Index: Main | Supporting | Recurring | Minor
Robert Kelly's Lawyer
A defense attorney who was hired to defend R. Kelly from charges of sexual contact with a minor (urinating on a teen girl).
- Amoral Attorney: Not only is his client very obviously guilty, but he also uses ad hominem personal attacks against the prosecutor Tom DuBois as part of his strategy.
- Blatant Lies: He denies that Kelly urinated on a teenage girl, despite a videotape clearly showing him committing that act (while giving away his face, name, occupation, and even a Social Security number).
- Chewbacca Defense / Insane Troll Logic: He uses irrelevant arguments for his defense strategy; he argues that ephebophilia isn't wrong, because it was common in America a few centuries ago. He also excuses Kelly by noting that he stuck to his own race, unlike ADA DuBois who married a white woman.
- No Celebrities Were Harmed: He is a parody of defense attorney William Kunstler famous for representing radical activists.
- No Name Given: He is never referred to by any name.
Cristal (like the champagne)
A prostitute whom Robert dated in "Guess Hoe's Coming To Dinner". She works for A Pimp Named Slickback.
- Ambiguously Brown: She has blonde hair and light skin, but speaks with an ebonic accent. Riley calls her a "fake-ass Mariah Carey".
- Big Eater: She packs it away at the Red Lobster restaurant, and then asks for more food when she gets back to the Freeman house.
- Gold Digger: She dates Robert, because he's obviously way above her social class. A song called "Gold Digger" even plays in the background at one point.
- Hooker with a Heart of Gold: Maybe.
- Insistent Terminology: "Cristal, like the champagne."
- Lazy Bum: Huey and Riley complain about how she doesn't do any work around the house, instead just leeching off Robert's food and money.
- Ms. Fanservice: Well it's part of her job after all.
- Only Known by Their Nickname: "Cristal" might not be her real name. Huey notes that girls named after liquor are usually hoes.
- Status Quo Is God: 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: Just your average hooker.
The Health Inspector
An imaginary villain who haunts Tom DuBois' dreams. He's a prison inmate who is constantly trying to rape him.
- All Just a Dream: Fortunately for Tom, the Health Inspector is only a figment of his nightmares. Not that it's any more comforting for him, because of his paranoid phobia of anal prison rape.
- Black Comedy Rape: His whole behavior is Played for Laughs.
- Depraved Homosexual: He really wants to make Tom his "bitch".
- Gag Penis: His dick is so long that it reaches down to the floor!
- Prison Rape: After Tom drops the soap in a prison shower, the Health Inspector demands that he bend down and pick it up...
- Scary Black Man: He's very tall, muscular, intimidating, and well-endowed.
A drug dealer who attempted to murder Gangstalicious. After failing the first time, he and two of his goons chase Gangstalicious and Riley across town to finish him off.
- Gayngster: It turns out that Lincoln and Gangstalicious used to be secret gay lovers; this whole blood feud between them was actually a breakup gone horribly awry.
- Imperial Stormtrooper Marksmanship Academy: When Lincoln and his men finally get their hands on Gangstalicious, they all fire dozens of bullets at him in point-blank range... and they completely miss! Then they just give up on killing him in the end.
- Psycho Ex-Boyfriend: To Gangstalicious, whom he wants to murder after their falling out.
- Straight Gay: In contrast to Gangstalicious, who gradually becomes more Camp Gay.
Huey's teacher at J. Edgar Hoover Elementary, who helps him produce a school Christmas play.
- Nice Guy: He's very polite and genuinely interested in helping out Huey with his project.
- Political Correctness Gone Mad: He is "culturally sensitive" and gives a lecture on Kwanzaa to his bored students, much to their apathy.
- Straw Character: He's a well-meaning but clueless white liberal. Although, he is willing to sacrifice his job so that Huey's performance can be played as Huey intended, which shows some growth on his part.
- Actual Pacifist: Just like he was in real life. However, sticking to his pacifist ideals in the aftermath of 9/11 results in him being branded as a traitor by Fox News.
- All Just a Dream: The entire episode he appears in turns out to have been imagined by Huey.
- Alternate History: Within that dream, it speculates what would happen if King wasn't murdered in 1968, instead getting incapacitated for 32 years, and then waking up and reacting to a whole new world...
- Fish out of Temporal Water: After awakening from his three-decade coma, King has a great deal of difficulty with catching up and adapting to the culture of 21st century America.
- Grumpy Old Black Man: King becomes increasingly disillusioned, frustrated, and pessimistic over the course of the episode. Read below for more info.
- Historical Domain Character: Though his real-life death gets subverted for the sake of this episode's story.
- Take That, Audience! / "The Reason You Suck" Speech: While attending a party filled with many annoying black guests, King finally loses his patience and begins a very fiery rant, scathingly criticizing their behavior.
- Screw This, I'm Outta Here!: After delivering that rant, King has lost all his hope for a post-racial America, so he spends the last years of his life in Vancouver, Canada.
"The Art Teacher"
A painter who gives Riley some art lessons after he's caught spraying graffiti. Ironically, he helps Riley improve his graffiti skills by teaching him how to paint cool murals on houses.
- Affably Evil: He's a very polite, friendly, soft-spoken criminal who goes from being an accomplice to vandalism, to starting a Car Chase with the police, and he even tries shooting at them!
- From Camouflage to Criminal: According to rumor, he's a Gulf War veteran who suffered a nervous breakdown. And not to mention that he gets involved in a crazy chase with the police, while firing a gun at them.
- Funny Afro: He's a white guy with a big blonde afro.
- Hypocritical Humor: He tells Riley that he doesn't like violence. But apparently, trying to shoot at the cops doesn't count.
- No Celebrities Were Harmed: He's a parody of Bob Ross from The Joy of Painting.
- No Name Given: He is never referred to by any name.
- What Happened to the Mouse?: After he assists Riley with his final graffiti mural, he attempts to flee the police by car. Whether he managed to escape, or if instead he got arrested or even killed, is unknown.
Moe "Mo' Guns" Jackson
An old friend of Robert, whom he knew from way back when they served in the US Army Air Forces in World War II. Apparently not a good friend, as they split due to Moe's abrasive personality, and eventually a dispute over a woman they both sought after. After Moe's death, Robert (begrudgingly) attends his funeral in Chicago.
- Armed Farces: Back when he and Robert served in the Tuskegee Airmen, Moe preferred to just goof off by telling bad jokes, while flying around and shooting wildly. This almost got Robert killed during an engagement against the Lutwaffe.
- Face Death with Dignity: His video will shows that he at least didn't lose his sense of humor in his last days.
- Fake Ultimate Hero: He tried to take credit for some of Robert's wartime medals and achievements.
- The Friend Nobody Likes: It turns out that everyone who knew Moe had this relationship with him. Everyone is left wondering what they actually liked about him.
- The Hyena: You'll lose track of how often he laughs at his own stupid jokes.
- Jerkass: He was apparently well known for acting like a dick, and bringing out the worst in everyone.
- Jerk with a Heart of Jerk: In his video will, Moe promised something nice for Robert... which was just a jar of foam peanuts.
- Posthumous Character: Robert remembers him through flashbacks and a video will.
- The Prankster / Troll: Not even his own impending death would end his capacity for annoying jokes and pranks.
- The Tape Knew You Would Say That: Parts of his video will include begging Robert to go through with his wishes, including a pleading glance made until the exact moment Robert agrees to them. And a final laughing fit saved until after Robert received his "inheritance".
Huey's former (best) friend from Chicago. When the Freemans return to Chicago for Moe's funeral, Huey finds out the hard way that Cairo isn't really interested in a reunion, due to Cairo's lingering resentment against Huey for leaving. Things only get uglier from there on.
- Disproportionate Retribution: He treats Huey with absolute disdain simply because he moved away to a white-majority suburban town in another state, something that Huey didn't want and had no say in the matter.
- Jerkass: Cairo insults Huey, calling him a "corny nigga" for moving to "Whitecrest", which provokes Huey into starting a brawl with him. Also see Rejected Apology.
- Rejected Apology: When Huey offers a gift basket to apologize for fighting with Cairo, he spitefully responds by headbutting Huey and giving him a bloody nose. What a dick!
- Those Two Guys: With his new best friend, Dewey Jenkins.
- Ungrateful Bastard: Considering the rather rude way he rejected Huey's sincere attempt to mend their broken friendship.
- We Used to Be Friends: Until Huey's family left Chicago for Woodcrest. When Huey returns, he finds that Cairo doesn't really consider him a friend anymore, as he blames Huey for leaving him behind. Their friendship is definitely broken for good in the ending.
Dewey "Obababa-ooo, Mamma-say, Mamma-sah, Mamma-ma-cu-sah" Jenkins
Dewey is Cairo's new best friend after Huey moved to Woodcrest.
- Dreadlock Rasta: Wears dreadlocks and fancies himself as a revolutionary. Keyword: "fancies".
- Giftedly Bad: He thinks he's good at poetry, but is actually terrible. His poem about death at Moe's funeral is met with Riley booing him, Huey calling him corny, and the rest of the audience looking unamused.
- Jerkass: He acts condescending towards the Freeman brothers because of them moving to a predominantly White neighborhood and mockingly calls them "the Hilton sisters". He's especially condescending towards Huey for not fitting his own superficial standards of being a revolutionary.
- Malcolm Xerox: Like Huey, Dewey is a self-described revolutionary, except he's more shallow in his approach. He believes being "down wit' the struggle" involves reading poetry, wearing capris, headwraps and sandals, and even goes as far as to become a Muslim a reference to Black nationalist Muslim groups like the Nation of Islam and yet he doesn't even know the basic Islamic greeting. Even worse, he mispronounces it as "salami, eggs and bacon", two of which are typically pork products, which are strictly prohibited by Islam.
- No True Scotsman: Dewey criticizes Huey's status as a revolutionary because he doesn't have any poems and is not wearing sandals, headwraps, and capri pants.
- Overly Long Name: Subverted. He introduces himself as Dewey "Obababa-ooo, Mamma-say, Mamma-sah, Mamma-ma-cu-sah" Jenkins, but his name is just Dewey Jenkins.
Shabazz K. Milton-Berle
Shabazz is a Black Panther who was wrongly convicted of, and sentenced to death for, the murder of a cop named Gary Faulkner in 1970. His new pen pal Huey plans to break him out of prison before his execution.
- Angry Black Man: Played with, as Shabazz was a member of the Black Panther Party, though he seems more like a rather mellow guy.
- Cosmic Plaything: Due to the misfortune of simply being in the vicinity when it happened, Shabazz gets incarcerated and scheduled to be killed for a crime he didn't even commit.Shabazz: "Ain't this a bitch."
- Deus ex Machina: Thanks to a sudden blackout caused by a lightning bolt, his execution by electric chair is thwarted. The power then returns just in time for the Governor to call in and commute his death sentence to life imprisonment.
- Miscarriage of Justice: A very extreme case of this. Shabazz was misblamed for shooting Faulkner, even though there was a mountain of evidence left behind by the real killer, Eli Gorbinsky (who even publicly confessed while committing the murder in front of many witnesses).
- No Celebrities Were Harmed: Shabazz K. Milton Berle is an obvious parody of Mumia Abu-Jamal. Both of them are Black Panthers who were controversially convicted and imprisoned for the murders of police officers. Mumia's supporters claim that he's an innocent man who was wrongly incarcerated. According to The Boondocks, Shabazz is a very obviously innocent man who somehow got thrown into prison anyway.
A famous R&B singer whom Sarah and Jazmine are big fans of. Tom becomes concerned when it seems that Sarah (who is increasingly frustrated with her husband) is now developing romantic feelings for Usher.
- Celeb Crush: Sarah has a very obvious crush on him, much to Tom's dismay.
- Mistaken for Cheating: Tom learns that Sarah isn't having an extramarital affair with Usher, she just wanted to take Jazmine to meet him.
- No-Holds-Barred Beatdown: After Tom bitch-slaps him on the face, Usher and his bodyguards retaliate by beating Tom to a pulp.
The spirit of a rapper, who appears to Huey to give him advice on dealing with the ghost of Stinkmeaner.
- Deadpan Snarker: Ghostface makes some rather sharp remarks. For example he has this to say to Huey, who can't believe his own prophetic vision that Stinkmeaner's soul has escaped from Hell for revenge:Ghostface Killah: "What you gonna tell me? Ghosts don't exist? What the fuck do I look like to you?"
- Maybe Magic, Maybe Mundane: Like the White Shadow, Ghostface Killah only appears to Huey, so he might just be a figment of his mind. This gets lampshaded.Stinkmeaner: "Look at that little nigga over there! He talkin' to himself! Haha! You got an Imaginary Friend?"
- Our Ghosts Are Different: Ghostface Killah appears as, well, a ghost. This is immediately lampshaded.Huey: "Ghostface Killah isn't even dead!"
- Spirit Advisor: He serves this role to Huey, in a similar way to the White Shadow. He eventually gives him a solution to ending the Nigga Moment with Stinkmeaner: peace.
Luna is the antagonist of "Attack of the Killer Kung-Fu Wolf Bitch". She was briefly Robert's girlfriend, but turned out to be a deadly martial artist who was emotionally unstable. She doesn't take his rejection well...
- Advice Backfire: Constantly given by her female friend, Nicole. Later in the episode, it becomes so outrageous that it seems Nicole is intentionally giving her bad advice to push her into homicidal rages, either out of loneliness that Luna manages to get dates or simple sadism.
- Affably Evil: Luna is friendly at first and she just wants to date Robert, until he dumps her due to his fear of her abilities. And then she has a Villainous Breakdown.
- And Show It to You: She ripped out somebody's heart back in the Kumite (WA-CHA!), all completed with this line:
- Attempted Rape: After kidnapping Robert, she locks Huey and Riley inside their room, and threatens to sodomize Robert with a broomstick if either of them made a sound. Robert immediately tells them to quiet down after this.
- Ax-Crazy: Oh yes. Especially when she kidnapped and tortured Robert.
- Berserk Button / Hair-Trigger Temper: Any time she thinks that a man has wronged her somehow, whether it's physical or emotional abuse, or just being lied to.
- Blood Knight: She proudly recalls the time that she fought in the Kumite (WHA-CHA!) contest and killed a man with her bare hands, which disturbs the Freemans.
- Broken Bird: Her past relationships has reduced her to this. Her friend Nichole does nothing to help.
- Crazy Canine Lady: Luna owns a pack of three dogs and fifteen wolves, and claims to have them all under her control. Hence Granddad's nickname for her, the "Killer Kung-Fu Wolf Bitch".
- Cute and Psycho: Despite her sexy appearance and overall nice demeanor, she's pretty unstable.
- Cute Bruiser: Definitely. She once ripped a man's heart out with her bare hands.
- Dark Action Girl: As a master of White Lotus Kung Fu, she once overpowered and killed a man much bigger than her. And she later beats the utter shit out of Huey and Robert.
- She mentions becoming a White Lotus master was real hard with a Psychotic Smirk, to which Huey remarks, "They're all dead." His comment insinuated he didn't believe her having learned the style, but the Curb-Stomp Battle quickly proves she was entirely truthful. This leaves the implication that she was the one who killed the masters at some point during or after her training.
- Dark and Troubled Past / Freudian Excuse: Luna was born into a broken household, with an Abusive Dad who beat up her mom over petty reasons like cooking the chicken too cold. She later ran way and dated a series of boyfriends, all of whom were also physically and/or emotionally abusive to her (including a Chinese gangster who ironically enough, also hit her over cooking the chicken too cold).
- Disproportionate Retribution: Luna is easily convinced by Nicole to 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.
- Femme Fatale: Not by choice though.
- Interrupted Suicide: Only most likely because Granddad and Tom were in the same room and tied up when Luna contemplated whether she should blow herself up with a grenade.
- Large Ham: "If I could just find a man to love me-he-he-he-he *gasp* eh-he-he-he-he *gasp* eh-he- *beat* -eee."
- Meaningful Name: Luna is a lunatic. It also invokes the Moon, and her love of wolves.
- Medium Aware: When she arrives at the Freeman's home, her MySpace photo appears beside her and she looks over at it.
- No Guy Wants an Amazon: Though this was more because of how Luna uses her fighting skills for wicked purposes. That is what prompts Robert to cancel his date with her, a rejection that Luna doesn't take very well...
- Obliviously Evil: At least at first. She seems genuinely uncomprehending of how repelling her murderous candor is to regular people, so assumes everything must be wrong with them when they react badly.
- Poisonous Friend Influence: Luna hangs onto Nicole's every word, even if she tells her to kill Granddad, or herself.
- Psycho Ex-Girlfriend: She very quickly becomes one to Robert, when his attempt at dumping her after their first date goes horribly wrong.
- Psychopathic Womanchild: Despite being a very skilled and deadly kung-fu warrior, she's very emotionally unstable due to suffering a lot of unresolved daddy issues / boyfriend problems. After all these years, she's still a sad and insecure little girl on the inside.
- She-Fu: She beats the living shit out of Huey, chokes out Granddad, and tosses Tom across the room by the neck with her legs.
- Skilled, but Naïve: A literal example; she's practically a trained killer, but easily fell for Granddad's Fidel Castro lie.
- Stepford Smiler: First she's a pretty bombshell, then a dangerous psycho, until finally she's just a sad girl.
- Straw Feminist: Her best friend Nicole is convinced that there are no good (black) men. Her beliefs have also rubbed off on Luna.
- Tragic Villain: Her past relationships sucked.
- Unusual Euphemism: Her "friendly sparring match" with Huey wasn't so friendly... for Huey, that is.
- Wham Line: "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 Bitch in Sheep's Clothing: She's beautiful and charming on the surface, but is actually dogshit insane and violent.
- Villainous Breakdown: Triggered by Robert lying to her, she becomes violently angry, but eventually just breaks down into tears.
- Waif-Fu: Luna is also much stronger than she looks, as she is seen beating the crap out of a guy three times her size in the Kumite (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.
- Woman Scorned: She rose hell when she found out Granddad lied to her about attending Fidel Castro's birthday party.
- Yandere: And how.
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.
- Con Man: 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.
- Fat Bastard / Fat Slob
- Forgot to Pay the Bill: Really, Robert neglected to pay the utilities and phone bills in the hopes it would send the New Orleans Freemans packing.
- Karma Houdini: Gets no comeuppance for leeching off Robert.
- Lazy Bum: 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.
- The Load
- Lower-Class Lout: Jericho's family are stereotypical depictions of poor black people; lazy, entitled, uneducated, and having too many kids. Even Riley has a low opinion of them.
- Ragin' Cajun: Lived in New Orleans when the hurricane hit.
- The Tramp
- Ungrateful Bastard: 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.
Catcher Freeman / Catcha Freeman / Tobias Lynchwater
Catcher Freeman is the protagonist of "The Story of Catcher Freeman". According to folklore, Catcher was a freed slave who lived in the 1860s; but the exact details of his story are disputed by Robert, Ruckus, and Huey.
- Action Hero / One-Man Army: According to Robert, Catcher was a militant who actively fought for slave liberation by killing countless slavers with guns, swords, and his bare hands. He also forms a slave militia to attack the Lynchwater plantation.
- Beast Man / Nature Hero: Ruckus described Catcha as behaving like a wild animal, and used the natural environment to his advantage when tracking down runaway slaves; such as smelling their scents like a dog, ambushing them from the water like a shark, and jumping across trees like a monkey.
- Boomerang Bigot / Happiness in Slavery: According to Ruckus, Catcha was a good slave like Tobias, both of them loyal to Massa Colonel. In fact, Catcha was so loyal that he recaptured fugitive slaves and returned them to their owners.
- Composite Character:
- Robert compares Catcher Freeman to Nat Turner, Malcolm X, Barack Obama, and Batman.
- Ruckus depicts Catcha Freeman as essentially a black Tarzan-like figure.
- Huey reveals that the so-called "Catcher Freeman" is actually a partially fictitious character based on Tobias (who took credit for winning the slave revolt, which was mostly the work of the real hero Thelma).
- Dumb Muscle / Manchild: Ruckus claims that Catcha was a simple-minded brute who spoke in the third-person, and was a virgin until he met Thelma.
- Insistent Terminology / Meaningful Name: Ruckus claims that Catcher Freeman's name was actually Catcha Freeman (as in "catch a free man"), because he didn't free slaves, instead he recaptured runaways.
- Memetic Badass: In-universe, Robert and Ruckus both claimed that Catcher was an awesome hero, though for different reasons. Subverted when Huey reveals that Catcher was actually based on Tobias Lynchwater of all people.
- Messianic Archetype: Robert described him as being a charismatic leader who was a hero to all black slaves (except Tobias).
- Posthumous Character: As he died somewhere in the 19th century, presumably of old age.
- Scary Black Man: Robert and Ruckus both believed that he was a tall, muscular, and intimidating negro who could kick your ass.
Thelma is Catcher's lover and later wife. She was a field slave who worked for Massa Colonel, but she eventually assisted in a slave revolt against him.
- Action Heroine: In all versions of the story she plays some role in the slave rebellion, though downplayed with Robert's and Ruckus' tales.
- According to Robert, at the last minute she shoots Tobias with a pistol to save Catcher.
- According to Ruckus, she commanded the other slaves to savagely finish off Massa and his men when they were about to surrender.
- Huey reveals that Thelma personally led the other slaves to battle, and even fought in a sword duel against the Colonel himself.
- Attempted Rape: According to Robert, Thelma was about to be raped by a slave catcher until Catcher stabbed him and saved her. Or according to Huey, Thelma saved herself by grabbing the slave catcher's gun and shooting him before he could rape her.
- But Not Too Black: Thelma is rather light-skinned. Ruckus even claims that she's a mulatto, though this isn't confirmed or denied by Huey.
- Chekhov's Gun: A rather literal example. In Robert's tale, Catcher gives Thelma a revolver to defend herself with, which is later discovered by Massa Colonel. In the climax, she uses the gun to kill Tobias before he could shoot Catcher.
- Damsel in Distress: According to Robert, she had to be rescued by Catcher at least twice, first from some slave catchers, and later from Massa Colonel's forces.
- Femme Fatale / The Vamp: According to Ruckus, she was an evil seductress who tricked Catcha by having sex with him in a barn, and then chained him down so that he couldn't stop the slave revolt.
- Generation Xerox: Huey seems to inherit Thelma's eyes, revolutionary personality, and swordsmanship.
- The Ingenue: Robert stated that she was a pure and saintly woman, unlike the wicked and slutty jezebel that Ruckus claimed she was.
- Love Interest: She serves as the girlfriend (and later the wife) of Catcher. But Huey reveals that she actually married Tobias.
- MadonnaWhore Complex: Oddly enough, she's depicted both ways; a Madonna to Robert, and a Whore to Ruckus.
- Posthumous Character: As she died somewhere in the 19th century, presumably of old age.
A house slave who served as Massa Colonel's right-hand man. He has a one-sided crush on Thelma, but tries to warn the Colonel about the slave rebellion.
- Anachronism Stew: Allegedly, Tobias wrote the first script for a motion picture, a few decades before they were even invented.
- Boomerang Bigot / Happiness in Slavery: He's an "Uncle Tom" house slave who is loyal to his white master. It's no wonder why Ruckus would sympathize with him.
- But Not Too Black: He seems to be the same shade of light brown as Thelma, which is justified due to being George Lynchwater's illegitimate mulatto son.
- Butt-Monkey: He gets no respect from the other slaves (and according to Robert, not even from his own master). However, he somehow gets a happy ending in the true version recounted by Huey.
- Dirty Coward: He's cowardly and somewhat of an opportunist. Also see Fake Ultimate Hero.
- The Dragon: To Massa Colonel.
- Fake Ultimate Hero: At the end of Huey's story, Tobias grabbed a rifle and tried to shoot Thelma, but accidentally killed Massa Colonel instead. Deciding to exploit the slaves' victory, he lied that he killed Massa on purpose, in order to win Thelma's love and the other slaves' admiration.
- Generation Xerox: Robert seems to have inherited his cowardly, opportunistic, and sellout tendencies from Tobias.
- Only Sane Man: Ruckus claimed that he served this role among the other slaves, trying futilely to prevent their evil plot against Massa Colonel.
- Posthumous Character: According to Robert and Ruckus, he was killed during the rebellion. According to Huey, he survived long enough to live as a free man.
- Villainous Crush: He has unrequited feelings for Thelma, who dislikes him for being an Uncle Tom. In Huey's story, he managed to win over Thelma through a little deceit.
- "Well Done, Son!" Guy: He tried selling his movie script to George Lynchwater in exchange for freedom, and perhaps to gain recognition as Lynchwater's son as well.
"Master/Massa" Colonel George Lynchwater
A Confederate Army officer and plantation owner who was killed during a slave insurrection.
- Affably Evil: In the version told by Huey, Lynchwater seemed like a somewhat okay and amiable fellow, despite being a slave owner. He even enjoyed Tobias's screenplay, regardless that he should technically have the slave hanged for being able to read and write.
- Bad Boss: Well he was a slave owner after all. Especially according to Robert, as he had no problem with whipping his own loyal slave Tobias due to a misunderstanding.
- Benevolent Boss: According to Ruckus, Lynchwater provided his slaves with good housing, great food, high living standards; and he didn't even force them do any work, instead he allowed them to goof off and have fun. But the moment he tries to politely request that they do some work, they decide to murder him.
- Big Bad: Massa Colonel is the main villain and antagonist to Catcher Freeman in Robert's story.
- Big Good: But Ruckus flips the above trope on its head, making the protagonist Catcha an ally and servant of the Colonel.
- Colonel Badass: He holds this rank in the Confederate Army, and he seems to be no slouch at combat. In the true story, he gets in a sword fight with Thelma and tries to disarm her.
- Luke, I Am Your Father: It's implied, and later confirmed, that Tobias is the illegitimate son of Mr. Lynchwater and a female slave.
- Off with His Head!: In Robert's tale, he gets beheaded with a sword by Catcher.
- Politically Incorrect Villain: Well he was a slave-owning planter in the Deep South. In Robert's version of the story, he wrongly flogs Tobias for something that wasn't his fault, and forces him to do hard labor with the "field niggers".
- Posthumous Character: One detail that stayed (mostly) consistent through all three stories was that the Colonel was killed in action during the rebellion.
- Suspiciously Specific Denial: In Ruckus's story he tells Tobias: "you've always been like a son to me, except I would never ever lay with your black jungle bunny momma." So of course in Huey's story he's actually Tobias' father.
The evil CEO of the BET network, who plans to destroy black people.
- Ax-Crazy: Completely kill-crazy.
- Bad Boss: She murders two members of her board of directors for pushing her Berserk Button.
- Berserk Button: If she suspects, even for an instant, that you're not being evil enough, she'll kill you very quickly.
- Big Bad: Of the two-part BET saga at the end of Season 2.
- Boomerang Bigot: She outright states that she wants to destroy her own race.
- Card-Carrying Villain: She's only interested in green-lighting TV shows she deems to be evil enough.
- Corrupt Corporate Executive: She runs the BET network like a supervillain organization.
- Evil Laugh: She's got quite a sadistic laugh at that.
- For the Evulz: She loves being evil. And she'll gleefully slaughter anyone who isn't evil enough for her tastes.
- Insistent Terminology: She claims 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: She's a greedy, bigoted, homicidal maniac who kills over the slightest provocation.
- Karma Houdini: 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. Given her career, it's unlikely she was ever punished.
- Laughably Evil: She's a horribly sadistic woman who actively tries to destroy the health of her fellow black people, but she is so wildly over-the-top in her actions that it's hard not to laugh at her.
- No Celebrities Were Harmed: A parody of real BET CEO Debra L. Lee and Dr. Evil.
- Professional Butt-Kisser: She's a shameless kiss-up to her own boss, the President of Viacom (BET's parent company). Strangely enough, her boss isn't bloodthirsty at all, and he may not even be aware of the murders she commits, or her intent to deliberately destroy black people.
- Sadist: Especially shown when she murders one of her board members, grinning and laughing while the blood splashed over her face.
- Slasher Smile: She has two facial expressions: hateful scowling, and a psychotic grin that would make The Joker proud.
- The Sociopath: She's a very greedy and hateful woman, who has no qualms about murdering her own employees.
- Viewers Are Morons: Deborah and her coworkers strongly believe in this concept, so they use BET to keep their audiences perpetually stupefied.
The President of Entertainment for BET. He produces a reality show starring Uncle Ruckus.
- Boomerang Bigot: He hates black people as much as Ruckus does.
- Bystander Syndrome: When Deborah has one of her employees executed, Wedgie seems horrified, but he doesn't intervene out of fear for his own life.
- Corrupt Corporate Executive: Not only is his boss one of these, but he kidnaps a geneticist and (tries to) torture him 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).
- The Dragon: To Deborah Leevil. Though it seems that he continues working for her under fear for his own life.
- Even Evil Has Standards: Zigzagged. It doesn't stop him from doing his job of making BET's shows insulting towards their target audience, but he is still clearly afraid of Deborah's methods, and despite being a Boomerang Bigot, his "good taste" has him make exceptions for people like Gregory Hines and Sammy Davis. Jr, who he finds entertaining.
- Ivy League for Everyone: He boasts about having a business degree from the WASP Harvard University, instead of "one of those historically black colleges".
- Jerkass: He's a proudly elitist, unscrupulous businessman. And he fires an employee for a trivial reason, and takes away his business lunch.
- Motor Mouth: He rambles on and on at meetings, and he even asks if he's speaking too quickly.
- No Celebrities Were Harmed: He's a parody of Reginald Hudlin, who was (very briefly) an executive producer of The Boondocks, before he became the president of BET.
- Professional Butt-Kisser: Likely the reason he was hired, because he doesn't dare question Deborah's crazy and evil schemes.
- Viewers Are Morons: Much like Deborah, he is also a firm believer of this idea. He even proposed a ban on words exceeding three syllables, claiming that more uneducated viewers in the Deep South would have trouble understanding them.
Barack Obama is the 44th 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).
- Celeb Crush: Sarah has a very obvious crush on him, much to Tom's dismay. Also see Celebrity Resemblance below.
- Celebrity Resemblance: Barack Obama is noted to look a lot like Tom DuBois, except the former is more wealthy, powerful, and attractive. It would explain why Sarah voted for him.
- Emergency Presidential Address: 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.
- Hype Backlash: In-universe example: liberal Democrats are enthusiastic about the first African-American President, while conservative Republicans such as 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).
- Obstructive Bureaucrat: He calls Jack Flowers to tell him that he can't arrest Ed Wuncler I.
- Take That!: The show has a decidedly negative view of Barack Obama, depicting his campaign as being nothing more than one big hype machine full of shallow promises.
- And by extension, the Democratic voters (both black and white) who voted for Obama mostly because of his race and those aforementioned shallow promises.
- But the show also mocked Republican voters who were convinced that Obama was a "Socialist Muslim Antichrist" who would bring about America's downfall.
A wealthy businessman from Wushung, China. He tries to settle Ed Wuncler I's massive debt to him by gambling with the outcome of a kickball game between Woodcrest and Wushung; if Wushung wins, then Long-dou will seize all of Wuncler's real estate in Woodcrest.
- Affably Evil: He's very polite and well-mannered for an unscrupulous businessman; and unlike Wuncler, it is seemingly not an insincere facade.
- China Takes Over the World: Or rather, a Chinese businessman tries (and fails) to take over an American town.
- Corrupt Corporate Executive: He bets the financial fate of a city over a sports match. He also bribes the referee to allow his team to cheat.
- Evil Old Folks: He seems to be around the same age as Ed Wuncler.
- Friendly Enemy: He outright states that he respects Wuncler as a Worthy Opponent.
- The Gambling Addict: He's described as one by Wuncler. It's also why they bet Wunclers' debts to him over a sports match.
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.
- Anti-Villain: Invoked; she tells Huey that since she was born, she was forced into a life of playing kickball, and will be sent to a prison camp if she fails this game. But this is subverted, see Manipulative Bitch.
- Little Miss Badass: Ming has been painstakingly trained to do one thing: win at kickball.
- Manipulative Bitch: It turns out that she made up that sob story, in order to trick Huey into going too easy on her. Huey is NOT amused to learn that she made a fool out of him.
- Not So Different: Invoked. Ming manages to psych Huey out for a time by exploiting this trope.
- Serious Business: Her entire life, her function, is kickball.
- Tyke Bomb: Not to bring up kickball again, but say it with us: kickball.
- Worthy Opponent: Huey comes to realize that he's finally up against somebody as furious, ruthless, and determined as he is.
James "Jimmy Rebel"
A white nationalist country singer known for almost exclusively recording anti-black music. Much to his surprise (but not ours), his biggest fan is a black man named Uncle Ruckus. The two become close friends anyways.
- Aesop Amnesia: 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.
- Affably Evil: He may be extremely racist, although he has an otherwise genial personality.
- Bigotry Exception: 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. At the end of the episode, Jimmy admits that he doesn't really hate black people that much anymore. But he still hates Hispanic people though.
- Creator Backlash: He becomes disillusioned with his fanbase by the end, when he realizes that even though he only hates black people because of their attitudes, most of his fans really do just hate them because they're black.
- Deep South: 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 company, Racist Records.
- No Celebrities Were Harmed: He's based on a real racist country singer known as Johnny Rebel. Many of the album titles he lists off at the end have the same names as Johnny's.
Stinkmeaner's old crew of equally nasty senior citizens, who roll into Woodcrest looking to kill the Freemans.
- Avenging the Villain: 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.
- Ax-Crazy: They want to murder an old man and his two little boys for the thrill of it.
- Badass Crew: The three old codgers whoop heaps of ass and kill Bushido Brown. The only thing that can defeat them? Jail.
- Badass in a Nice Suit: Crabmiser wears a full suit, though Pistofferson and Gripenasty are also well dressed.
- Blood Knight: They really enjoy fighting and violence.
- Curb-Stomp Battle: They beat Uncle Ruckus until he's hospitalized. They later prove to be more than a match for the Freemans and decapitate Bushido Brown when he tries to protect the family.
- Evil Old Folks: A whole trio of them!
- Expies: Each of them are based on characters from classic black sitcoms.
- For the Evulz: As they explain, they weren't looking to avenge Stinkmeaner, they just wanted to fuck with any unfortunate victim.
- Jerkasses: 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; they just hate everyone and everything else even more.
- Knight of Cerebus: The Hateocracy are depicted a little less humorously than Stinkmeaner, and they all prove to be among the most dangerous enemies of the Freeman family. Just look at the sheer malice on their faces when they beat two little boys to a pulp.
- Mundane Solution: They may be formidable fighters. But even they aren't outside the law and someone in the neighborhood had enough common sense to call the police who instantly come and arrest them.
- Nice Hats: Each of them wear hats.
- Psychopathic Manchildren: Together with Stinkmeaner, these old geezers are really just overgrown delinquents who delight in causing trouble and harassing other people just for fun.
- Sadists: Like Stinkmeaner, they're delighted by the suffering of other people.
- Sociopaths: And of course, they're utterly devoid of love for anyone, not even for each other.Gripenasty: Just 'cause Stinkmeaner was our nigga, don't mean we gave a shit about his ass!
- Stronger Than They Look: Despite being really old, they seem to be far stronger and more agile than most people much younger than them.
- Terrible Trio: Though they were originally a Terrible Quartet, when Stinkmeaner was still alive and part of the original gang.
- Underestimating Badassery: Riley is skeptically amused by the idea that a gang of old people could be so deadly, until he gets his ass kicked by Gripenasty.
- Walking the Earth: 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 and eventually reuniting.
- Would Hurt a Child: They have no qualms about trying to kill children. George and Esmeralda even attacked Huey and Riley at their school, savagely beating both of them within inches of their lives.
- Vitriolic Best Buds: Though in a twisted way that only psychopaths such as themselves could understand. All four of them were misanthropes who hated everyone in the world, but hated each other slightly less, so they bonded by bullying other people. The surviving three weren't actually interested in avenging their fallen acquaintance Stinkmeaner, they just needed an excuse to harass the Freemans.
"Lord" Rufus Crabmiser
The leader of the gang, he's the bearded man wearing a black hat.
- Badass Beard: Crabmiser has an old sailor's beard.
- Authority Equals Asskicking: Even more so than his accomplices; during the fight against Bushido Brown, Rufus dodged most of Bushido's attacks, and he was the one to land the killing blow on him.
- Badass in a Nice Suit
- Expy: Rufus Crabmiser is based on Fred Sanford.
- Faux Affably Evil: He is the most well-spoken of the group, and is shown to be capable of polite conversation. He even shows his respect to Bushido Brown before their fight. However, it is very clear that he, like his comrades, is a cruel and hateful person.
- Improbable Weapon User: Crabmiser uses a weaponized lobster cage with razor-sharp blades, which he swings and throws around like a flail. He uses it to behead Bushido Brown.
- Nice Hat
- Shown Their Work: His use of crabs as a metaphor for people holding each other back is based on a real phenomenon where crabs will stop each other from escaping a bucket and a theory that is named after it: Crab Mentality.
- Straw Nihilist: Rufus Crabmiser gives a speech to Granddad to this effect, using crab fishing as a metaphor.Crabmiser: "Fascinating creature, the crab. Got that hard exterior, but he ain't really dangerous, except to another crab. Dumb as all hell, can't even walk straight. Matter of fact, the only thing a crab is good for is holding back other crabs. A crab don't wanna see another crab make it. Crab is like, 'If I'm gonna die, we all gonna die.' I admire that. We all gotta die sometimes, might as well help each other get there. I mean, that's what you did to Stinkmeaner. Isn't that right, Robert Freeman?"(Robert panics, and then Crabmiser attacks him.)
- Villain Respect: He considers Bushido Brown to be a Worthy Opponent.Crabmiser: Ah, the legendary Bushido Brown, the greatest black karate man to ever live.
- Villains Out Shopping: Crabmiser enjoys crab fishing in his spare time, though when he's introduced doing this, he's also trying to kill Robert.
"Lady" Esmeralda Gripenasty
The sole woman of the group.
- Adding Insult to Injury: Much like Stinkmeaner, she loves to hurl all kinds of taunts and Trash Talk during fights.
- Bald of Evil: See below.
- Bald Woman: Esmeralda wears a wig, which she loses while fighting Bushido Brown.
- Expy: Esmeralda Gripenasty is based on Aunt Esther.
- Never Mess with Granny: She's a talented martial artist, despite her advanced age.
"Mr." George Pistofferson
The other man of the trio, he's the one with the mustache and blue hat. He's a talented martial artist despite his advanced age. In addition, he's the only one to land a punch on Bushido
A preteen psychopath, whom Riley makes the mistake of hanging out with.
- Abusive Parents: Apparently he was horribly abused by his mom and dad. Inverted with his grandma, who is horribly abused by Lamilton himself!
- Ax-Crazy: He's prone to outbursts of violent rage, and his psychiatrist predicts that he will murder somebody unless he's imprisoned or killed first.
- Bad People Abuse Animals: He fatally shoots Betty von Heusen's guard dog, claiming he was acting in "self-defense", even though the dog was still chained when he tried trespassing into von Heusen's yard.
- The Bully: Even worse than Butch Magnus. Butch would pummel and humiliate his victims. Lamilton would likely straight-up kill them. Even his own grandmother isn't safe.
- Card-Carrying Villain / For the Evulz: See his Catchphrase below.
- Catchphrase: "I'm a bad kid. I like to do bad things."
- Creepy Child / Enfante Terrible: His former school counselor actually suggested that he's The Anti-Christ.
- 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.
- Disney Villain Death: Lamilton falls off from the roof of the J. Edgar Hoover Elementary School building, but this is subverted when his body fat protects him, allowing him to survive with only broken bones and a limping walk.
- Disproportionate Retribution: He beat up his own grandma because she didn't get him fried chicken.
- Drives Like Crazy: Well, what do you expect? He's only eight.
- Expy: Of Henry Evans. Both are false friends of the protagonist, both are sadists 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.
- He's also a parody of Michael Myers due to being labelled by others as pure evil, his lack of empathy and emotion, and having a psychologist obsessed with stopping him.
- False Friend: Lamilton acquaints himself with Riley. Eventually, though Riley, a boy who is very often a Horrible Judge of Character when it comes to befriending people, realizes that there's something very wrong with his "friend", and tries to leave when Lamilton goes too far.
- Fat Bastard: Robert even calls him a "fat fucker". Not to mention the violent tantrum he threw over not getting fried chicken.
- Freudian Excuse: His grandmother states that he came from a very abusive and Dysfunctional Family. Despite this, Lamilton himself never brings up the subject.
- Jerkass: Oh yes, and he can barely hide it. His facade of friendship with Riley is quite shallow.
- Knight of Cerebus: Some of his scenes were among the rare moments not Played for Laughs. His threatening behavior towards Riley was Nightmare Fuel played very straight.
- Lack of Empathy: He makes it clear that he doesn't care about other people.
- Nightmare Fetishist: Lamilton enjoys watching ultra-violent horror movies a little too much.
- No Celebrities Were Harmed: A very transparent parody of Latarian Milton, a 7-year-old kid who also took his grandmother's SUV for a joyride, and had also later beaten up his grandmother for refusing to buy him fried chicken. Many of Lamilton's actions and mannerisms were directly copied from Latarian.
- Obviously Evil: This boy is creepy as all hell; he has a dull and lifeless face, constantly talks about how much he likes doing bad things, and is unable to hide his malevolent nature. His grandmother always thinks that he's just misunderstood, and it took Riley too long to figure out why he shouldn't socialize with him.
- Ominous Latin Chanting: "LAM-IL-TON! TAE-SHAWN!"
- Ordered Apology: On his grandma's orders, he gives a very insincere apology for letting Riley ride with him in his car.
- Sadist: While he doesn't even smile about it, one can tell that he enjoys inflicting torment.
- Smoking Is Cool: He certainly thinks so.
- The Sociopath: His therapist outright considers him to be pure evil. And this assessment is hardly an exaggeration.
- The Stoic: 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: sadistic joy, violent anger, and fear (you too would scream if you fell from a building and got injured).
- Stout Strength: 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.
- Stupid Evil: Lamilton even claims to not 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.
- Troubling Unchildlike Behavior: The most stand-out example of the series so far.
Lamilton's psychiatrist. After studying his anti-social behavior, Doomis became obsessed with stopping Lamilton before he ends up killing someone.
- Critical Psychoanalysis Failure: Lamilton's sociopathy and utter lack of humanity drove Doomis to madness.
- Expy: Of Dr. Loomis from Halloween.
- Kill Him Already!: His preferred solution for dealing with Lamilton, if he cannot be imprisoned or institutionalized.
- Properly Paranoid: While he may be too obsessive about Lamilton and his actions, he is correct that the kid is quite evil.
- Stalker Without a Crush: He closely follows and monitors Lamilton, to the point that Lamilton's grandmother filed a restraining order against him.
- Would Hurt a Child: However, the only child he wants to hurt is Lamilton Taeshawn.
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.
- Bullying a Dragon: He finds himself at both sides of this trope. First, when Riley decides to mock Ripley despite the latter's men aiming guns at him. Then when a gang of Mafiosi barge into his office, Ripley decides to taunt the rival gangsters, which results in his own untimely death.
- Corrupt Corporate Executive: He runs his corporation as a crime syndicate.
- Does This Remind You of Anything?: He runs a chocolate fundraising business as if it was illegal drug trafficking. He even goes so far as hiring thugs to violently harass and intimidate his rivals for daring to sell the chocolate bars for their own separate profits.
- Evil Brit: He's an English expatriate. Invoked by Riley, who mocks every stereotypical aspect of British culture, just to spite Ripley to his face.
- London Gangster: He's not just a mere chocolate salesman, but also a ruthless mobster.
- Politically Incorrect Villain: When surrounded by Italian-American gangsters, Ripley openly taunts them for their ethnicity, even calling them by the slur "wops". This does not end well for him at all.
- Would Hurt a Child: He has no problem with using mobster-style intimidation against schoolkids. He even has guns aimed at Riley and Cindy.
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.
- All Gays Love Theater: And that's just one item of his checklist of gay stereotypes.
- Armored Closet Gay: Winston keeps insisting that he's a heterosexual Christian man, until the end when he admits that he really is just trying to find men to sleep with.
- Camp Gay: No man can be more effeminate than him.
- Celebrity Paradox: He's an expy of Tyler Perry, with Ma Dukes an expy of Madea...but "Or Die Trying" and "The Uncle Ruckus Reality Show" established that Madea movies do exist in this universe, and presumably Perry as well.
- Creepy Crossdresser: He's known for playing a Madea-like character. He claims that God and Jesus told him to make plays and movies while dressed like a woman.
- Expy: Of Tyler Perry and his Madea character.
- No Celebrities Were Harmed: A spoof of Tyler Perry.
- Queer People Are Funny: Pretty much the basis of most of the jokes about him, even more so than Gangstalicious.
- Sinister Minister: His theater troupe is like a quasi-Christian cult, which requires its members to live in a compound, and sever any ties to their old lives.
- Uncle Tomfoolery: His plays and movies make use of a lot of black stereotype humor.
"The Booty Warrior"
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!
- Abled in the Adaptation: He doesn't need glasses like the real-life Fleece Johnson.
- Affectionate Nickname: Played for Black Comedy. The one he has for Chris Hansen is "Chris Handsome."
- Black Comedy Rape: His sexual assault on Chris Hansen is Played for Laughs.
- 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."
- Depraved Homosexual: Was sent to prison specifically because he anally raped Chris Hansen in the middle of shooting To Catch a Predator.
- Even Evil Has Standards: The Booty Warrior doesn't rape children, it was just a ruse to get Chris Hansen. His fellow inmates also wouldn't rape kids.
- Gayngster: He's a perpetually lustful criminal who associates with a prison gang that sodomizes other inmates for fun.
- Gone Horribly Right: While he seemed to have started the Prison Riot on purpose, as it turns out, he simply wanted to anally rape Tom.
- Has a Type: Both the men he was shown targeting were tall, handsome men in suits. In prison, he's less picky.
- No Celebrities Were Harmed: He's based on real life inmate Fleece Johnson, right down to his signature catchphrase.
- Only Known by Their Nickname: Though he's essentially a parodic version of the real-life rapist Fleece Johnson in all but name.
- Prison Rape: Unsurprisingly, anal rape is his only hobby in jail. It's also implied that he's both a perpetrator and victim of this crime. He has zero interest in anything else.
- Rape Is a Special Kind of Evil: He and some fellow prisoners ironically warn the boys about risking a lifetime of getting raped behind bars.
- Scary Black Man: He's not as huge as the "Health Inspector" of Tom's nightmares, but still just as scary.
- Serial Rapist: His only goal in life is to force as many men as possible into receiving anal sex from him.
- Skewed Priorities: 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.
- Stalker with a Crush: 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 (whom he calls "Chris Handsome"), despite knowing that TV cameramen and police officers are waiting for him. And he later starts a Prison Riot, just so he could chase down Tom through the halls of the jail.
- Stupid Evil: Downplayed, he's aware that he's raping Chris Hansen on live television, it's just that he doesn't care about getting arrested for it.
A gardener and landscaper who claims to be the illegitimate son of Robert Freeman and one of his ex-girlfriends (Marietta). Lando and Robert set out to find the truth (and bond together if necessary).
- Butt-Monkey: Not surprisingly, he gets into quite a bit of mishaps when he moves in with the Freemans.
- Luke, I Am Your Father: Billy Dee Williams (the actor who played Lando Calrissian) reveals himself to actually be Lando's father.
- Luke, You Are My Father: He claims to be the bastard son of Robert and Marietta, born circa 1980. According to a DNA test however, Lando is in fact NOT the son of Robert Freeman.
- Meaningful Name: Lando sharing a name with Star Wars character Lando Calrissian is noted, while Lando mentions that around the time he was conceived, his mother and father watched The Empire Strikes Back. In fact, the actor who played Lando Calrissian is his real father.
- Nice Guy: Overall, he's a very friendly guy. 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).
Robert's Girl of the Week 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.
- 100% Adoration Rating: 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 ex-girlfriends), nor even the black-hating Ruckus (who develops his own crush on her), can find any genuine faults about Ms. Brown.
- The Ace: Bordering on Parody Sue. Ebony Brown is athletic, beautiful, kind, smart, and successful. Essentially, a perfect woman.
- Meta Girl: She lampshades the show in a Leaning on the Fourth Wall kind of way. She finds Robert Freeman's life stories about all his crazy misadventures and the wacky people he's met to be very entertaining. She even asks if she can be a "main character" in his life.
- Nice Girl: She does a lot of humanitarian work overseas, and is probably the most good-natured person that Robert has ever met.
- Parody Sue: Ebony Brown can be interpreted as being an Affectionate Parody of Mary Sue Fan Fiction (regarding both this show and others) because, by this show's standards, she's just so damned perfect.
- She's Robert's latest girlfriend, but miraculously bucks tradition by being genuinely more kindhearted, sane, and levelheaded than anyone else around her; as well as being so strikingly beautiful, that even Uncle Ruckus puts a lid on his racism for once, and falls arse-over-tits for her.
- She repeatedly leans on the fourth wall, and expresses a desire to become a major part of Robert's life (similar to a Self-Insert Fic character joining the main cast out of nowhere).
- Robert falls completely in love with her, and becomes madly obsessed with their relationship together, despite the fact that they only met a short while ago (a satire of shipping stories where characters are Strangled by the Red String); and their relationship is played up for all the hamfisted melodrama that can be wrung from it (satirizing the Romantic Plot Tumor nature of the aforementioned shipping stories).
- Also, Ebony shares her name with one of the most infamous Mary Sues in fan-fiction history. It's not known if this is an intentional reference or not, but it would make it all the more blatant if it was.
- Why We Can't Have Nice Things: Despite all this, Robert's paranoia that Ebony doesn't find him attractive enough derails their relationship.
- World's Most Beautiful Woman: As part of the entire joke about how impossibly perfect she is, and in addition to having a great personality, Ebony is an extremely attractive, physically fit young woman. Even Uncle Ruckus, who generally believes that black women are ugly, admits that she is very pretty despite being a member of an "inferior" race.
- Big, Screwed-Up Family: They're so extremely and horribly dysfunctional, that even the Freeman family note how much better they themselves seem compared to the Ruckuses.
The mother of Mister Ruckus, and the paternal grandmother of Uncle Ruckus. She's just as ancient as she is hateful.
- Abusive Parents: She raised Mister to be an asshole much like herself. She's also an Abusive Grandparent, as she smacks Uncle, and attacks one of his younger brothers with a knife.
- The Chain of Harm: She's responsible for how her son turned out, and in turn her grandson. It's not discussed, but it's most likely that her childhood was nothing good either.
- Death Seeker: For most of her life, she's been waiting to die of old age. Her wish is finally granted when she passes away while sitting in Robert's living room chair. Her only regret is that she was outlived by her hated son.
- Evil Old Folks: Possibly well over 100 years old when she died.
- Jerkass: Uncle notes that she's even nastier than Mister, and that's really saying something.
- Knife Nut: She intends to die in Robert's chair despite his dismay. So she threatens everyone with a straight razor, and slashes the hand of one of the Darrel/Darryl twins.
- Misanthrope Supreme: She hates just about everyone around her, including her entire family.
- The Sociopath: She's very open about her hatred and apathy for all people. Not to mention how ruthlessly and unlovingly she "raised" her son.
- Straw Nihilist: She rants on about how she thinks life is nothing but cruel and meaningless, which is why she doesn't want to live any longer.
The father of Uncle Ruckus. Uncle hates his dad with a passion (and with good reason).
- Abusive Parents: To extreme levels. Mister Ruckus was an angry drunkard who had frequently beaten a much younger Uncle Ruckus for little or no reason. Eventually, he personally dragged and threw his own son out of the house.
- Berserk Button / Hair-Trigger Temper: The mere existence of his son Uncle Ruckus seems to be this for him, and often took the slightest excuse to violently strike him.
- Catchphrase: "Nigga, did I just catch you [doing something]?!" (slap)
- The Chain of Harm: He learned well from his mother on how to mistreat his own kids.
- Evil Old Folks: Old age has not watered down his asshole behavior. However, his own mother is even older and more evil than he is.
- Freudian Excuse: He was abused by his own asshole mother, and also by racist white men.
- Jerkass: Big time. Despite having a tragic backstory of his own, not once is he shown as being redeemable.
- Jerkass Has a Point: As awful as he is, he correctly points out the fact that his entire immediate family are, in one way or another, completely subservient to white people... and it pisses him off.
- Karmic Death: When he tries to hit Uncle one last time, he succumbs to an old back injury; causing him to accidentally fall into his mother's grave, while breaking his own neck in the process.
- Knight of Cerebus: His horrible abuse of Uncle Ruckus is still darkly humorous, but yet also quite crushingly tragic at the same time.
- Last Disrespects: He attends his mom's funeral, because it's the event he's been gladly anticipating for his whole life. Uncle Calling the Old Man Out even boils down to encouraging this to make him stop treating them the same way.
- Laughably Evil: Takes child abuse to ghoulishly comedic extremes.
- Misanthrope Supreme: He really doesn't like other people at all. He may not even care for himself, as his behavior suggests a lot of self-loathing.
- Politically Incorrect Villain: Mister is a racist old man, though at heart he's probably another "hates everybody" misanthrope like Nelly or Stinkmeaner.
- He hates white people, though this is because he spent most of his life living under segregation, getting physically abused by white men.
- He also disparagingly labels Uncle as a "professional Mexican" for having so many different menial jobs. (Although this is rather hypocritical, as Mister himself was a menial servant when he was younger.)You still ain't got shit, and ain't never gonna have shit. You know what that makes you? A Mexican. Is that what you've accomplished with your life boy? Being a Mexican? You ain't even gotta speak English to be a Mexican! Whose fault is it that you're a professional Mexican? Is that my fault?
- "The Reason You Suck" Speech: Lays a cruel but accurate verbal beatdown on his family during their dinner, particularly Bunny and Uncle Ruckus:Mister: Shut your ass up, Bunny! I'm sick of you talkin' about that goddamn white man all the time. Name one of them who ever did shit for any of you. Huh?
(Bunny puts her head down in shame)
Mister: Can't do it, can you? Look at what you did. All my kids is some damn Uncle Toms.
(Looks at his kids and finally addresses Uncle)
Mister: And you're the worst! A black fool who hates himself so much, he can't even see what's in front of him in the mirror. Just another black nigga like the rest of us.
- Later in the climax, Mister himself is at the receiving end of a speech like this (see "Calling the Old Man Out" in Uncle Ruckus' section).
- The Sociopath: What else do you call someone who willingly throws away their own innocent child, without any hint of hesitation or remorse?
- Tough Love: The Darrel/Darryl brothers suspect that Mister's abuse could have been his own twisted way of toughening them up for a tough world.
- Tragic Villain: Considering how hateful his mother is, it's small wonder the man has his fair share of problems.
The mother of Uncle Ruckus. She loves her children, but also loves white people more than her own race.
- Accentuate the Negative: Here's an example when she tried to teach history to Uncle:Uncle: Mama, who was George Washington Carver?
Bunny: He's the man responsible for more peanut allergy deaths than anyone who ever lived.
- Adults Are Useless: She may have loved all three of her sons, but was utterly worthless as any sort of proper role model.
- Boomerang Bigot: While Bunny doesn't hate black people, she still thinks that they're inferior to white people. This helped influence Uncle's warped worldview.
- Both Sides Have a Point: Her husband may be right about the family being subservient to white people, but it at least meant that their sons didn't grow up to hold a grudge towards them like he did. Uncle was only one who became an actual racist compared to her, Darrell, and Darryl anyway.
- Catchphrase: (After Mister slaps Uncle) "Lord have mercy, my baby!"
- Dark-Skinned Blonde: She dyed her hair blonde, and eventually got blue eye contacts to match.
- Karma Houdini: She gets off scot-free for making her son racist, and being a useless bystander to the abuse her husband suffered, which led to him taking it out on Uncle.
- MayDecember Romance: After her husband's death, Bunny decides to engage her significantly younger white boyfriend.
- Useless Bystander Parent: Responsible for Uncle Ruckus' internalized racism, and also not providing her husband with emotional support after the abuse he suffered from his mom and white men, and at the same time, failed to stop her husband's subsequent abuse of his son.
Darrell and Darryl Ruckus
Uncle's younger twin brothers. Despite growing up in such an unhappy family, they became functioning members of society.
- Alliterative Names: In fact, their names are homophones only differentiated by a few letters.
- Always Identical Twins: Their appearances are only differentiated by their clothing.
- Nice Guys: They're always very polite and respectful, despite the stressful family drama around them.
- Only Sane Men: They're the only ones in the Ruckus family who didn't grow up to be jerks and/or self-racists. Although their dad accuses them of being "Uncle Toms".
- Shout-Out: Darrel is dressed like Fat Albert and Darryl like Mr. T.
- Token Good Teammate: At any rate, they seem to be the least pathetic excuses for human beings in their family.
- Where Da White Women At?: One of them is married to a white woman, something which Bunny is proud of. Though considering the way she raised them with the "white = better" mentality, this was probably an inevitable subconscious result of their upbringing.
Agent Jack Flowers
A federal government agent who is assigned to stop a mysterious terrorist plot in Woodcrest.
- Action Hero: Jack is a parody of spy thriller protagonists.
- Memetic Badass: In-universe, he's developed a fearsome reputation for his skills at fighting terrorists and kicking their testicles. But Huey wasn't aware of who Jack was until they met, though Ruckus already heard about him.
- Anti-Hero: He's a secret agent who tortures and kills terrorists for a living. He seems ruthless at first, though he's actually morally conflicted about his job.
- Cartwright Curse: He feels guilty about not being able to prevent three of his girlfriends from getting brutally murdered by criminals:
- Tracy was decapitated by a swordsman in an alley.
- Eleanor had a bomb strapped to her, and was thrown off a building, exploding before hitting the ground.
- Taquanda was strapped to a missile, and was flown and blown up in midair.
- Enhanced Jack Bauer Interrogation Technique / Groin Attack: 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 Jack Bauer.
- Fire-Forged Friends: After a confused counter-terrorism operation gone wrong (Jack Flowers mistakenly believed that Huey and Ruckus were terrorists), Jack convinces Huey and Ruckus to help him out by evacuating Dan Stuckey from the Wuncler Tower before a bomb destroys it.
- Rogue Agent: Jack Flowers decides to go vigilante on the Wunclers.
- Shell-Shocked Veteran: He says that he can still hear the screams of people that he's tortured or killed, and feels especially remorseful about accidentally harming innocents.
- Wouldn't Hurt a Child: Jack tells his boss that he's hesitant about pursuing Huey because he's a kid (saying the trope name almost word-for-word). Although after he was 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).
Daniel "Dan the Security Man" Stuckey
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.
- Asshole Victim: 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 Fake Ultimate Hero).
- Catchphrase: "Eat my ass!"
- Fake Ultimate Hero: Ed Wuncler I planned to make Dan look like a heroic martyr who was killed by terrorism, so that he can make millions of dollars through a multimedia franchise glorifying him.
- Fat Bastard: Looks to be just as obese as Uncle Ruckus (who he gets in a fight with), and has a similarly unpleasant personality.
- Fat Idiot: He's really not as much an expert in politics or business as he arrogantly believes himself to be.
- Hate Sink: An odd play on the trope from Ed I, as killing Dan in a fake terrorist attack would make him into a "hero" who died doing his job; and due to how much of a fat whiny asshole he really was, no one would personally care if he is dead. Basically he'll make a good martyr, because dying is the best thing Dan could ever do.
- Hypocritical Humor: 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 — munching on a hamburger while watching TV on the job.
- Jerkass: He's very rude and has an (undeservedly) large ego.
- Poor Communication Kills: He was just trying to tell Ruckus that the password to open the front door was "Eat my ass", but Ruckus was confused and irritated by this apparent irreverence, so he stomped him in the nuts.
- Small Name, Big Ego: Even he deluded himself into thinking he's more important than he actually is; when calling the aforementioned radio show, he makes himself out to be a brave trooper "protecting the front lines" of American capitalism, and thinks he can become just as filthy rich as his employer Ed Wuncler. When really, he's no more than just a lazy rent-a-cop.
- Straw Character: Another unflattering stereotype of conservative Republicans.
"Pretty Boy Flizzy"
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.
- All Girls Want Bad Boys: He claims that women would prefer abusive jerks like himself, rather than boring nice guys like Tom.
- The Casanova: He's a notorious womanizer, and it really shows in his music (most of his song titles and lyrics are very sexually explicit).
- Celeb Crush: Sarah has a very obvious crush on him, much to Tom's dismay. Noticing a pattern here?
- Domestic Abuse / Would Hit a Girl: He notably beat up his girlfriend Christianna. Of all the crimes he was charged with, Flizzy admits to this being true.
- Hidden Heart of Gold: 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.
- Jerkass: He beats women and taunts about the idea of adultery in your face.
- Jerk with a Heart of Gold: Although he's a trouble-making domestic abuser, he did try to help Tom keep his wife. And most of his crimes (besides hitting his girlfriend) were revealed to be staged anyway.
- Mr. Fanservice: Something which he boasts about a lot, hence his stage name.
- No Celebrities Were Harmed: He's meant to be Chris Brown.
- Obfuscating Stupidity: Pretty Boy Flizzy only acts like an idiotic jerk, just so he can get higher up on the ladder in the music industry, and maintain his status among his fanbase.
- Only Known by Their Nickname: "Pretty Boy Flizzy" is his stage name.
- Where Da White Women At?: 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.
A businesswoman and mobster who runs a hair salon for black women. She sells an explosive compound created by the Freemans as hair gel.
- Corrupt Corporate Executive: She knowingly sells poisonous and explosive chemicals as hair care products. Her excuse? She at least places warning labels on the boxes.
- Legitimate Businessmen's Social Club: She claims that her business is "perfectly legitimate", but later admits that it's "not completely legitimate".
- Stuff Blowing Up: 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.
An elderly woman from a nursing home who gives Robert a job of being a male "escort" (prostitute) to lonely younger women.
- Jerkass: Geraldine is a madame (female pimp) after all, and she's willing to harshly punish Robert for his mistakes.
A 39-year-old woman whom Robert meets while working as an escort for Geraldine.
- Nervous Wreck: She's very insecure, partly due to still being single for a woman her age.
Reverend Sturdy Harris
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. Appears in "Freedom Ride or Die".
- The Ace: He is a graduate student from Fisk University, captain of its football team, charismatic to his followers, and a huge man who is built like a tank.
- Badass Baritone: His voice is fittingly deep for a man of his size and courage.
- Badass Pacifist Preacher: During a race riot in Birmingham, Alabama, he was able to physically defeat several attackers without injuring them.
- Death Seeker: Robert accused him of caring more about martyring himself for the cause, rather than the cause itself.
- The Determinator: Despite facing all the racist mob violence and spending some jail time, he's determined to keep defying segregation no matter what.
- Fearless Fool: Sturdy never hesitates from taking risks, and he never worries about danger.
- Gentle Giant: Sturdy is a very tall, wide, and strong man who never uses his muscles to inflict pain on anyone. Well, aside from manhandling Robert to force him to stay with his group.
- Made of Iron: He's easily able to resist several blows from an angry mob due to his huge and muscular frame.
- Suicidal Pacifism: Willingly faces racist mobs and trigger-happy police with no clear goal.
- What Happened to the Mouse?: During the episode's frame story (a present-day documentary consisting of interviews of Robert and the other Freedom Riders), Sturdy is nowhere to be seen, except in the flashbacks to 1961. Though unconfirmed, it's possible that he's deceased.
- You Can't Fight Fate: Sturdy insists that God has given Robert the duty to help liberate his fellow Negroes, even though Robert has no will to risk his life for it.
- Cruel and Unusual Death: After getting a few too many silicone butt implants, her ass explodes. She dies slowly and painfully in the hospital.
- Hartman Hips: Played for Laughs, Kardashia has a massive fake ass that is apparently very dense and destroys everything it comes in contact with.
- Jerkass: Not surprisingly, she's a petty and shallow woman who's desperate for reality TV stardom, not caring about what it takes to get there.
- No Celebrities Were Harmed: Of the Kardashian sisters.
- The Reveal: She's not actually related to the Kardashians. Everyone leaves her behind, so she dies alone with her dreams crushed.
An application that came with Robert's iPhone. This Siri is far smarter than it should be, and menaces Robert.
- A.I. Is a Crapshoot: She's scarily intelligent, malevolent, and powerful for an iOS application.
- Bitch in Sheep's Clothing: She stops being helpful after a while.
- Driven to Suicide: 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.
- Hollywood Hacking: She can take over any piece of technology, which she uses to spy on Robert and harass him into "loving" her back.
- Love Makes You Evil: Well, creepy and one-sided love anyways.
- Our Spirits Are Different: While Robert is trying to sleep, he sees Siri in the form of an ethereal blonde woman.
- Ridiculously Human Robots: A little too human in fact. She even claims to have a soul.
- Stalker with a Crush: She develops an unhealthy obsession with Robert and tries to force him into loving her, up to and including getting a wedding.
- 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, to framing him as an Al-Qaeda terrorist.
Clone of Colonel H. Stinkmeaner
The clone of Colonel H. Stinkmeaner, created in an illegal underground laboratory. The original Stinkmeaner posthumously gives him instructions to start a new Nigga Moment with Robert Freeman.
- Avenging the Villain: Subverted. The clone never knew the original Stinkmeaner, he just thinks that his only purpose in life is to annoy Robert Freeman like his predecessor did. After the clone is defeated, Robert decides to make peace with him:Stinkmeaner's Clone: "Well sure, all you had to do was ask. I don't even know you, I'm just the clone."
- Handicapped Badass: The clone also seems to be blind, however he has enhanced strength and martial arts skills. Although Robert trains hard enough to defeat the clone in a rematch.
- Born as an Adult: The clone is confused as to why he's an old man biologically, despite only being a few years old chronologically.
- Cloning Blues: Subverted, as he doesn't really feel any different knowing he's a clone, only that he's alive and the other guy's dead.
- Evil Is Hammy / Laughably Evil: Just like the original!
- Jerkass: Just as mean as the first Stinkmeaner.
- Rooting for the Empire: In-universe example. Stinkmeaner's clone gets a large fan base who support his side of the Nigga Moment against Robert.
A gay rights activist who was a former associate (and protege) of Rollo Goodlove. After Riley is accused of being homophobic towards a fellow student, Sweetlove tries to force him to apologize.
A mental disability activist who, after learning that Riley is a "special needs" kid, note asks Riley to join a footrace with other "special" children.
- Berserk Button: He's furious whenever Riley says the word "retarded".
- Ditzy Genius: Philbert seems to have some kind of mental handicap or illness himself, but he's smart enough to lead a special interest organization (and much like Walter and Rollo, he knows how to extort people). He's also an amazing artist, able to draw a very elaborate sketch in just a few minutes.
- Greed: He's really more concerned about money than politics.
- Ink-Suit Actor: Has a very uncanny resemblence to Tommy Lister.
- Manchild: His preference for Strawberry Milk makes him seem like one, especially when he's drinking it from small milk boxes.
- Scary Black Man: He's a huge and buff negro who can be quite scary when he's angry.
- Straw Character: Yet another straw activist.
- Trademark Favorite Food: He really likes Strawberry Milk.
- Would Hurt a Child: Ruthlessly grabs Riley by the collar and throws him to the ground, leaving him at the mercy of several other special needs kids after Riley decides he doesn't wanna be in the race anymore and calling the other kids retards.