Riley Freeman

Boondocks character
name = Riley Freeman
picture =
relatives = Huey Freeman (brother) Robert Freeman (grandfather) Cookie Freeman (great aunt)
voiceactor = Regina King
firstepisode = "The Garden Party"

Riley Freeman is a fictional character from the comic strip "The Boondocks" and its TV series adaptation. He often refers to himself as "Riley Escobar," and 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 a foil of his brother's more politically and socially-driven mindset.

Riley, who grew up on the south side of Chicago, was moved along with his brother to the peaceful, predominately white suburb of Woodcrest by their granddad. In some episodes, he and Huey would have a single storyline. In others, the two would each have their own in a single episode. Riley, like Huey, is voiced by Regina King.

Personality

Riley is a highly impressionable third-grader who tightly embraces the stereotypical "gangsta" lifestyle, doing his best to promote the urban culture in the contrasting suburb of Woodcrest. Influenced by the mass media by way of 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 shouldn't 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 (refusing to believe that the rapper was gay despite the obvious signs). 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 Winfrey, and further demonstrated by his criticisms of Ed Wuncler III and Gin Rummy for their lack of criminal know-how ("Let's Nab Oprah"). Despite his pretensions to the contrary, Riley is not stupid: he can in fact 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 doesn't listen to anyone, especially Huey and Grandad. He is brutally honest to the point of being very rude.

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 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 (he was more highly armed, though). It can be shown that he has a strong amount of endurance and determination, 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 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 (which is ironic considering that his voice actor is a woman). 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.

Riley is somewhat cynical. In "The Story Of Catcher Freeman", he recognizes that the stories of his Granddad usually are made-up: this can mean that he is, like his brother, a realist. He can keep a cool head, even under pressure: when both he and his idol Gangstalicious are under heavy gunfire, Riley remains stable while the supposedly hardcore Gangstalicious loses his composure, causing Riley to opine that Gangstalicious is a fraud, lamenting, "It's like going to heaven and finding God smoking crack."

Despite these less than admirable characteristics Riley is precociously clever, especially when required to think quickly or talk his way out of trouble. Usually he's able to get what he wants by manipulating people or disadvantageous events, like he did in "Let's Nab Oprah" - first with his Granddad, then when he saw Huey at the studios. 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.

Relationships

Huey Freeman

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. In "...Or Die Trying" Riley doesn't have any problem at abandoning his brother to his fate, but in other episodes he seems to trust him. Despite all this, Riley often insults his brother with the repeated phrase "Nigga, you gay.", usually after receiving a hug (although he just distanced himself from Huey while speaking those words in the episode "...Or Die Trying")

= Robert Freeman =

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.

Ed Wuncler III and Gin Rummy

Riley hangs out with them and refers to them as his "niggas" 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 tend to use him for their own personal gain, such as stealing his Granddad's car with knowledge that Riley won't reveal they 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 when he needs additional muscle, such as when he tries to get his Lethal Interjection chain back from Butch Magnus (Bitch Magnus Malosabitch) or when he and Huey need to seek out the X-box Killer.

Dubois Family

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 in prison. He also mocks Sarah's cooking by comparing her peach cobbler to vomit with peas in it ("The Itis").