Riley Freeman is a character from the
syndicated comic strip
A comic strip is a sequence of drawings, often cartoons, arranged in interrelated panels to display brief humor or form a narrative, often serialized, with text in balloons and captions. Traditionally, throughout the 20th and into the 21st ...
''The Boondocks'' written by
Aaron McGruder
Aaron Vincent McGruder (born May 29, 1974) is an American writer, cartoonist, and producer best known for creating ''The Boondocks'', a Universal Press Syndicate comic strip and its animated TV series adaptation.
Early life and education
Aaron ...
and its
TV series
A television show – or simply TV show – is any content produced for viewing on a television set which can be broadcast via over-the-air, satellite, or cable, excluding breaking news, advertisements, or trailers that are typically placed betw ...
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 younger 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
The South Side is an area of Chicago, Illinois, U.S. It lies south of the city's Loop area in the downtown. Geographically, it is the largest of the three sides of the city that radiate from downtown, with the other two being the north and we ...
, was moved along with his brother to Woodcrest, a peaceful, white suburb of
Baltimore
Baltimore ( , locally: or ) is the List of municipalities in Maryland, most populous city in the U.S. state of Maryland, fourth most populous city in the Mid-Atlantic (United States), Mid-Atlantic, and List of United States cities by popula ...
,
Maryland
Maryland ( ) is a state in the Mid-Atlantic region of the United States. It shares borders with Virginia, West Virginia, and the District of Columbia to its south and west; Pennsylvania to its north; and Delaware and the Atlantic Ocean to ...
by their
granddad. Riley is eight. 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 Rene King (born January 15, 1971) is an American actress and director. She is the recipient of various accolades, including an Academy Award, a Golden Globe Award, and four Primetime Emmy Awards. In 2019, ''Time'' magazine named her one ...
. It is strongly suggested that Huey and Riley's birth parents are deceased.
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 tends to defend his idols even when his imitations go against common sense and righteousness. One example is his support of ]R. Kelly
Robert Sylvester Kelly (born January 8, 1967) is an American singer, songwriter, record producer, and sex offender convicted of racketeering and multiple sex offenses.
During his recording career, Kelly sold over 75 million records worldwid ...
in "The Trial of R. Kelly
The first season of the animated television series, ''The Boondocks'' originally aired in the United States on Cartoon Network's late night programming block, Adult Swim. Season one started on November 6, 2005, with "The Garden Party" and ended w ...
": 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 second season of the animated television series, ''The Boondocks'' originally aired in the United States on Cartoon Network's late night programming block, Adult Swim. The second season features 15 episode, it originally premiered on October ...
" where he dresses in effeminate clothing because Gangstalicious created the style. In order to be like his idols, he collects airsoft
Airsoft is a team game in which participants eliminate opposing players by tag (game), tagging them out of play with airsoft pellets, spherical plastic projectiles shot with mock air gun, air weapons(usually powered by an electronic motor) call ...
weapons and tags houses, as demonstrated in " The Garden Party" and "Riley Wuz Here
The first season of the animated television series, ''The Boondocks (TV series), The Boondocks'' originally aired in the United States on Cartoon Network, Cartoon Network's late night programming block, Adult Swim. Season one started on November 6 ...
". 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
Antonio Montana is a fictional character and the protagonist of the 1983 film ''Scarface''. This character is portrayed by Al Pacino in the film and is voiced by André Sogliuzzo in the 2006 video game '' Scarface: The World Is Yours''. Embod ...
.
Riley seems to have a fair amount of criminal aptitude, as is demonstrated when he helped coordinate the kidnapping of Oprah Winfrey
Oprah Gail Winfrey (; born Orpah Gail Winfrey; January 29, 1954), or simply Oprah, is an American talk show host, television producer, actress, author, and philanthropist. She is best known for her talk show, ''The Oprah Winfrey Show'', br ...
, and further demonstrated by his criticisms of Ed Wuncler III and Gin Rummy
The following is a partial list of characters who have appeared in the animated television series, ''The Boondocks''.
Main characters
The Freeman family
The Freeman family in ''The Boondocks'' series is portrayed as an all-male, African-American ...
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
Gangsta rap or gangster rap, initially called reality rap, emerged in the mid- to late 1980s as a controversial hip-hop subgenre whose lyrics assert the culture and values typical of American street gangs and street hustlers. Many gangsta rappe ...
lifestyle he seems to have a level of street smarts
''Street Smarts'' is an American game show that featured two in-studio contestants trying to predict the outcome of interviews of people who were found on the street. The show, which was hosted by Frank Nicotero, aired in syndication from 2000 t ...
possibly as great as his brother, often able to manipulate situations through lying and reverse psychology Reverse psychology is a technique involving the assertion 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 is actually desired. This techniqu ...
, which he refers to as getting into someone's "mental mind". Despite his crude thuggish lifestyle on rare occasions he has displayed acts of compassion (giving $100 to a panhandler he previously ignored and spat at).
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 which seem rooted in martial arts
Martial arts are codified systems and traditions of combat practiced for a number of reasons such as self-defense; military and law enforcement applications; combat sport, competition; physical, mental, and spiritual development; entertainment; a ...
. 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. His street-fighting style has improved to a certain degree in season 3, best seen when he defeated Lamilton Taeshawn in the episode “Smokin’ With Cigawettes”. 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 has been shown he has a great understanding of the media world and music industry. This was shown when he tried to advise Thugnificent against starting a rap war with a much younger aspiring rap star Sgt. Gudder, knowing it would only cause unnecessary problems.
Riley is a talented artist, particularly with graffiti. His art is both eclectic and deep, ranging from depicting everyday objects to people. He has a creative manner of stylizing letters as well.
Relationships
; Huey Freeman
Huey Huey, used as a given name, is a variant of Hughie. It may refer to:
People
* Huey (rapper) (1987–2020), American rapper
* Huey Dunbar, Puerto Rican salsa singer
* Huey Johnson (1933–2020), American environmentalist and politician
* Huey Lewis ...
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 grandfather is not around, Huey usually will not hesitate to set Riley straight himself. In "...Or Die Trying", Riley does not have any problem with 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
Grandparents, individually known as grandmother and grandfather, are the parents of a person's father or mother – paternal or maternal. Every sexually-reproducing living organism who is not a genetic chimera has a maximum of four genetic ...
. Riley constantly disrespects Robert and 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. He seems to not understand his grandpa's rules and gets whipped with his belt 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 are 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
Prison rape or jail rape refers to sexual assault of people while they are incarcerated. The phrase is commonly used to describe rape of inmates by other inmates, or to describe rape of inmates by staff.
China
In February 2021, BBC News repo ...
. 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. Her appearance in the TV series is similar to that of Cammy
, also referred to by her codename , is a fictional character in the ''Street Fighter'' fighting game series. She debuted in 1993 as one of the four new characters in ''Super Street Fighter II: The New Challengers''. She has also been featured in ...
from the ''Street Fighter
, commonly abbreviated as ''SF'' or スト (''Suto''), is a Japanese media franchise centered on a series of fighting video and arcade games developed and published by Capcom. The first game in the series was released in 1987, followed by six ...
'' series.
; Lamilton Taeshawn
Due to their gangsta-like behavior depicted in the episode "Smokin' with Cigarettes," Riley is initially shown to be friends with Lamilton Taeshawn, as they enjoy hanging out with each other and doing bad things, such as causing a car-pile up, going on a joyride on Lamilton's grandmother's car that he stole, and smoking with cigarettes. However, Lamilton shows more of his sociopathic
Psychopathy, sometimes considered synonymous with sociopathy, is characterized by persistent antisocial behavior, impaired empathy and remorse, and bold, disinhibited, and egotistical traits. Different conceptions of psychopathy have been u ...
behavior when he enjoys movie scenes of people being murdered, as well as killing a dog while trespassing into his owner's property, and even assaulted his grandmother when she refused to buy him chicken. These events start to disturb Riley greatly, and ever since then, Riley finds Lamilton to be so disturbing and sick in nature and refuses to hang out with him again, and Lamilton would often try to kill Riley in return, resulting the two kids to have a brawl in the school rooftop. Despite his enmity with Lamilton, Riley cannot bear to kill him as he tried his best to prevent Lamilton from falling off the school rooftop, though Lamilton did fall (thanks to his former psychologist Dr. Doomis forcing Riley to let him go), but survived.
; Thugnificent
Thugnificent (Otis Jenkins) is Riley's favorite rap artist and neighbor. What can best be described as a "Professional Buffoon", Thugnificent was the leader of the group Lethal Interjection Crew. He had taken a liking to Riley and allowed him to join after irresponsibly having Riley perform several reckless and dangerous stunts. Riley and Thugnificent remained friends even after the downfall of Thugnificent's career.
Footnotes
{{DEFAULTSORT:Freeman, Riley
The Boondocks characters
Animated human characters
Black characters in animation
Black people in comics
Child characters in animation
Child characters in comics
Child characters in television
Comics characters introduced in 1999
Fictional African-American people
Fictional businesspeople
Fictional characters from Chicago
Fictional characters from Maryland
Fictional criminals
Fictional orphans
Fictional victims of domestic abuse
Male characters in animated series
Male characters in comics