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Unlike other characters in the series, Riley has a notorious tendency to drop the N-word on almost everyone, regardless of their skin color. He also tends to use "bitches" as a general term for women. 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. Riley's excessive interest in the "thug" lifestyle has made him into something of a misogynist. 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 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. Believing himself to be phenomenally skilled in basketball but in reality having no such talent. He is brutally honest to the point of being very rude. He is also quite rebellious and does not listen to anyone, especially Huey and Granddad. Riley is quite brash and could often get into situations without considering first, also making him a trouble maker. Which he refers to as getting into someone's "mental mind". 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. In several instances he is shown to be very resourceful and pragmatic, and "beats" Tom, a district attorney, in an argument over R. 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".ĭespite his pretensions to the contrary, Riley is nowhere near stupid.
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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". He also refused to believe that the rapper was gay despite the obvious clues to the contrary. This is further shown in "The Story of Gangstalicious Part 2" where he dresses in effeminate clothing only because Gangstalicious created the style. 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. 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. He embraces the stereotypical "gangsta" lifestyle, doing his best to promote the urban culture in the contrasting suburb of Woodcrest. Riley is a highly impressionable third grader.