Riley Freeman

Riley Freeman is the deuteragonist of The Boondocks  (2005). He is Huey Freeman's younger brother and Robert Freeman's youngest grandson. He is an 8–year-old who emulates the gangster lifestyle. He and many others commonly refer to him as "Riley Escobar", "Young Reezy", and "The Fundraiser".

Personality
Riley is a highly impressionable third grader. He embraces the stereotypical "gangsta" lifestyle, doing his best to promote the urban culture in the contrasting suburb of Woodcrest. Influenced by the mass media via 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 Kelly's guilt, Riley believes he should not have to miss out on his next album because of Kelly going to jail. This is further shown in "The Story of Gangstalicious Part 2" where he dresses in effeminate clothing only because Gangstalicious created the style. He also refused to believe that the rapper was gay despite the obvious clues to the contrary. In an effort to further emulate the lifestyle he praises, he collects airsoft weapons and tags houses, as demonstrated in "The Garden Party" and "Riley Wuz Here".

Riley seems to have a fair amount of criminal aptitude, as is demonstrated when he helped plan 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 in "Let's Nab Oprah".

Despite his pretensions to the contrary, Riley is nowhere near stupid. In several instances he is shown to 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". 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.

Riley overestimates himself extremely. Believing himself to be phenomenally skilled in basketball but in reality having no such talent. The same was seen in kickball.

Riley seems to take great pleasure in poking fun at other people, sometimes to the point where Huey or Robert have to hit him to make him stop, although such disciplinary actions usually have no effect on his behavior. He also holds grudges; he has a grudge, for example, against 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 Santa's with airsoft guns ("A Huey Freeman Christmas").

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 recognize. He also tends to use "bitches" as a general term for women.

Unlike other characters in the series, Riley has a notorious tendency to drop the N-word on almost everyone, regardless of their skin color. His fight with Butch Magnus and interview with Werner Herzog are two examples.

Villainous Acts

 * He shoots Ed out of a window in The Garden Party.
 * He supports R. Kelly in The Trial of R. Kelly.
 * He steals a car along with Gangstalicious in The Story of Gangstalicious.
 * He attacks "Santa Claus" in the mall to make him pay what he owes because he didn't get his presents but fails repeatedly in A Huey Freeman Christmas.
 * He makes fun of Martin Luther King Jr. during dinner in Return of the King.
 * He attempts to kidnap Oprah, along with Ed and Gin Rummy despite failing repeatedly due to Ed and Rummy's stupidity in Let's Nab Oprah.
 * He graffitis on a neighbor's house in Riley Wuz Here.
 * He refuses to confess who stole Robert's car in Thank You for Not Snitching.
 * He wastes the food money Robert left in the cabinet on clothes and tries to leave the house with several attempts but fails repeatedly due to Huey always catching him.
 * He rides along with Lamilton Taeshawn who stole his grandmother's car and wrecks it in the process and joins him on pulling pranks to people around town.

Trivia

 * Riley fighting skills are very poor as he constantly loses fights to everyone he tries to fight but in the Season 3 episode Smokin with Cigarettes he fought Lamilton and fights him off with a couple of jabs and in Season 4 he is also acrobatic, by somersaulting in the air to turn one of the lights off.
 * Riley gets beaten the most by Robert because he constantly disrespects him and Robert will grab his belt and beat Riley to keep him in line.