Riley Freeman
Encyclopedia
Riley Freeman is a fictional character from the syndicated
Print syndication
Print syndication distributes news articles, columns, comic strips and other features to newspapers, magazines and websites. They offer reprint rights and grant permissions to other parties for republishing content of which they own/represent copyrights....

 comic strip
Comic strip
A comic strip is a sequence of drawings arranged in interrelated panels to display brief humor or form a narrative, often serialized, with text in balloons and captions....

 The Boondocks written by Aaron McGruder
Aaron McGruder
Aaron McGruder is an American cartoonist best known for writing and drawing The Boondocks, a Universal Press Syndicate comic strip about two young African American brothers from inner-city Chicago now living with their grandfather in a sedate suburb, as well as being the creator and executive...

 and its TV series
The Boondocks (TV series)
The Boondocks is an American animated series created by Aaron McGruder on Cartoon Network's late night programing block, Adult Swim, based on McGruder's comic strip of the same name...

 adaptation. He often refers to himself as "Riley Escobar," and in season two of the TV series, he also refers to himself as "Young Reezy." He is Huey's
Huey Freeman
Huey Freeman is a fictional character of The Boondocks syndicated comic strip written by Aaron McGruder, as well as the main character and recurrent principal narrator of the animated TV series of the same name...

 eight-year old brother who aspires to be like the rap artists and the gangsters that he admires.

Riley, who grew up on the south side of Chicago
Chicago
Chicago is the largest city in the US state of Illinois. With nearly 2.7 million residents, it is the most populous city in the Midwestern United States and the third most populous in the US, after New York City and Los Angeles...

, was moved along with his brother to the peaceful, predominately white suburb of Woodcrest by their granddad
Robert Jebediah Freeman
Robert Jebediah "Granddad" Freeman is a fictional character in the animated television show The Boondocks, as well as a regular character in a comic strip of the same name. He lives in the suburb of Woodcrest with his two grandsons, Huey Freeman and Riley 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
Regina King
Regina King is an American film and television actress. She is well known for her role as Mary Jenkins's studious daughter, Brenda Jenkins, on the 1980s sitcom, 227, and for her critically acclaimed supporting role in the feature film Jerry Maguire...

. 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.

Personality

Riley is a highly impressionable third grader who tightly embraces the stereotypical "gangsta" lifestyle, who lives his life by living like his idol rappers.
Also 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
R. Kelly
Robert Sylvester Kelly , better known by his stage name R. Kelly, is an American singer-songwriter and record producer. A native of Chicago, Kelly began performing during the late 1980s and debuted in 1992 with the group Public Announcement. In 1993, Kelly went solo with the album 12 Play...

 in "The Trial of R. Kelly
The Trial of R. Kelly
"The Trial of R. Kelly" is the second episode of the Adult Swim animated television series The Boondocks. It originally aired on November 13, 2005.-Plot:...

": 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
The Story of Gangstalicious Part 2
"The Story of Gangstalicious 2" is an episode of the Adult Swim animated television series The Boondocks. The episode aired on February 4, 2008 and is the last episode from the second season to air in the United States.-Plot:...

" 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
Airsoft
Airsoft is a sport in which participants shoot round non-metallic pellets launched via replica firearms.Gameplay varies in style and composition but often range from short-term skirmishes, organized scenarios, military simulations, historical reenactments, to competition target shooting events...

 weapons and tags houses, as demonstrated in "The Garden Party
The Garden Party
"The Garden Party" is the pilot episode of the Adult Swim animated series The Boondocks, although the production number, 103, suggests it was the third episode produced...

" and "Riley Wuz Here
Riley Wuz Here
"Riley Wuz Here" is the twelfth episode of the Adult Swim animated television series, The Boondocks. It originally aired on February 19, 2006.- Plot :Riley opens the episode by piecing the side of a neighbor's house...

". He also seems to be a fan of the movie Scarface
Scarface (1983 film)
Scarface is a 1983 American epic crime drama movie directed by Brian De Palma, written by Oliver Stone, produced by Martin Bregman and starring Al Pacino as Tony Montana...

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
Tony Montana
Antonio Raimundo "Tony" Montana is a fictional character from the 1983 film Scarface. He is portrayed by Al Pacino in the movie, and is voiced by André Sogliuzzo in the 2006 video game Scarface: The World Is Yours. Tony Montana has become a cultural icon and is one of the most famous movie...

.

Riley seems to have a fair amount of criminal aptitude, as is demonstrated when he helped coordinate the kidnapping of Oprah Winfrey
Oprah Winfrey
Oprah Winfrey is an American media proprietor, talk show host, actress, producer and philanthropist. Winfrey is best known for her self-titled, multi-award-winning talk show, which has become the highest-rated program of its kind in history and was nationally syndicated from 1986 to 2011...

, and further demonstrated by his criticisms of Ed Wuncler III and Gin Rummy for their lack of criminal know-how ("Let's Nab Oprah
Let's Nab Oprah
"Let's Nab Oprah" is the eleventh episode of the Adult Swim animated television series, The Boondocks. It originally aired on February 12, 2006.-Plot:...

"). 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
Gangsta rap
Gangsta Rap is a subgenre of hip hop music that evolved from hardcore hip hop and purports to reflect urban crime and the violent lifestyles of inner-city youths. Lyrics in gangsta rap have varied from accurate reflections to fictionalized accounts. Gangsta is a non-rhotic pronunciation of the word...

 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
Reverse psychology
Reverse psychology is a technique involving the advocacy of a belief or behavior that is opposite to the one desired, with the expectation that this approach will encourage the subject of the persuasion to do what actually is desired: the opposite of what is suggested...

, 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.

When forced to fight, Riley is his brother's exact opposite, resorting to a rather crude and thuggish form of attack. His method is simply to continue attacking, usually with concealed BB guns, and random objects, like vases, or lamps, using whatever means necessary. 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. 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 (like Huey and Butch Magnus) but is able to continue fighting, seemingly ignoring his injuries to a certain limit. In season 3, this thuggish fighting style finally proves its worth in a fight with Lamilton Taeshawn, earning his first single-handed victory in the series. Overall, his fighting style seems to have improved to some degree in the third season.

Riley seems to take great pleasure in poking fun at other people, sometimes to the point where Huey or Robert
Robert Jebediah Freeman
Robert Jebediah "Granddad" Freeman is a fictional character in the animated television show The Boondocks, as well as a regular character in a comic strip of the same name. He lives in the suburb of Woodcrest with his two grandsons, Huey Freeman and Riley Freeman...

 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
Santa Claus
Santa Claus is a folklore figure in various cultures who distributes gifts to children, normally on Christmas Eve. Each name is a variation of Saint Nicholas, but refers to 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
Shopping mall
A shopping mall, shopping centre, shopping arcade, shopping precinct or simply mall is one or more buildings forming a complex of shops representing merchandisers, with interconnecting walkways enabling visitors to easily walk from unit to unit, along with a parking area — a modern, indoor version...

 with airsoft guns ("A Huey Freeman Christmas
A Huey Freeman Christmas
"A Huey Freeman Christmas" is the seventh episode of the Adult Swim animated television series The Boondocks. It originally aired on December 18, 2005.-Plot:After spending some time teaching the class about the traditional Kwanzaa Harambee salute, Mr...

").

Riley's excessive interest in the "thug" lifestyle has made him into something of a misogynist
Misogyny
Misogyny is the hatred or dislike of women or girls. Philogyny, meaning fondness, love or admiration towards women, is the antonym of misogyny. The term misandry is the term for men that is parallel to misogyny...

. He claims that all women are "hoes
Prostitution
Prostitution is the act or practice of providing sexual services to another person in return for payment. The person who receives payment for sexual services is called a prostitute and the person who receives such services is known by a multitude of terms, including a "john". Prostitution is one of...

", 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
The Story of Catcher Freeman
"The Story of Catcher Freeman" is the twelfth episode of the second season of the Adult Swim animated television series The Boondocks and the twenty seventh episode overall. It aired on January 28, 2008.-Plot:...

", 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
Crack cocaine
Crack cocaine is the freebase form of cocaine that can be smoked. It may also be termed rock, hard, iron, cavvy, base, or just crack; it is the most addictive form of cocaine. Crack rocks offer a short but intense high to smokers...

."

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
Graffiti
Graffiti is the name for images or lettering scratched, scrawled, painted or marked in any manner on property....

 as his primary window for artistic gratification until the episode "Riley Wuz Here
Riley Wuz Here
"Riley Wuz Here" is the twelfth episode of the Adult Swim animated television series, The Boondocks. It originally aired on February 19, 2006.- Plot :Riley opens the episode by piecing the side of a neighbor's house...

", 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." 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. In the episode "The Trial of R. Kelly
The Trial of R. Kelly
"The Trial of R. Kelly" is the second episode of the Adult Swim animated television series The Boondocks. It originally aired on November 13, 2005.-Plot:...

": Huey mentions that Riley still wets his bed. It was said again by Granddad in Ballin'
Ballin' (The Boondocks)
"Ballin" is the eighth episode of the second season of the Adult Swim animated television series The Boondocks and the twenty-third episode overall...

.

Riley is said to use the word "Nigga" far more than any other character on the show, this was pointed out in the episode "The S-Word", as he was described as having used it so much, that when his teacher overhears him using it to ask someone to borrow one of his French fries, the teacher was more concerned on how he planned to return the French fries when he was done, than the fact that he used the word.

Riley has a range of nicknames, such as; Young Reezy, The Fundraiser and Riley Escobar.
Pablo Escobar
Pablo Emilio Escobar Gaviria was a Colombian drug lord. He was an elusive cocaine trafficker and rich and successful criminal. He owned numerous luxury residences, automobiles, and even airplanes...


Relationships

Huey Freeman
Huey
Huey Freeman
Huey Freeman is a fictional character of The Boondocks syndicated comic strip written by Aaron McGruder, as well as the main character and recurrent principal narrator of the animated TV series of the same name...

 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"

Ed Wuncler III 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 him 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.

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.

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.
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