Colonel H. Stinkmeaner

The following is a partial list of characters who have appeared in the animated television series The Boondocks.

Huey Freeman (voiced by Regina King) is a young leftist radical Black revolutionary and retired domestic terrorist. He is a practicing s 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.

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