| Series: | The Boondocks |
| Riley Freeman | |
| Relatives: | Huey Freeman (brother) Robert Freeman (grandfather) Cookie Freeman (great aunt) Jericho Freeman (fourth cousin) |
| Creator: | Aaron McGruder |
| Species: | Human |
| Gender: | Male |
| Nationality: | American |
| Voice: | Regina King |
| First: | "The Garden Party" (2005) |
| Last: | "The New Black" (2014) |
Riley Freeman is a character from syndicated comic strip The Boondocks written by Aaron McGruder and its TV series adaptation.[1] 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.[2]
Riley, who grew up on the South Side of Chicago, was moved along with his brother to Woodcrest, a peaceful, white suburb of Baltimore, Maryland 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. It is strongly suggested that Huey and Riley's birth parents are deceased.
Riley Freeman is an impressionable third grader who embraces the stereotypical "gangsta" lifestyle and lives his life like his idol rappers.[1] 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 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 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. 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.
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 from the Street Fighter series.
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.
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