List of The Boondocks characters
Main fictional characters
The Freeman family
Huey Freeman (voiced by Regina King) is a young leftist radical black revolutionary and retired domestic terrorist. He is a practicing swordsman and near master practitioner of Chinese martial arts, as seen in the episodes "Let's Nab Oprah", "Attack of the Killer Kung Fu Wolf Bitch", "Stinkmeaner 3: The Hateocracy", and "...Or Die Trying". He maintains an austere, yet strangely loving relationship with his brother Riley, and has shown the willingness to go out of his way to prevent his brother from succumbing to bad influences (occasionally giving him some "tough love"). Over the course of the comic strip and television series, Huey retains a sober demeanor, tending not to let his countenance relay his mood. During most episodes, Huey takes on the role of narrator, and it is often only through his narration that his thoughts and emotions are revealed. In the comic strip, Huey's best friend was Michael Caesar, who effectively balanced out Huey's pessimistic world outlook with his upbeat personality and temperament. The role he played in Huey's life has been taken up by his neighbor Jazmine Dubois in the television series. Unlike Caesar, Jazmine tries to balance Huey's demeanour with a childlike, naive innocence, which often leads to Huey having to resolve a situation where Jazmine is being taken advantage of.
Riley Freeman (voiced by Regina King) is Huey's younger brother. Riley could be described as a product of mass media influence, in that he refers to women as "bitches" or "hoes", frequently alludes to his "rep" and his status on the "streets", and idolizes gangsta rappers and their lifestyle. He often refers to himself as self-appointed moniker "Young Reezy". Though he would seem to be everything his brother is not, he has demonstrated his ability to rationalize and plan things out, such as when he planned his "fund raiser" and when he rendered attorney Tom Dubois speechless after debating with him regarding the R. Kelly trial in "The Trial of R. Kelly". "Damn, you just got beat by an eight year-old." which Huey remarked. His criminal aptitude is put to the test when he goes on some crime sprees with the incompetent Ed Wuncler III and Gin Rummy in the episode "Let's Nab Oprah" during which he effectively acts as the brains behind the operation to kidnap Oprah. Riley can be seen as representative of the misguided black youth. He has a fascination for firearms, and his tendency for violence is displayed time and time again. At Christmas, he declared himself "The Santa Stalker" and attacked the Santa at the local mall with airsoft Glock 17s, hitting many innocent bystanders. Riley does not own any real firearms and has only been seen owning Airsoft-style guns—a Glock 17 and an MP5K—but he pals around with Ed Wuncler III and Gin Rummy, who have on occasion granted him access to real weapons. He also seems to possess unusually large amount of strength and stamina, as seen when he fights his brother Huey, who is a very high degree martial artist and swordsman. It can also be seen when he fights Stinkmeaner alongside his family where, albeit slow, his blows seem to be worth blocking against a kung-fu trained Stinkmeaner. Indeed, though, beyond this tough-guy facade, there would seem to be some measure of sensitivity that is especially apparent in the episode "Riley Wuz Here" during which he learns to use his incredible artistic abilities to create art for the sake of creating art, and not for personal glory.
Robert Jebediah "Grandad" Freeman
Robert Jebediah "Grandad" Freeman (voiced by John Witherspoon), is the paternal grandfather and legal guardian of Huey and Riley who lives in a peaceful environment and tries to enjoy his retirement. Robert has born witness to many major incidents in American history. He was a part of the Civil Rights Movement, but was prone to certain faux pas such as donning a raincoat in preparation for getting doused by a police fire hose. Robert was also a fighter pilot in World War II, during which time he flew a P-51 Mustang with the Tuskegee Airmen. He was also a part of the Montgomery Bus Boycott, even sitting next to Rosa Parks, though she received all the credit for refusing to give up her seat while he, having actually refused before her and much to his chagrin, received none. This also brings Robert's age into question, since in order to have been in WWII and in the Civil Rights moments he claims to have been in (while making his relative stamina and cartoonish actions realistic), he would be between 87 (the minimum age of World War II participants of 1945) and 100 years old today. Granddad occasionally serves as a more pragmatic voice of reason. Though he has expressed his embarrassment over Huey and Riley, and though he sometimes gets distracted with his unending quest for a younger wife, his primary motivation is to advance his family's best interest. This is where he most often finds himself at odds with his grandsons. Huey and Riley, though possessing contrasting personalities, tend not to act in a manner in line with their grandfather's desire for simplistic living. Riley gets in trouble a lot, and Huey always has his eye on some bigger picture. As a guardian, he does not hesitate to use corporal punishment where necessary. Although it is never directly explained how Robert came to be Huey and Riley's guardian, it is implied that Huey and Riley's biological parents are deceased.
Secondary fictional characters
The DuBois family
- Thomas Lancaster DuBois (voiced by Cedric Yarbrough) - Tom DuBois is the Freemans' wimpy, geeky across-the street neighbor who works as an attorney. He is an African-American, whose character is a stereotype of a successful white-collar Caucasian man. Skittish and easily frightened, Tom adheres strictly to the law because of his virgivitiphobia, the fear of being anally raped in prison, as Huey's narration explains in "A Date With The Health Inspector": a flashback shows 10-year-old Tom being terrified by a prison movie he's watching on TV; from then on, he refuses even the slightest legal infractions ("But what if we get caught? We'll get arrested and anally raped!"). Huey mentions that Tom's job as a prosecutor sends other black men to the very fate he most fears. He also played basketball in college. His character can be interpreted as an "Uncle Tom" as he is seen as having turned his back on his black heritage (however genealogical testing shows him as being 32.5% Scottish) to marry a white woman (Sarah), producing a mixed-race child (Jazmine), and becoming a criminal prosecutor who often convicts black people. But in line with the show's complexity, the name "Dubois" may be an homage to W. E. B. Du Bois, thus putting his character in a state of conflict. For example, in one episode the neighborhood watch was convinced of the Freeman family's guilt in a string of local break-ins due to their reluctance to speak to the police, and Tom, rather than acquiescing, confronted the neighborhood watch with the ridiculous nature of their accusations. Tom was at one point the unwilling vessel for Stinkmeaner after Stinkmeaner's escape from Hell; however, Stinkmeaner was eventually exorcised which returned Tom to normal. Various episodes depict Tom as a supporter of LGBT rights, gun control (or at least proper gun registration), and protection of Intellectual property.
- Sarah DuBois (voiced by Jill Talley) - Sarah is Tom's white wife. She is very comfortable about their interracial marriage even when Tom is mocked for it in "The Trial of R. Kelly". She even jokingly said to Tom, "I told you about messin' with them white women". Sarah and her daughter are Usher fans, which makes Tom jealous. Several episodes imply that Sarah is sexually frustrated when Tom's jealousy over Usher forced Sarah to throw him out of the house.
- Jazmine DuBois (voiced by Gabby Soleil for first 3 seasons, Kiarah Pollas for season 4) - Jazmine DuBois is Tom and Sarah's biracial daughter. She can be extremely paranoid and a bit naive, making her an object of ridicule for Riley. Jazmine was shocked by both the September 11 attacks (and hid in her room for two years as a result in the comic strip) and finding out that the tooth fairy is not real. She is a strong believer in Santa Claus, viewing him as the true meaning of Christmas to the point where she dreams of preaching the gospel of Santa to the masses. Huey can sometimes be cold toward her and this is shown through her constantly following him around. She first appears in the episode "The Trial of R. Kelly".
Other major fictional characters
- Michael Caesar (known by his surname) is Huey's classmate and best friend throughout the comic strip. Formerly from Brooklyn, New York, he was moved to the fictional predominately white suburb of Woodcrest under circumstances similar to Huey's; he typically needs little prompting to vocally represent his hometown. He and Huey have co-founded the newsletter The Free Huey World Report and the annual Most Embarrassing Black People Awards.
- Uncle Ruckus (voiced by Gary Anthony Williams) - Uncle Ruckus is the main antagonist. Overweight with a grotesque appearance and a glass eye (It is also implied that he may possibly be senile.), he idolizes old black-slave culture. Ruckus is self-hating, disassociating himself from his African-American heritage as best he can, and hates all non-white people. His greatest wish is that black people were still enslaved, because he believes that they were better off. His views of black people align with the views of white racists. He claims to have a mythical disease called "re-vitiligo" ("It's the opposite of what Michael Jackson's got, lucky bastard" he always retorts). The episode "The Garden Party" strongly evidences his hatred of black people to the point that when Riley, Huey and Granddad arrive he exclaims "We have a 'code black' at the main gate". During that episode, Ruckus performs an impromptu song entitled "Don't Trust Them New Niggas Over There." Not only is Uncle Ruckus racist toward blacks, but he seems to be a white supremacist and an extreme racist which is strongly shown in "The Red Ball", where he claims that Ed Wuncler Sr.'s "White leadership" helped the team win the game and refers to a Chinese man as a "yellow nigga". Ironically, he is the show's darkest-skinned character. His character is a hyperbolic parody of the self-hating black man. However, as much as he may hate black culture, other episodes show him socializing with the Freemans. In "…Or Die Trying", he demonstrates a mastery of the nunchaku and hand-to-hand combat. In "The Uncle Ruckus Reality Show", he is horrified to learn via a DNA test that he is 102% African with a 2% margin of error. The knowledge of his true heritage causes him to quit all of his jobs (he is seen in a variety of service jobs in the show) and adopt other behaviors that conform with his racist views. Later in the episode he is shown false documents stating that he is 52% white after the executives in charge of the show become upset over the plummet in ratings that Ruckus' behavior caused. He is told the original results were performed by a black doctor and were erroneous. In "Good Times," Uncle Ruckus started his campaign to run for mayor.
- Ed Rothschild Wuncler, Sr. (voiced by Edward Asner) - Ed Wuncler Sr. is an overweight, rich realtor who is the father of Ed Wuncler Jr. and the grandfather of Ed Wuncler III. His family founded the town of Woodcrest and have lived in the area for over a century. His last name draws on the character “the Once-ler” from Dr. Seuss's book The Lorax. Like his namesake, Wuncler acts as the hyperbolic archetypal capitalist. He praises the freedom to exploit cheap labor and complains about high taxes in "The Block is Hot". The wealthy Wuncler owns the loan on Granddad's house (as he does with every house in Woodcrest) and somehow Woodcrest's police force, and is embarrassed by Ed Wuncler III. Wuncler sometimes does things considered racist such as referring to Grandad as "Robert Freedman", and employing only illegal Mexicans at his restaurants. Ultimately, though, his racism is implied as simply being a byproduct of his insatiable greed rather than an active hatred of those from different races. Ed seems to have taken a general liking to Robert, referring to him as "Old school", and even funding his Soul food Restaurant venture in the episode "The Itis", though this may have merely been part of an elaborate scheme to lower property values in the area so that he could purchase the nearby park and "develop" it. Along with this, he owns a fast food restaurant called "McWuncler", a parody of McDonald's as seen in the episode "Return of the King". He also has a sweatshop which is run by 12-year-old Indonesian girls as Huey reveals and Ed confirms in "The Block is Hot", demonstrating his ruthless manner. It appears that Wuncler's pettiness and self-severing nature knows no bounds, as in the episode "The Red Ball," he admits to orchestrating an elaborate hoax in order to emotionally traumatize Huey into never playing kick-ball again, by convincing Huey that he was responsible for giving a young girl a "...permanent, severe limp..." during a friendly kick-ball game, simply to make sure Huey would never challenge Wuncler's own undefeated kick-ball team in future competition. In the season 3 finale, "It's Goin' Down," Ed masterminds a false terrorist attack in Woodcrest, with the intention of making the lone victim (an overweight security guard) a national martyr and cultural icon, and then exploit his likeness for profit including a film that would star Jack Black. The plot is foiled by Huey and a government agent named Jack Flowers, but Ed avoids arrest thanks to the intervention of President Barack Obama (who called up Jack Flowers). In the final minutes of the episode, an angry Flowers takes Ed's grandson hostage, and he responds by smiling and saying "What are you waiting for? Shoot him!"
- Ed Wuncler Jr. (voiced by Sam McMurray) - Ed Wuncler Jr. is the son of Ed Wuncler Sr., immoral like his father with an apparent code of conduct akin to the mafia as he is not above committing acts of violence. Wuncler Jr. first appears in Season 4 to seemingly help Robert with his money trouble in "Good Times", only to have the Freeman family in even worse conditions and in debt to him. Soon after, Wuncler Jr. has the Freemans and other people indebted to him work in the his Freedomland amusement park as slaves. But Huey stages a revolt and the amusement park closes soon after.
- Ed Wuncler III (voiced by Charlie Murphy) - Ed Wuncler III is the grandson of Ed Wuncler Sr. and the son of Ed Wuncler Jr. Ed Wuncler III is a drunken, psychopathic, trigger-happy ex-special forces soldier freshly discharged from active duty in Iraq. His character could be seen as a parody of a young George W. Bush, painted in broad strokes — a figure destined to be president on the strength of his family's wealth and power, despite his sub-average intelligence (as referenced at the end of "The Garden Party", where his grandfather says, "In 30 years, that boy will be President of the United States... and he'll still be a fucking idiot!"). His personality and physical appearance are strikingly similar to rapper Eminem (especially his Slim Shady persona). He reveals that while in Iraq, he defecated in his pants out of fear so many times that the smell compromised his unit's position; he was not allowed to go on patrol as a result. Ed's bling includes a large medallion in the shape of the letter W, and he frequently wears a bulletproof vest. Although he is set to inherit an enormous fortune, he insists upon living a life of poorly executed crime, usually on behalf of his grandfather's business interests or as personal favors to Riley Freeman. He seems to have trouble distinguishing targets; as he has repeatedly kidnapped or attempted to murder the wrong person. Ed III and his friend, Gin Rummy, get away with their misguided and comically inept criminal antics because Ed Wuncler Sr. has the police and everyone else in the city on his payroll, and because his status as a member of the U. S. Armed Forces confers the public image of a hero no matter how immoral his actions may be, while Gin Rummy often argues that their escapes are the result of his being a master planner. For example, the pair go unpunished when staging a poorly executed bank robbery; Ed and Rummy are seen as heroes when they rob a convenience store owned by a person of "terrorist descent" after an unexpected shootout ensues; in attempting to kidnap Oprah Winfrey, they mistakenly abduct Maya Angelou, then Bill Cosby instead. Ed's signature line is "'The fuck y'all looking at?"
- Gin Rummy (voiced by Samuel L. Jackson) - Gin Rummy is a former special forces soldier and Ed Wuncler III's best friend. The character is apparently intended as a parody of Donald Rumsfeld by similarities in name, appearance, and use of actual quotes. His last name, "Rummy," matches the nickname given to Rumsfeld that was often spoken by President George W. Bush. Even though he is shown to be more intelligent than his best friend, he shares the same homicidal tendencies. His name is also a reference to the card game Gin rummy. When someone challenges his poor criminal planning, claiming they only get away because no one comes after them, he defends himself by claiming just because they do not know no one comes after them does not mean there is not anyone coming after them, asserting that "the absence of evidence is not the evidence of absence" (parodying the claims of Bush and Rumsfeld regarding Saddam Hussein's supposed weapons of mass destruction in Iraq) in reference to the assertion that no one ever comes after them or by insisting that he could not plan for "unknown unknowns". It also seems he is a way for the writers to complain about modern technology because in every episode he appears in he complains about it from the Bluetooth head set to the iPhone. Gin Rummy considers himself a patriot and will do whatever it takes to bring the "Fugitives of Justice" their due. Though never implied, he is probably individually wealthy, unlike Ed who is an inheritor. He first appears in the episode "A Date With The Health Inspector". His style of speaking often parodies Samuel L. Jackson's character Jules Winnfield from Pulp Fiction. In many episodes Rummy drives a black Cadillac Escalade.
- Otis Jenkins (voiced by series producer Carl Jones) - Otis Jenkins is a once-famous rapper named Thugnificent and Riley's most recent idol. Thugnificent hails from the fictional town of Terra-Belle, Georgia. He is loud-mouthed and sports afro puffs similar to those worn by the rapper Ludacris. His narcissism is unmatched, epitomized by the ubiquitous statues of himself, designed to mirror Ancient Greek gods in their style and pose, that adorn his white-and-gold mansion, as well as by a painting depicting himself standing above Martin Luther King, Jr., Malcolm X, Tupac Shakur and The Notorious B.I.G.. Soon after moving into the neighborhood, he begins a rivalry with Robert and later initiates Riley into his entourage, the "Lethal Interjection Crew," consisting of himself, fellow rappers Macktastic and Flonominal, whom he met through his record label, and "other niggas [he's] known his whole life". Despite his less-than-attractive traits, Thugnificent does attempt to be a good neighbor by asking for permission to throw his loud parties and encouraging face-to-face communication within the neighborhood, and is fairly friendly with most other neighborhood citizens. In the episode "The Fried Chicken Flu" he is even seen saving the family from Uncle Ruckus and Mrs. Von Hueson, after Robert kicked him out of the house. In "Bitches To Rags" it is revealed that Thugnificent has a bachelor's degree in Communications. "Bitches To Rags" also reveals that Thugnificent's record sales and popularity have been in sharp decline; by the end of the episode his home is foreclosed and his belongings auctioned to pay his debts. Relinquishing his stage name, Otis thus begins a new career as a delivery man and cuts his hair (all the while hoping for a reality show to save him from "real work"). His catchphrase is "Eat a Dick!!". He is a marijuana aficionado; being a firm critic of the Pharmaceutical industry, he admits he doesn't consume any medications over the counter or prescribed.
- Leonard (voiced by DeRay Davis) is Thugnificent's dim yet well-meaning friend and member of Thugnificent's Lethal Interjection Crew. Although Leonard was treated as a second-class member of the Lethal Interjection Crew—mostly due to his penchant for being socially awkward—he is the only member of the crew to stick with Thugnificent when he lost all of his money. While he is shown to be slow and a bit of a buffoon (Believing that Buffalo Wings are made from Buffalo), he is also shown to be more thoughtful, generous and loyal than most characters on the show. In the third season he is almost always shown in his Wendy's uniform, the job he took after Lethal Interjection disbanded.
Real life characters
- Martin Luther King, Jr. (voiced by Kevin Michael Richardson) - In this show, Martin Luther King, Jr. did not die from being shot at. Instead, he ended up in a coma that lasted for years. He came out of his coma in "Return of the King" following the events of 9/11.
- Sway Calloway (voiced by himself) - Sway is the MTV News reporter who first appears in "The Story of Gangstalicious" narrating the documentary "Gangstalicious: Resurrection" and then the breaking news. He last appears in "The Story of Thugnificent" narrating the documentary "Thugnificent: Rags to Bitches." He also appears in shinin' reporting Riley's chain getting stolen.
- Bill Cosby (voiced by Kevin Michael Richardson) - Bill Cosby is played as a barely intelligible cynic who complains endlessly about the poor manners of young people. Ed and Rummy kidnap him in "Let's Nab Oprah," but return him almost immediately as they find him too annoying.
- Xzibit (voiced by himself) - Xzibit pimps the Freemans' car Dorothy as a result of one of Riley's scams, and makes a short appearance in the second season when Granddad asks him to assist with a diss rap.
- Ghostface Killah (voiced by himself) - Ghostface Killah appears to Huey as a ghost (despite not being actually dead) and advises him when Tom Dubois is possessed by Stinkmeaner's spirit.
- Lamilton Taeshawn (voiced by Bobb'e J. Thompson) - Lamilton Taeshawn is based on Latarian Milton, the 7 year old who stole his grandmother's car and went for a joyride, quotes such as "I like to do bad things" and "my friend who smokes wit cigarettes" are said by both Lamilton and Latarian. A friend of Riley's but, he soon realizes that Lamilton's intentions were evil. He (like his real-life counterpart) steals his grandmother's car and goes on a joyride with Riley, and convinces him to engage in all types of misconduct (spraying a combination of hot sauce and urine at people, dropping a life-sized dummy of a person from an overpass to cause a massive car pileup, etc.) until his attempts to rob Mrs. Van Hausen's house result in him killing a dog, at which point he is apprehended. Lamilton gets out of the system and, believing that Riley is the one who told on him (it was actually his former therapist who was stalking him under the suspicion that he was still dangerous), hunts him down and tries to kill him. After the ensuing fight, he falls off a roof and survives, but is attacked by the therapist.
- The Booty Warrior - The Booty Warrior is a homosexual prison inmate who is based on real-life convicted serial rapist Fleece Johnson in appearance, voice, and personality, though here The Booty Warrior's mannerisms (and obsession with anally raping men) are more of a caricature of Johnson's than anything else. In "A Date With the Booty Warrior", it is revealed that The Booty Warrior was convicted due to raping Chris Hansen. During a program where troubled schoolchildren are sent to prison where they will learn what happens there at which Tom was chaperoning, Booty Warrior developed a crush on Tom and holds him hostage with a shank he stole from Tom (who took it from Riley prior to the field trip) in an attempt to rape him, and a riot ensues. The Booty Warrior stalks Tom in his attempt to anally violate him, but loses when he steps on wet soap.
- Winston Jerome - Winston Jerome is a superstar playwright, screenwriter, actor and cult leader. He appears in the episode "Pause" where it is revealed that Winston founded his theatrical cult for the purpose of having sex with men. Robert auditioned to be the leading man in one of his plays. His character, and more specifically, his success as an actor and scriptwriter, is a spoof of Tyler Perry.
- Joe Petto (voiced by Fred Willard) - Riley's school teacher who in a state of confusion called him "nigga" causing an uproar. Petto is confused because he had assumed that saying "nigga" was different from "nigger". Petto fervently states that Riley said the word first, and says it so frequently he does not even notice. Petto is based on the real-life teacher Paul Dawson who called his student Keysean Chavers "nigga" during a confrontation in class. Petto's confusion on the words are exclusively based on Dawson.
- George W. Bush - 43rd President of the United States.
- Wedgie Rudlin (voiced by Donald Faison) - Wedgie Rudlin is President of entertainment for BET, and a simpering yes-man to his superiors. An obvious parody of actual BET President of entertainment (and executive producer for the Boondocks) Reginald Hudlin.
- Kardashia Kardashian (voiced by Grey DeLisle) - Kardashia is a parody of the Kardashian sisters of Khloe, Kim, and Kourtney. Like them, she is a Caucasian reality TV star with butt implants, which explode during one date with Robert. She dies alone and the pilot for her reality show was never pitched.
- Siri (voiced by Grey DeLisle) - An app that Granddad becomes attached to and the main antagonist of "I Dream of Siri". But, when he said that he loves her, Siri becomes obsessed. Going haywire, she hacks Robert's new Android and at the wedding, she sends fake pictures of Robert being a terrorist to al-Qaeda. A drone comes to the Freeman house and destroys Siri. Granddad's complaint made it to Apple. He is also removed from the president's kill list and also received a free iPad, as shown in the epilogue notice.
- The White Shadow (voiced by John C. McGinley) - The White Shadow is a white, blond secret agent whose responsibility is spying on Huey for his radical actions. An enigmatic individual claiming to be sent by the apparent "powers that be" to spy on Huey from monitoring his communications to personal conversations. It is not proven as to whether or not he is a real agent or simply a figment of Huey's imagination due to his ever increasing paranoia; given the fact that he appears and disappears so easily and no one else has yet to see him. Though he seems as a sinister individual, he usually appears to provide insight or warn Huey. Huey is the one who dubs him "The White Shadow."
- Gangstalicious (voiced by Mos Def) - Gangstalicious is one of Riley's favorite rappers. Gangstalicious features in "The Story of Gangstalicious", "The Story of Gangstalicious Part 2", and "Thank You for Not Snitching" and makes a cameo appearance in "It's a Black President, Huey Freeman." He is responsible for the hit single "Thuggin' Luv" heard in the show ( which is heard in many episodes), as well as "Homies Over Hoes". Inspired as a child by Ice Cube, he acted "like a killer" so people would like him. This behavior carried over into his adult life, and he's been living a lie ever since. He is a closet homosexual and goes to great lengths to keep this secret from the public. He was formerly involved in a secret homosexual affair with a gangster named Lincoln who attempts to kill Gangstalicious for betraying their love while on tour, and at some point assaulted a record label executive and rapped about it on TRL only to be arrested later. He was also involved in a relationship with a hip-hop video vixen named Jessica Ethelberg, who later wrote a book revealing he was gay (despite the fact that there were already countless obvious clues to the fact beforehand). His real name is Frederick.
- Macktastic (voiced by Snoop Dogg) - Macktastic is a rapper and member of Thugnificent's Lethal Interjection crew. Despite his stereotypical gangsta attitude, he is shown to be quite articulate in his speech at times (slightly similar to his voice actor), and is a man of few words. His appearance resembles that of Taboo of The Black Eyed Peas. After the fall-out of Lethal Interjection, Thugnificent mentions that Mack went back to pimpin'.
- Flonominal (voiced by Busta Rhymes) - Derrick Cornish is a rapper under the name Flonominal and member of Thugnificent's Lethal Interjection crew. His vocabulary seems to be quite limited, and uses hip-hop slang frequently at the end of, even in between his sentences, and if he cannot think of anything else to say such as "Word!" and "Nah mean?" (phrases commonly used by the rapper Ghostface Killah of the Wu-Tang Clan, who plays a role in "Stinkmeaner Strikes Back"). Although he puts on a hard-man, gangsta facade and is as loud as Thugnificent at times, he is shown to be soft and sensitive, as seen as when his mother called him and scolded him about the controversy caused the Lethal Interjection label and the constant attacks on the elderly by Thugnificent's rivalry with Robert Freeman (Granddad), and when Butch Magnus Milosevic hit him on the leg with a baseball bat, after demanding Riley's chain back. He resigns from the Lethal Interjection in "Bitches to Rags" when Thugnificent is unable to pay for the house and when Thugnificent gets him fired from a job as an office worker.
- A Pimp Named Slickback (voiced by Katt Williams) - A Pimp Named Slickback is a pimp who gets easily irritated when someone calls him "Slickback" for short, demanding to be addressed by his complete self-professed name: "It's like 'A Tribe Called Quest' — you say the whole thing." He first appeared in "Guess Hoe's Coming to Dinner" when Granddad began dating his prostitute, Cristal. He made a cameo appearance in "Return of the King" but had no speaking lines. He appears in the season 2 episode "Tom, Sarah and Usher", in the episode where Tom believes Sarah is having an affair with singer Usher, attempting to teach Tom to gain the respect of his wife through violence and intimidation. The character is modeled after Katt Williams' character of "Money Mike" in Friday After Next. He also drives a purple BMW which matches his purple suit. He also appears in "The Story of Gangstalicious Part 2" where he is brought in by Granddad to talk to Riley about sex and dissuade him from homosexuality.
- Colonel H. Stinkmeaner (voiced by Cedric Yarbrough) is a blind old black man whose appearance resembles Dr. Badvibes from C.O.P.S.. As Huey states, Stinkmeaner has acted like an ornery old man for his entire life as and saw his Cancer-induced blindess at age 15 as good thing since he hated everything and everyone he saw. Though expected to die within three years, the doctors believed that Stinkmeaner's "Love of Hatred" kept him alive as he dedicated the rest of his life to making everyone's lives a living hell. After beating Robert in a fight in the mall parking lot, Huey mistakes Stinkmeaner for a blind swordsman (specifically Zatoichi) and has his Granddad train to fight Stinkmeaner. But by the time Huey realizes Stinkmeaner is a regular old man, having had the match legally sanctioned prior at the last second to ensure no prosecution, the fight ended with Robert unintentionally killing Stinkmeaner. Ending up in Hell soon after, Stinkmeaner trains in martial arts before the events of "Stinkmeaner Strikes Back" where the Devil sends him back to Earth to spread ignorance and chaos among black people. Once back on Earth, Stinkmeaner possess Tom Dubois to take revenge upon Robert before being exorcised when tricked by Huey into finding common ground with Uncle Ruckus. In the season 3 episode "Stinkmeaner III: The Hateocracy," serving as its narrator, Stinkmeaner is revealed to have belonged to a crew of violent, elderly hoodlums known as the "Hateocracy." Once notified of Stinkmeaner's death, the surviving members of the Hateocracy, a trio of skilled martial artists named Lord Rufus Crabmiser, Lady Esmerelda Gripenasty, and Mister George Pistofferson, reunite to attack the Freeman family as it gave them an excuse to ruin someone's life. Luckily, as Crabmiser murdered Bushido Brown during the attack, the Hateocracy are arrested by the police shortly. In the season 4 episode "Stinkmeaner: Begun the Clone War Has", it is revealed that Stinkmeaner enlisted in a cloning project prior to his death and left instructions for his clone, who is genetically enhanced, to continue antagonizing Robert. Eventually, after Robert newly descended to his level, the Stinkmeaner clone renounces the vendetta but still harasses the Freeman family.
- Reverend Rollo Goodlove (voiced by Cee-Lo Green) - Reverend Rollo Goodlove is an African-American left-wing activist whose activism seems more to get him media exposure than to show his opinion on the issue. He originally appeared in the Boondocks episode "The S-Word", as a supporter of the Freemans after Mr. Petto used a racial "slur" on Riley. He then turned it into a political debate between himself and Ann Coulter (which was carefully orchestrated) giving him more media exposure. His protest was overshadowed (forcefully with rifles) by elderly women protested for the right to own guns. Granddad was certain he will receive lots of money for the incident. He also helped Huey in a hunger strike in an attempt to pull BET off the air, but Rollo was offered a TV sitcom to be aired on BET, which led to him no longer aiding Huey's strike. His character is loosely based on Rev. Al Sharpton and Jesse Jackson.
- Cynthia "Cindy/Ceemer/Fearsome" McPhearson (voiced by Tara Strong) - Cynthia is a girl who originally appeared as a recurring character in the comic strip as a girl in Huey's class who is oblivious to racial issues. She enjoys rap music, especially Snoop Dogg. In the TV series, she appears as an extremely-talented junior basketball player for her team, is well-versed (yet overblown) in AAVE, and matches Riley in cockiness. Riley soon resorts to insulting her mother and the problems related to her in Cindy's life to put her off her game, which leads to her crying and running off the court. She appears in the episode "Ballin'" and "The Story of Gangstalicious Part 2", in Season 2 and in Season 3 in the episode "The Red Ball" as part of Huey's kickball team, although she doesn't speak. She has a bigger role in the Season 3 episode "The Fundraiser" as one of Riley's partners in his chocolate enterprise.
- Bushido Brown (voiced by Cedric Yarbrough in the first appearance, Michael Jai White in the second appearance) - Bushiso Brown is a kung-fu bodyguard hired by Oprah. For a while on the show he is the best martial artist whose skills greatly surpass Huey Freeman. He appeared in the season one episode "Let's Nab Oprah" and the season two episode "Attack of the Killer Kung-Fu Wolf Bitch". He is killed in the season three episode "Stinkmeaner 3: The Hateocracy" after being decapitated in a fight with three elderly martial artists the "Hateocracy" (who were associated with Colonel H. Stinkmeaner) when they were out to kill Robert using a flying guillotine at the time when he was protecting them. Before his demise, he is revealed to be an arrogant jerk who overcharges his clients for his services. After Bushido Brown's death, the Hateocracy members are arrested by the police for the murder of Bushido Brown. Bushido Brown's character is heavily influenced by the character Black Belt Jones from Black Belt Jones and William from Enter the Dragon (both played by martial artist Jim Kelly), as well as Michael Jai White's own character parody "Black Dynamite" from the film Black Dynamite.
- Mrs. Van Heusen (voiced by Marion Ross) - Mrs. Van Heusen is a right-wing elderly woman who is head of the local neighborhood watch, and Second Amendment Sisters. When Ed the 3rd and Gin Rummy are engaging in their local crime spree, she tries militarizing the neighborhood watch after the Freemans. During the Fried Chicken Flu, she organizes another militia to try and take the Freeman's supplies.
- Deborah LeVil (voiced by Debra Wilson) - Deborah LeVil who is the fictional head of BET (Black EVIL Television). Deborah LeVil is a Psychotically Evil Woman dedicated to the Network's Goal: The Destruction of Black People. She has been shown to murder her employees when they do not meet her insidious standards. As she States, "It's not enough that the Shows are bad. They have to be EVIL as Well!" She is mostly portrayed as a female version of Dr. Evil from the Austin Powers film series.
- "The Boondocks: Exclusive Character Profile - Uncle Ruckus". IGN. Retrieved 2010-08-10.
- "The Boondocks: Beware Colonel Stinkmeaner". IGN. Retrieved 2010-07-26.