the opposite of his brother Huey, while Huey is politial, Riley acts like a "gangsta" and is a more typical kid than Huey is
Riley is a highly impressionable third-grader who tightly embraces the stereotypical "gangsta" lifestyle, doing his best to promote the urban culture in the contrasting suburb of Woodcrest. Riley trys to be a stylish black funk gangster. Influenced by the mass media by way of 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 shouldn't have to miss out on his next album because of Kelly going to jail. This is further shown in "The Story of Gangstalicous" where he dresses in effeminate clothing only because Gangstalicous created the style (refusing to believe that the rapper was gay despite the obvious signs). 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 also seems to be 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 stupid: 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".
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 doesn't listen to anyone, especially Huey and Grandad. He is brutally honest to the point of being very rude.
Riley sometimes overestimates his own rather 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. He does seem to have some talent with airsoft guns, as he fought Huey to a tie in season two (he was more heavily armed, though). It can be shown that he has a strong amount of endurance and determination, seen when he receives many harsh attacks from his opponents (like Huey and Butch Magnus) but is able to continue fighting, seemingly ignoring his injuries to a certain limit.
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, though 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
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.
Riley is somewhat cynical. In "The Story Of Catcher Freeman", he recognizes that the stories of his Granddad usually are made-up: this can mean that he is, like his brother, a realist. He can keep a cool head, even under pressure: when both he and his idol Gangstalicious are under heavy gunfire, Riley remains stable while the supposedly hardcore Gangstalicious loses his composure, causing Riley to opine that Gangstalicious is a fraud, lamenting, "It's like going to heaven and finding out God smokes crack."
Despite these less than admirable characteristics Riley is precociously clever, especially when required to think quickly or talk his way out of trouble. Usually he's able to get what he wants by manipulating people or disadvantageous events, like he did in "Let's Nab Oprah" - first with his Granddad, then when he saw Huey at the studios. He is also an extremely talented visual artist and had been using graffiti as his primary window for artistic gratification until the episode "Riley Wuz Here", during which he learns to paint selflessly and for the benefit of the viewer instead of personal glory. He still, however, admits that he hopes his artistic talent lets him "get paid." One might say it's the heavy influence of mass media, particularly modern-day rap culture, that inhibits his intellectual potential. Thus, Riley's characterization is McGruder's way of satirizing many youths today who have the potential to do so much but choose to waste it, and instead end up in trouble with the law or worse. In the episode "The Trial of R. Kelly": Huey mentions that Riley still wets his bed. It was said again by Granddad in Ballin'.
Riley is said to use the word "Nigga" far more than any other character on the show, this was pointed out in the episode "The S-Word", as he was described as having used it so much, that when his teacher overhears him using it to ask someone to borrow one of his French fries, the teacher was more concerned on how he planned to return the French fries when he was done, than the fact that he used the word.
Riley has a range of nicknames, such as; Horsechoker, H.R. Paper Stacks, Louis Rich, Young Reezy, Pillsberry Doughboy, Dat Nucca, The Fundraiser and Riley Escobar.
Huey and Riley tend to have a regular brotherly relationship despite their contradictory personalities. Riley looks up to his older brother by beating up people. Due to the blunders Riley makes, Huey inevitably tries to teach him the error of his ways, but often to no avail. When their granddad isn't around, Huey usually will not hesitate to set Riley straight himself. In "...Or Die Trying" Riley doesn't have any problem at 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")
Riley constantly disrespects Robert. 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 doesn't influence or change his actions in any significant way. Riley seems to not understand his grandpa's rules and gets whipped when he makes a bad choice. They are shown to be close at times and agree on things in Season 2.
Ed Wuncler III and Gin Rummy
Riley hangs out with them and refers to them as his "niggas" because they're 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 city. Riley sometimes accompanies them on their various misdeeds, and isn't 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 won't reveal they did it, then when it was eventually returned, they stole his new bike, fitted with rims riding as they shouted: "Thanks 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 (Butch Magnus) or when he and Huey need to seek out the X-box Killer.
Riley likes to make fun of the Dubois family – especially Tom. He mocks Tom's un-manliness, 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. He also mocks Sarah's cooking by comparing her peach cobbler to vomit with peas in it. He hates Jazmine's when she does not listen to him like when she did not give him lemonade when it was only a dollar he says""I ain't got no dollar.""
Cindy would be considered the white counterpart of Riley (except for the fact that they are both "gangsta") and is initially an antagonist to Riley as seen in the Season 2 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 episode, The Fundraiser, Cindy became a business partner of Riley's and helped him Jasmine, and a seldom used stereotypical ignorant kid sell large amounts of chocolate in order to make money.
Many people believe that Cindy and Riley would make a good couple because of there close personalities. There is nothing that has been said about this and may only remain as controversy. However, in "The Fundraiser", Riley stated that one of the things he really likes about Cindy is that "she has less compassion than the average girl".
Huey Freeman, Riley’s brother have some tough altercations when they’re alone. They fight, have airsoft gun wars, and annoy their granddad, Robert Freeman. The consequences for their actions results in their granddad whipping out the belt and striking the kids or tying up their legs and pulling the belt which makes them trip and fall. In the episode “Home Alone” Huey tied up Riley and locked him in the closet. Riley escaped after chewing up the tape Huey wrapped around his arms and opening the door.Then they had an airsoft battle, which ended when they both shot each other in the face at the same time from point blank range, which knocked them out when they fell and hit the ground.
Riley has a deep hatred for a large white 11 year old Butch Magnus (to whom he refers to as Bitch Magus). The reason for his dislike is that Butch had snatched Riley's platinum and diamond chain that he received from Thugnificent. Another reason that Riley does not like to Butch is that every time Riley attempted to get the chain back he was beaten and bloodied in front of others.
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