jimmy at odds with his own audience though.
* {{Expy}}: He's based on a real racist country singer known as Johnny Rebel.

!!The Hateocracy
-->'''Voiced by:''' Aries Spears (Rufus Crabmiser), Carl Jones (George Pisstofferson), Bebe Drake (Esmeralda Gripenasty)

Stinkmeaner's old crew of equally nasty senior citizens, who roll into Woodcrest looking to kill the Freemans. They consist of '''Rufus Crabmiser''', '''George Pisstofferson''', and '''Esmeralda Gripenasty'''.
* AvengingTheVillain: Subverted, they weren't really moved by Stinkmeaner's death. The thin veneer of "revenge" was just an excuse to attack the Freemans for the fun of it.
* {{Badass}}es: The three old codgers whoop heaps of ass and [[spoiler:kill Bushido Brown]]. The only thing that can defeat them? [[spoiler:Jail.]]
** BadassBeard: Crabmiser has an old sailor's beard.
** BadassCrew: All three of them of course.
** BadassGrandpa / NeverMessWithGranny: Despite being really old, they seem to be far stronger and more agile than most people much younger than them.
* BaldWoman: Esmeralda wears a wig.
* {{Card Carrying Villain}}s: What do you expect when they name their group "The Hateocracy"?
* CurbStompBattle: Their fights with Ruckus, Huey, and Riley (especially Ruckus, who was hospitalized). Robert was lucky because of a convenient bucket of live crabs thrown at Crabmeiser's face.
* EvilOldFolks: A whole trio of them!
* {{Exp|y}}ies: George Pistofferson, Rufus Crabmiser, and Esmeralda Gripenasty are based on [[Series/GoodTimes JJ Evans]], [[Series/SanfordAndSon Fred Sanford, and Aunt Esther]] respectively.
* ForTheEvulz: As they explain, they weren't looking to avenge Stinkmeaner, they just wanted to fuck something up.
* {{Jerkass}}es: What do you expect when these three assholes are the closest thing that ''Stinkmeaner'' has ever had to being a circle of friends? Even then they admit that they don't actually like each other, due to their ambivalence towards Stinkmeaner's death.
* ImprobableWeaponUser: Crabmiser uses a weaponized lobster cage with blades on the side.
* {{Sadist}}s / {{Sociopath}}s
* WalkingTheEarth: After their dickish behavior got them kicked out of the nursing home they met in, they wandered the world for ten years together before splitting up.
* WouldHurtAChild: They have no qualms about trying to kill children. George and Esmeralda even attacked Huey and Riley at their school.
* VillainsOutShopping: Crabmiser enjoys crab fishing in his spare time, though when he's introduced doing this, he's also trying to kill Robert.
* VitriolicBestBuds: Though in a twisted way that only complete sociopaths such as themselves could understand. All four of them were misanthropes who hated everyone in the world, but hated each other slightly less. The surviving three weren't actually interested in avenging their fallen acquaintance Stinkmeaner, they just needed an excuse to harass the Freemans.

!!Lamilton Taeshawn
-->'''Voiced by:''' Bobb'e J. Thompson

A sociopathic delinquent. Riley makes the mistake of hanging out with him.
* AbusiveParents: Apparently he was horribly abused by his mom and dad. Inverted with his grandma, who is horribly abused by ''Lamilton'' himself!
* TheBully: Even worse than Butch Magnus.
* CardCarryingVillain: He enjoys being "a bad kid". Also see ForTheEvulz.
* CatchPhrase: "[I like to do] bad things."
* CreepyChild / EnfanteTerrible: His former school counselor actually suggested he's TheAntiChrist.
* {{Delinquent}}: His idea of having a fun time is to commit all kinds of petty crimes, from dropping objects on passing cars, to shooting a chained dog.
* DisproportionateRetribution: Beat up his grandma because she didn't get him fried chicken.
* DrivesLikeCrazy: Well, what do you expect? He's only eight.
* {{Expy}}: A ''very'' transparent parody of [[http://www.youtube.com/watch?v=qcqOgnQyXp4 Latarian Milton, a seven-year-old kid who also took his grandmother's SUV for a joyride]], down to even having a {{catch phrase}} very similar to one of Latarian's more troubling quotes ("It's fun to do bad things").
** He's also one of [[Film/TheGoodSon Henry Evans]]. Both are {{False Friend}}s of the protagonist, both are {{Sadist}}s who do evil things for fun, and both kill dogs. Also, both end up falling from a high place (a school building for Lamilton, a cliff for Henry), though Lamilton survived due to his fat protecting him from the fall, while Henry is confirmed to be dead.
* FalseFriend: Lamilton acquaints himself with Riley. Eventually though Riley, a boy who usually doesn't learn from his mistakes, realizes there's something very wrong with his "friend" and tries to leave when Lamilton goes too far.
* FatBastard: Robert even calls him a "fat fucker".
* ForTheEvulz: "I like to do bad things... because they're fun."
* FreudianExcuse: His grandmother states that he came from a very {{abusive| parents}} and {{dysfunctional family}}.
* HorribleJudgeOfCharacter: Lamilton's grandmother keeps making excuses for his misbehavior, insisting that he's really a good kid deep down, and thinks he can change his ways.
* {{Jerkass}}: Oh yes, and he can barely hide it. His facade of friendship with Riley is quite shallow.
* KnightOfCerebus: His scenes were among the rare moments not {{played for laughs}}.
* LackOfEmpathy: He makes it clear that he doesn't care about other people.
* MadeOfIron: Fell off the roof of the J. Edgar Elementary School, and tried to drive off the counselor hounding him as he limped back to his grandma's house.
* OminousLatinChanting: "LAM-IL-TON! TE-SHAWN!"
* {{Sadist}}: While he doesn't even smile about it, one can tell that he enjoys inflicting torment.
* SmokingIsCool: He certainly thinks so.
* ShootTheDog: ''Literally'', as he guns down Betty von Heusen's guard dog, claiming "self-defense" even though the dog was still chained when he tried intruding onto von Heusen's yard.
* TheSociopath: His purely evil nature drove his therapist insane.
* TheStoic: Done to very creepy effect, with Lamilton barely making any facial expressions or speaking differently from his constant monotone. It seems he only knows a few emotions: sadism, anger, and fear (you too would scream if you fell from a building and got injured).
* StoutStrength: At least enough to deliver an intense beating to his grandmother. Though he's not as strong as Butch Magnus, as Riley could hold his own against Lamilton.
* StupidEvil / TooDumbToLive: Lamilton even claims not to care much about himself. His reckless crimes threaten not only other people but himself as well; he smokes even though it poisons his lungs, almost got himself killed when trying to joyride in his grandma's car, and he even wanted to burglarize the home of a heavily armed old woman.
* TroublingUnchildlikeBehavior: The most stand-out example of the series so far.

!!Dr. Doomis
-->'''Voiced by:''' Creator/TomKane

Lamilton's psychiatrist. After studying his anti-social behavior, Doomis became obsessed with stopping Lamilton before he ends up killing someone.
* CriticalPsychoanalysisFailure: Lamilton's sociopathy and utter lack of humanity drove Doomis to madness.
* {{Expy}}: Of Dr. Loomis from ''Franchise/{{Halloween}}''.
* ProperlyParanoid: While he may be too obsessive about Lamilton and his actions, he is correct that the kid is quite evil.
* StalkerWithoutACrush: He closely follows and monitors Lamilton, to the point that his grandmother filed a restraining order against him.
* WellIntentionedExtremist: Doomis believes that Lamilton shouldn't walk free, and should either be locked away forever or die.

!!Alistair Rigby
-->'''Voiced by:''' Creator/GregEllis

The boss of the UK-based World's Ultimate Chocolate company, which produces chocolate bars for school fundraisers - and also happens to be a front for organized crime. He doesn't react well to Riley and his friends starting their own chocolate business.
* [[spoiler:BoomHeadshot / KilledMidSentence: Courtesy of TheMafia, who also wanted to conquer the chocolate trafficking industry.]]
* CorruptCorporateExecutive: He runs his corporation as a crime syndicate.
* EvilBrit / LondonGangster: Riley even mocks everything British in front of him.
* WouldHurtAChild: Has no problem with using mobster-style intimidation against kids. He even has guns aimed at Riley and Cindy.

!!Winston Jerome
-->'''Voiced by:''' Affion Crockett

A gay black playwright/screenwriter. In "Pause", he recruits Granddad to act in one of his productions, but he is oblivious to Winston's plan to have sex with him.
* AllGaysLoveTheater: And that's just one item of his checklist of gay stereotypes.
* ArmoredClosetGay: Winston keeps insisting that he's a heterosexual Christian man, until the climax when he admits that he really is just trying to find men to sleep with.
* CampGay: No man can be more effeminate than him.
* CreepyCrossdresser: He's known for playing a Madea-like character.
* [[{{Cult}} Cult Leader]]: His quasi-Christian theater group requires its members to live in a compound, and sever any ties to their old lives.
* {{Expy}}: A spoof of Creator/TylerPerry.
* UncleTomfoolery: His plays and movies make use of a lot of black stereotype humor.

!!The Booty Warrior
->''"I like ya, and I want'cha. Now we can do this the easy way or we can do this the hard way, the choice is yours."''
-->'''Voiced by:''' Carl Jones

When Tom and Ruckus take Huey, Riley, Butch, and four other boys on a visit to jail to scare them straight, they meet an inmate who is obsessed with anal rape. In other words, the personification of Tom's worst nightmares!
* BlackComedyRape: His sexual assault on Chris Hansen is PlayedForLaughs.
** DoubleStandardRapeMaleOnMale
* CatchPhrase: "I like ya, and I want'cha. Now we can do this the easy way or we can do this the hard way, the choice is yours."
* DepravedHomosexual: Was sent to prison specifically because he anally raped Chris Hansen in the middle of shooting ''Series/ToCatchAPredator''.
** He describes "booty" as the most important thing in prison life, more than food or water.
** When his fellow inmates ask him if he had an escape plan, he states that all he wanted was to get to rape Tom.
* EvenEvilHasStandards: He doesn't rape children, it was just a ruse to get Chris Hansen.
* {{Expy}}: He's based on real life inmate Fleece Johnson, right down to his signature catchphrase.
* GoneHorriblyRight: While he seemed to have started the prison riot on purpose, it turns out, he simply wanted to anally rape Tom.
* PrisonRape: He's part of a group of several prisoners who are also obsessed with raping other prisoners (although they also demand to have "([[WhereDaWhiteWomenAt white]]) [[DepravedBisexual bitches]]" imported into the prison).
* RapeIsASpecialKindOfEvil: He and some fellow prisoners ironically warn the boys about risking a lifetime of getting raped behind bars.
* ScaryBlackMan: He's not as huge as the "Health Inspector" of Tom's nightmares, but still just as scary.
* StalkerWithACrush: He pursues specific men in mind before he tries to rape them. He appeared on ''To Catch A Predator'' just so he could get to Chris Hansen, despite TV cameramen and police officers waiting for him. And he later starts a prison riot, just so he could chase down Tom through the halls of the jail.

-->'''Voiced by:''' Gerald Johnson

A gardener and landscaper who claims to be the illegitimate son of Robert Freeman.
* ButtMonkey: Not surprisingly, he gets into quite a bit of mishaps when he moves in with the Freemans.
* LukeYouAreMyFather: He claims to be the offspring of Robert and one of his girlfriends born circa 1980. [[spoiler:According to a DNA test however, Lando is in fact NOT the son of Robert Freeman.]]
** LukeIAmYourFather: [[spoiler:Ironically Billy Dee Williams (the actor who played Lando Calrissian) claims to actually be Lando's father.]]
* MeaningfulName: Lando sharing a name with ''Franchise/StarWars'' character Lando Calrissian is noted, while Lando mentions that around the time he was conceived, his mother and father watched ''TheEmpireStrikesBack''. [[spoiler:In fact, the actor who played Lando Calrissian is his real father.]]
* NiceGuy: Overall, he's a very friendly man. However, during his journey to discover his father, he's brought into conflict with some other people (especially Uncle Ruckus and TV host Steve Wilkos).

!!Ebony Brown
-->'''Voiced by:''' Creator/GinaTorres

Robert's GirlOfTheWeek in "The Lovely Ebony Brown". Unlike Robert's previous girlfriends, Ebony is a very pleasant woman and not bat-shit crazy at all. In the end though, Robert's paranoid insecurities lead them to splitting up anyways.
* HundredPercentAdorationRating: She's so charming that all of the main characters seem to like her. Not even the cynical Huey and Riley (who've met all of Robert's crazy girlfriends), or even the black-hating Ruckus [[spoiler:(who develops his own crush on her)]] can find any genuine faults about Ms. Brown.
* TheAce: Bordering on ParodySue. Ebony Brown is athletic, beautiful, kind, smart, and successful. Essentially, a perfect woman.
* MetaGirl: She {{lampshades}} the show in a LeaningOnTheFourthWall kind of way. She finds Robert Freeman's life stories about all his crazy misadventures and wacky people to be very entertaining. She even asks if she can be a "main character" in his life.
* NiceGirl: She's probably the most good-natured person that Robert has ever met. Despite this, Robert's paranoia that Ebony doesn't find him attractive enough derails their relationship.

!!Mister Ruckus
-->'''Voiced by:''' Don Curry

The father of Uncle Ruckus. Uncle (his actual name) hates his dad with a passion (and with good reason).
* AbusiveParents: Extremely so. He had an explosive temper and beat around a young Uncle Ruckus for little or no reason. He eventually throws Uncle out of the house.
* CatchPhrase: "Nigga, did I just catch you [doing something]?!" ''(slap)''
* EvilOldFolks: Old age has not watered down his asshole behavior. However, his own mother is even older and more evil than him.
* FreudianExcuse: He was abused by his own asshole mother, and also by racist white men.
* {{Jerkass}}: Big time.
* [[spoiler:KarmicDeath: When he tries to hit his son one last time, he succumbs to a back injury, and accidentally falls into his mother's grave, breaking his neck in the process.]]
* KnightOfCerebus: His horrible abuse of Uncle Ruckus is [[BlackComedy darkly humorous]], and yet also quite [[TearJerker crushingly tragic]] at the same time.

!!Jack Flowers
-->'''Voiced by:''' Artt Butler

A government agent who is assigned to stop a terrorist plot in Woodcrest.
* AntiHero: He's a secret agent who kills terrorists for a living.
* {{Badass}}: Comes with being a parody of action heroes.
* CartwrightCurse: He lost the lives of [[DisposableWoman three girlfriends]] to criminals, who killed them in [[StuffedIntoTheFridge gruesomely]] [[BlackComedy hilarious ways]]: the first was beheaded by a swordsman in an alley; the second had a bomb strapped to her and was thrown off a building, exploding in midair; and the third was strapped to a rocket and also blown up in midair.
* EnemyMine: He pursues Huey and Ruckus after mistaking them for terrorists, but when he discovers that they're innocent, they team up to stop the Wunclers' bomb plot against their own building.
* {{Enhanced|InterrogationTechniques}} JackBauerInterrogationTechnique / GroinAttack: His preferred method of getting info out of terrorists is to kick them in the genitals. This inspires Uncle Ruckus to try this on a security guard.
* {{Expy}}: An obvious parody of [[Series/TwentyFour Jack Bauer]].
* ScrewTheRulesImDoingWhatsRight: He defies his superiors' orders not to pursue the Wunclers, [[ScrewTheRulesIHaveConnections who've been deemed]] [[ScrewTheRulesIHaveMoney above the law]].
* ShellShockedVeteran: He says that he can still hear the screams of people that he's killed or {{groin attack}}ed, and feels remorseful about doing this on the wrong people.
* WouldntHurtAChild: Jack tells his boss that he's hesitant about pursuing Huey because he's a kid (saying the trope name word-for-word), although when told Huey might be a terrorist, Jack did threaten to kick him in the nuts (whether or not he would've followed on this threat, we don't know).

!!Dan "The Security Man" Stucky
-->'''Voiced by:''' Louis Lombardi

A private security guard who worked at the Wuncler Tower. Ed I, Ed III, and Rummy conspired to murder Dan with a bomb so they can paint him as a martyr and profit from it.
* AssholeVictim: Almost became one. Lampshaded by Ed I, who calls him a "cocksucker" and a "waste of usable organs", although he planned to give him posthumous good publicity (see below).
* CatchPhrase: "Eat my ass!"
* FakeUltimateHero: Ed Wuncler I planned to make Dan look like a hero who was killed by terrorism, so he can make millions of dollars through a multimedia franchise glorifying him.
* FatBastard / FatIdiot: See HypocriticalHumor.
* GroinAttack / JackBauerInterrogationTechnique: He's the victim of this by Uncle Ruckus, who needed to get a password out of him.
* HypocriticalHumor: He calls a conservative radio talk show to complain about President Obama, claiming that he'll redistribute money to people who "just sit around getting fat and lazy". Guess what he was doing at the same time.
* {{Jerkass}}: Enough to make even the white-loving Ruckus smash his testicles.
* PoorCommunicationKills: He was just trying to tell Ruckus that the password to open a door was "Eat my ass", but Ruckus was confused by this irreverence and stomped him in the nuts.
* SmallNameBigEgo: Even he deluded himself into thinking he's more important than he actually is.
* StrawCharacter: A straw conservative.

!!Pretty Boy Flizzy
-->'''Voiced by:''' Michael B. Jordan

An R&B singer who, much like Usher, seemed to be a threat to Tom's and Sarah's marriage. At the same time though, he gives Tom his own advice about women.
* AllGirlsWantBadBoys: He claims that women prefer abusive jerks like himself, than boring nice guys like Tom.
* DomesticAbuse: He notably beat up his [[{{Expy}} girlfriend]] [[Music/{{Rihanna}} Christianna]].
* {{Expy}}: He's meant to be Music/ChrisBrown.
* {{Jerkass}}: He beats women and taunts about the idea of adultery in your face.
** JerkassFacade: He hired actors to help stage his robberies so that he could stay relevant in the music community. Also does this to provoke Tom into hitting him.
** JerkWithAHeartOfGold: Although he's a trouble-making {{domestic abuse}}r, he did try to help Tom keep his wife. And most of his crimes (besides hitting his girlfriend) were revealed to be staged anyway.
* WhereDaWhiteWomenAt: He has a song called "White Wife Booty". He also intentionally angers Tom by threatening to steal Sarah from him, so that Tom could finally man up.

!!Boss Willona
-->'''Voiced by:''' Jennifer Lewis

A businesswoman and mobster who runs a black women's hair care company. She sells an explosive compound created by the Freemans as hair cream.
* CorruptCorporateExecutive: She knowingly sells poisonous and explosive chemicals as hair care products. Her excuse? She at least places warning labels on the boxes.
* LegitimateBusinessmensSocialClub: She claims that her business is "perfectly legitimate", but later admits that it's "not completely legitimate".
* [[spoiler:StuffBlowingUp: During a confrontation in the desert, Willona accidentally ignites some explosive gases that filled an RV, causing herself and her henchman to get blown up.]]

!!Sturdy Harris
-->'''Voiced by:''' Dennis Haysbert

A civil rights leader who organized one of the Freedom Rides in 1961. He met Robert when he accidentally boarded their bus, forcing him to stay along for the dangerous road trip.
* BadassPacifist: During a race riot in Birmingham, Alabama, he was able to physically defeat several attackers without injuring them.
* DeathSeeker: Robert accused him of caring more about martyring himself for the cause, than the cause itself.
* TheDeterminator: Despite facing all the racist mob violence and spending some jail time, he's determined to keep defying segregation no matter what.
* MadeOfIron: He's easily able to resist several blows from an angry mob due to his huge and muscular frame.
* WellIntentionedExtremist: He may be trying to fight segregation, although he essentially forced an unwilling Robert to join this risky and life-threatening crusade.
* YouCantFightFate: Sturdy insists that God has given Robert the duty to liberate his fellow Negroes, even though Robert has no will to risk his life for it.

-->'''Voiced by:''' GreyDeLisle

An application that came with Robert's iPhone. This Siri is far smarter than it should be, and menaces Robert.
* AIIsACrapshoot: She's scarily intelligent, malevolent, and powerful for an iOS application.
* BitchInSheepsClothing: Stops being helpful after a while.
* DrivenToSuicide: [[spoiler:An attempted murder-suicide. After framing Robert as a jihadist, she orders a drone strike on his house, so they'll live on as spirits. But fortunately Siri is the only casualty.]]
* LoveMakesYouEvil: Well, creepy and one-sided love anyways.
* RidiculouslyHumanRobots: Too human in fact. She even claims to have a soul.
* StalkerWithACrush: She develops an unhealthy obsession with Robert.
* {{Yandere}}: And she'll use any dirty trick to make sure he can't ignore her. It ranges from draining Robert's bank account, posting disgusting photos on his {{Facebook}} page, [[spoiler:to framing him as an Al-Qaeda terrorist]].