Riley Freeman is a character from the fictional TV series, The Boondocks. He is Huey's eight-year old brother who aspires to be like the rap artists and the gangsters he admires. This obsession molds him and makes his personality the exact opposite of his brother. Riley is voiced by Regina King.

Riley is a gangster wannabe who wants to be as "gangsta" as the rap artists and the gangsters he sees on TV. He frequently uses incorrect grammar in order to sound "gangsta". He tends to defend his idols even though it goes against common sense. One example is supporting R. Kelly in "The Trial of Robert Kelly" even though there is overwhelming evidence that proves the R. Kelly did urinate on an underage girl. In order to be like his idols, he collects airsoft weapons and tags houses, as demonstrated in "The Garden Party" and "Riley Wuz Here".

Also, he seems to be very intelligent and have more common sense than most of the characters on the show than he lets on. This is demonstrated when he coordinated the kidnapping of Oprah and insulting Ed Wuncler III and Gin Rummy for not knowing what "intel" meant in "Let's Nab Oprah". However, this also creates a narcissistic trait. He overestimates his abilities, which usually orchestrates his downfall. An example is fighting with Huey in "Let's Nab Oprah". He employed many sneak attacks, but lost the fight. Riley also brags a lot and calls anyone who tries to knock him down a notch, "haters". However, he shows an artistic side when he tags murals on people's houses.

Riely's fascination with weapons and his "gangsta" ways makes him a sadist. He often hangs out with Ed and Rummy, but only because they have access to real weapons. Also, when someone does something humiliating, he makes fun of them until Huey or until Robert has to hit him. He also assaulted Santa Claus for not getting what he wanted for Christmas in "A Huey Freeman Christmas".

His actions make him seem very disrespectful. He called the prisoner he talked to gay and he blamed the victim for being victimized in "The Trial of Robert Kelly". He also shown disrespect towards women. Riley states that all women are hoes because you have to pay to take them out for dinner and he used the term "bitches" for a general term for women. In the "Garden Party", it is implied that he is racist towards Caucasians, as he made fun of the way they talk. He also demonstrates blasphemous qualities as he expresses that he is better than God.

Huey and Riley tend to have a regular brotherly relationship despite their contradictory personalities. Due to the blunders Riley makes, Huey has teach him the error his ways. Huey is always trying to teach Riley the real concept of an idea. Also, when Riley gets out of hand, Huey has to set him straight.

Riley constantly disrespects Robert. Robert mainly beats Riley when he does something that he thinks is unacceptable such as saying "Ho" or lying. This clearly shows that Robert is mortified by Riley and would rather by rid of him and Huey. However, in "The Real", they do work together to con Xzibit.

Riley hangs out with them in order to use real weapons. He accompanies them on their various crimes. He also points out to them that they get away with their poorly-planned crimes because Ed's grandfather is the mayor, who has the police on his payroll. However, Rummy dismisses Riley's reasoning and says they get away with crimes because he is a criminal mastermind. Also, when Ed and Rummy have a friendly hug, Riley calls them gay.

Riley likes to make fun off the Dubois family especially Tom. He mocks Tom's unmanliness, breaks Jazmin's beliefs, and makes fun of Sarah's cooking. He also demonstrates his great argument skills to Tom in "The Trial of Robert Kelly" by saying that the victim is old enough to be accountable for being urinated on and makes fun of Tom's fear of anal rape in "A Date With The Health Inspector". He seemingly emotionally scars Jazmin when he assaults Santa. Finally, he mocks Sarah's cooking by comparing her peach cobbler to vomit with peas in "The Itis". However, they take it and they don't hold it against him.

• "The Boondocks" on TV.com

• "Let's Nab Oprah"