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The Boondocks character
Riley Freeman
Gender	Male
Hair	Black cornrows (show) Short (strip)
Job	Student
Relatives	Huey Freeman (brother) Robert Freeman (grandfather) Cookie Freeman (aunt)
Interests	Art (especially graffiti) Guns Creating mischief Cooking Gangsta Rap Basketball
Voice actor	Regina King
Debut	"The Garden Party"

Riley Freeman is a fictional character from the TV series, The Boondocks, who also appears in a comic strip by the same name. In season two of the TV series, he has begun to refer to himself in some situations as "Young Reezy." He is Huey's eight-year old brother who aspires to be like the rap artists and the gangsters he admires. This obsession molds his personality into one that is extremely contradictory to that of his brother. Riley, like Huey, is voiced by Regina King. Riley, who grew up with his brother, on the south side of Chicago, was moved along with his brother to the peaceful, predominately white suburb of Woodcrest by their granddad.

Young Reezy is known as a young "gangsta" on the rise as the rap artists and the original gangsters commonly say. Highly influenced by the mass media by way of rap music and television, he frequently uses non-standard grammar in order to sound "gangsta". He tends to defend his idols even though it goes 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. In order to be like his idols, he collects airsoft weapons and tags houses, as demonstrated in The Garden Party and Riley Wuz Here. He also seems to be a fan of the movie Scarface in that he occasionally quotes lines from or alludes to the movie, and he has a white suit similar to the one worn by Tony Montana.

Riley seems to have a fair amount of criminal aptitude, as is demonstrated when he helped coordinate the kidnapping of Oprah, and further demonstrated by his criticisms of Ed Wuncler III and Gin Rummy for their lack of criminal know-how (Let's Nab Oprah).

Riley sometimes overestimates his own rather crude 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, failed against the precision of Huey's martial arts ability. However, it can be shown that he has a strong amount of endurance, seen when he receives many harsh attacks from his opponents (like Huey and Butch Magnus) but is able to continue fighting, seemingly ignoring his injuries to a certain limit.

Riley going after Santa with a golf club in A Huey Freeman Christmas.

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, though 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 Santas 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", rebuking 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.

Despite these less than admirable characteristics, Riley has occasionally shown the capacity to be precociously clever, especially when required to think quickly or talk his way out of trouble. He is also an extremely talented visual artist and had been using graffiti as his primary window for artistic gratification until the episode Riley Wuz Here during which he learns to paint selflessly and for the benefit of the viewer instead of personal glory. He still, however, admits that he hopes his artistic talent lets him "get paid." One might say it's the heavy influence of mass media, particularly modern-day rap culture, that inhibits his intellectual potential. Thus, Riley's characterization is McGruder's way of satirizing many youths today who have the potential to do so much but choose to waste it, and instead end up in trouble with the law or worse.

Huey and Riley tend to have a regular brotherly relationship despite their contradictory personalities. Due to the blunders Riley makes, Huey inevitably tries to teach him the error of his ways, but often to no avail. When their granddad isn't around, Huey usually will not hesitate to set Riley straight himself.

Riley constantly disrespects Robert. Robert mainly resorts to physical punishment to keep Riley in line, but Riley seems accustomed to this kind of disciplinary action to the point where it doesn't influence or change his actions in any significant way. They are shown to be close at times and agree on things in Season 2.

Riley hangs out with them because they're the closest thing to a gang that exists in Woodcrest. They have a great variety of real firearms and are free to commit any crime they wish since Ed's grandfather essentially owns the city. Riley sometimes accompanies them on their various misdeeds, and isn't afraid to point out when their crimes are poorly-planned or are only successful because of Ed's grandfather's status. However, Rummy dismisses Riley's reasoning and says they get away with crimes because he (Rummy) is a criminal mastermind. However, they usually use him for their own personal gain, such as stealing his Granddad's car with knowledge he won't reveal he did it, then when it was eventually returned, they stole his new bike, fitted with rims riding as they shouted: "Thank you for not snitching!...You stupid motherfucker!" Riley also contacts Ed and Rummy when he needs additional muscle, such as when he tries to get his Lethal Interjection chain back from Butch Magnus.

Riley likes to make fun of the Dubois family – especially Tom. He mocks Tom's unmanliness, breaks Jazmine's beliefs, and makes fun of Sarah's cooking. He outwits Tom, an attorney, in an argument about R. Kelly's trial and makes fun of Tom's fear of being anally raped. He also mocks Sarah's cooking by comparing her peach cobbler to vomit with peas in it (The Itis).