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Riley Freeman "Young Reezy" is the deuteragonist of The Adult Swim sitcom The Boondocks. He is also the younger brother of Huey Freeman. He a lot of the times is a sukup to thugnificant a rapper in the series and argues with his brother Huey Freeman. Although he helps his brother and his grandad Robert Freeman when he needs to help them. Despite being an antagonist at to times he can do some good things with his brother and grandad.
Although he is a male, he was voiced by Regina King, who also voiced his brother Huey.
Riley is a highly impressionable third grader. He embraces the stereotypical "gangsta" lifestyle, doing his best to promote the urban culture in the contrasting suburb of Woodcrest. Influenced by the mass media via rap music and television, he frequently uses poor grammar, and tends to defend his idols even when his imitations go against common sense and righteousness. One example is his support of R. Kelly in "The Trial of R. Kelly", despite overwhelming evidence proving Kelly's guilt, Riley believes he should not have to miss out on his next album because of Kelly going to jail. This is further shown in "The Story of Gangstalicious Part 2" where he dresses in effeminate clothing only because Gangstalicious created the style. He also refused to believe that the rapper was gay despite the obvious clues to the contrary. In an effort to further emulate the lifestyle he praises, he collects airsoft weapons and tags houses, as demonstrated in "The Garden Party" and "Riley Wuz Here".
Riley seems to have a fair amount of criminal aptitude, as is demonstrated when he helped plan the kidnapping of Oprah Winfrey, and further demonstrated by his criticisms of Ed Wuncler III and Gin Rummy for their lack of criminal know-how in "Let's Nab Oprah".
Despite his pretensions to the contrary, Riley is nowhere near stupid. In several instances he is shown to be very resourceful and pragmatic, and "beats" Tom, a district attorney, in an argument over R. Kelly's confinement and trial. Perhaps due to idolizing the gangsta rap lifestyle he seems to have a level of street smarts possibly as great as his brother, often able to manipulate situations through lying and reverse psychology. Which he refers to as getting into someone's "mental mind". Riley is quite brash and could often get into situations without considering first, also making him a trouble maker. He is also quite rebellious and does not listen to anyone, especially Huey and Granddad. He is brutally honest to the point of being very rude.
Riley overestimates himself extremely. Believing himself to be phenomenally skilled in basketball but in reality having no such talent. The same was seen in kickball.
Riley seems to take great pleasure in poking fun at other people, sometimes to the point where Huey or Robert have to hit him to make him stop, although such disciplinary actions usually have no effect on his behavior. He also holds grudges; he has a grudge, for example, against Santa Claus for not getting him what he wanted for Christmas back when he lived in the ghetto, and went so far as to stalk and assault Mall Santa's with airsoft guns ("A Huey Freeman Christmas").
Riley's excessive interest in the "thug" lifestyle has made him into something of a misogynist. He claims that all women are "hoes", pointing to the custom that a man should pay for his girlfriend's dinner during a date - despite, as Huey points out, that men are actually paying the restaurant, not the woman - a contradiction that Riley does not recognize. He also tends to use "bitches" as a general term for women.
Unlike other characters in the series, Riley has a notorious tendency to drop the N-word on almost everyone, regardless of their skin color. His fight with Butch Magnus and interview with Werner Herzog are two examples.
Riley sometimes overestimates his own combat abilities, such as when he tried to fight his brother in "Let's Nab Oprah". His thuggish fighting style, both with weapons and hand-to-hand, has failed several times against the precision of Huey's martial arts ability. He does seem to have some talent with airsoft guns, as he fought Huey to a tie in season two. It can be shown that he has a strong amount of endurance and determination, seen when he receives many harsh attacks from his opponents but is able to continue fighting, seemingly ignoring his injuries to a certain limit.
All in all, even though his opponents are far more experienced than him (either by size or martial arts), in all fairness however, his fighting skills seems to have improved, ever since his fight with Lamilton Taeshawn. As of season 4 he has shown to be acrobatic, by somersaulting in the air (with great precision) to turn one of the lights off. It is currently unknown if his acrobatic skills are the result of one of his maneuvers to hide from unwanted neighbors/people or if he learned some martial arts from Huey.
Out of the three members of the Freeman Family, Riley is considered the least experienced fighter.