"You wanna be in this business, you got to pay the cost to doing business, and when the cost gets too high, you get out of business."Riley Freeman

Riley Freeman

Riley 4


Rilefy Freeman


Born July 15 2007
Gender Male
Status Alive
Age 10
Location Woodcrest
Relatives Huey Freeman Robert Freeman
First Appearance The Garden Party
First Mentioned The Garden Party
Episode Count 54
Voiced By Regina King

Riley Freeman is the deuteragonist of The BoondocksHe often refers to himself as "Riley Escobar," and in season two, three, and four of the TV series, he also refers to himself as "Young Reezy." He is Huey's younger brother. He aspires to be like the rap artists and the gangsters that he admires.

Riley, who grew up on the south side of Chicago, was moved along with his brother to the peaceful, predominately white suburb of Woodcrest in Baltimore, Maryland by their granddad Robert Freeman. In some episodes, Riley and Huey would have a single storyline and in others, the two would each have their own in a single episode. Riley, like Huey, is voiced by Regina King. It is strongly suggested that Huey and Riley's birth parents are deceased. This is, in part, based on Robert's dialog from the first episode stating that he spent the boys' "inheritance" on their new house in Woodcrest. In "Riley Wuz Here", a later episode in season one, his parents being deceased is further hinted at when Riley spray-paints the Freeman house with a picture of his parents after his art teacher suggests that he "...paint someone you love. Maybe someone who's not with us anymore.".

History and Personality

Riley Freeman is an impressionable third grader who embraces the stereotypical "gangsta" lifestyle and lives his life like his idol rappers. Influenced by 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 R Kelly's guilt, Riley believes he should not have to miss out on his next album. This is further shown in "The Story of Gangstalicious Part 2" where he dresses in effeminate clothing because Gangstalicious created the style. 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 is 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 simpleminded: 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". Despite his crude thuggish lifestyle motivated by greed or laziness, on rare occasion he has displayed acts of compassion (giving $100 to a panhandler he previously ignored and spat at, showing his basketball teammates how to shoot as opposed to being a ball hog).

Riley is quite brash and abrasive and often gets into undesirable situations without considering the consequences. He is rebellious and does not listen to anyone, especially Huey and Robert. He is brutally honest to the point of being very rude.

Despite the fact that Huey is forced to act as the voice of reason towards Riley's antics, usually without any success, Riley himself does become the voice of reason for his own friends, such as Thugnificent or Ed and Rummy.

When forced to fight, he resorts to a crude and thuggish form of attack, in contrast to his brother's carefully calculated attacks. His method is simply to continue attacking, usually with concealed BB guns, and random objects, such as vases, or lamps. Riley sometimes overestimates his own 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. However, in "Smokin' With Cigarettes," he single-handely won his fight against Lamilton, resulting in his first victory. His street-fighting style has improved to a certain degree in season 3. He does seem to have some talent with airsoft guns, as he fought Huey to a tie in season two. He has a strong amount of endurance and determination and given his previous beatings by his grandfather seems to have a high threshold for pain.

Riley has in spite of himself, shown a great degree of intelligence from time to time. It's has been shown he has a great understanding of the Media world and music industry. This was shown when he tried to advice Thugnificent against starting rap war with much Younger aspiring rap star Sgt. Gudder, Thus humiliating himself..

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'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 adknowledge. 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
 and taking advantage of situations, 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. He also tends to use "bitches" as a general term for women, like Thugnificent does. 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 out God smokes crack." As of Season One, Riley still wets the bed. In season four, Riley who is also mad about how in debt he and his family are,  tries to help his granddad with getting a job.


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 is not around, Huey usually will not hesitate to set Riley straight himself. In "...Or Die Trying" Riley does
not 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"). In the Season 3 finale however, Riley offers Huey a hug near the end without insulting him but admiring Huey when they saw him on the television instead.

Robert Freeman

Robert Freeman is Riley's paternal grandfather. 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 does not influence or change his actions in any significant way. Riley seems to not understand his grandpa's rules and gets whipped when he makes a bad choice. They are shown to be close at times and agree on things in season two. In season three, the two are seen to have "father and son" moments, such as when they go out to try the new fried chicken in The Fried Chicken Flu. They also attempt to go to the inauguration of Barack Obama in "It's a Black President Huey Freeman" In the fourth season Riley is upset about how granddad throws money away to girls and not try to help with their financial problems.

Ed Wuncler lll and Gin Rummy

Riley hangs out with them and refers to them as his friends. 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 suburb. Riley sometimes accompanies them on their various misdeeds, and is not 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 Riley for their own personal gain, such as stealing his Granddad's car with knowledge that Riley will not 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 or when he and Huey need to seek out the Xbox Killer.

Cindy McPhearson

Cindy could be considered the white female counterpart of Riley and is initially an antagonist to Riley as seen in the season two episode Ballin'. Cindy and Riley were initially rivals on different basketball teams in the local league, but in The Story of Gangstalicious Part 2, Granddad invites her over to play with him, signifying a small amount of
friendship. In the Season 3 episode The Fundraiser, Cindy became a business partner of Riley's and helped him, Jazmine, and Phil, a seldom used stereotypical ignorant kid, sell large amounts of chocolate bars in order to make money. She becomes the last remaining partner of Riley, being the only one not to bail out of the organization.