Riley Freeman

“	N***a, you gay! 	„
 	~ Riley's catchphrase.	
Riley Freeman is one of the two main protagonists (alongside his older brother Huey) of the animated series The Boondocks and original comic strip.
He is the eight-year-old younger brother of Huey Freeman, making Riley the youngest grandson of Robert Freeman and the youngest person in their house. Same as his brother, Robert moved them to the suburban city of Woodcrest, where their lives changed for the better or worse depending on the situation. Unlike Huey, Riley, more of an urban youth who emulates the typical gangster lifestyle, being known as a public menace, is known for causing numerous issues for the people around him. Believing himself to be better than his brother and others in general, looking up to the wrong people, and same as his grandfather, Riley often causes their family troubles.
Despite being one of the series' main characters, he has done the most antagonistic things and committed crimes, ranging from graffitiing neighbor's houses, going on constant crime sprees with his two best friends, Ed Wuncler III, and Gin Rummy, two grown men from the military, who have attempted numerous crimes, but got away, because the two are well-off Caucasian men.
Like his brother Huey, he was voiced by Regina King.
== 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". He has no issue in committing the crimes that he has shown, no matter the situation or cost. This is further shown when Riley and Lamilton had no trouble pushing a flaming bed and naked dolls over a bridge, causing an assortment of accidents and potential injuries, because of that. He and him shot guns filled with urine and hot sauce at people, all while they laughed about it.
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 troublemaker. 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, has no such talent. The same was seen in kickball, where is completely misses the ball and got a strikeout despite his promise to get a home run. For the former sport, he is shown to have very poor shooting skills and hogs the ball too early which causes his team to lose 3 games in a row.
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 ==
=== In General ===
* He constantly disrespects his grandfather Robert, as well as his brother Huey and his friends and many others.
* He goes on crime sprees or simply commits crimes on a daily basis.
* He looks up to many criminals and gangsters.
* He is homophobic, as he repeatedly slanders anything he considers "gay." In fact, in "The Fried Chicken Flu," he calls the "Woodcrest Fried Chicken Flu Militia" "f*****ts."
* Whenever Robert does something irresponsible or even dangerous, Riley supports and sometimes goes along with his plans despite Huey warning them of the consequences, which always leads to something bad. In most cases, he encourages and even convinces Robert to commit said acts in the first place.
** This is best shown in "Breaking Granddad," where he gives him the idea to sell hair gel made out of an explosive compound to the public despite the fact it could explode and kill people when caught on fire. Even when the truth is revealed on the news, they still plan to make more to sell to Boss Willona.
* He, along with Robert, refuse to listen to Huey's warnings even though he's right and sometimes goes against his advice, which is shown when they invite their friends into their home during a pandemic despite Huey only planning for them and Jazmine in "The Fried Chicken Flu." This also leads to major consequences later on.
=== Season 1 ===
* He shoots Ed out of a window in "The Garden Party."
* He supports R. Kelly despite his obvious guilt in "The Trial of R. Kelly." He even got his brother to stop his protests to the ignorant jury.
* He steals a car along with the rap artist Gangstalicious in "The Story of Gangstalicious."
* He stalks and attacks Mall Santa in the mall with airsoft guns to make him pay what he owes because he did not get his presents but fails repeatedly and also attacks Uncle Ruckus in the end 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, but fails repeatedly due to Ed and Rummy's stupidity in "Let's Nab Oprah."
* He graffitis on a neighbor's house in "Riley Wuz Here."
=== Season 2 ===
* He illegally records the movie "Soul Plane 2: The Blackjacking" when he, Huey, Robert, and Jazmine were at the movies and even convinced Robert to leave Jazmine behind and he leaves her with the camera to get caught in "...Or Die Trying."
** He also did it again in "Pause."
* He refuses to confess who stole Robert's car which was Ed and Rummy, even when he and Robert could go to jail to preserve his "street cred" 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 stopping him in "Home Alone."
=== Season 3 ===
* He rides along with Lamilton Taeshawn who stole his grandmother's car and wrecks it in the process and joins him in pulling pranks on people around town in "Smokin' with Cigarettes."
* He and his brother Huey were caught fighting with 5 kids and are assigned to attend a "Scared Stiff" program at William Horton Prison as punishment in "A Date with the Booty Warrior."
=== Season 4 ===
* He digs Robert's iPhone from the trash (meant to be put in the trash for Siri becoming psychotic) and uses it thus making Siri stalk Robert even more in "I Dream of Siri."
* He tells a kid who was dancing and twerking in the cafeteria as his school that that was "gay" and gets targeted for using offensive language and was to run a track and called the other kids who was about to run a track "retards" which leads to them stomping on Riley and chasing him on the track in the end in the series finale "The New Black."
== Trivia ==
* Riley fighting skills are very poor as he constantly loses fights to everyone he tries to fight, though his fighting skills have shown to be improving 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 out of the two brothers because of his constant disrespectful behavior and Robert will grab his belt and beat Riley to keep him in line.
* He has a habit of calling anyone "b***h a$$ n****s", no matter what their color or race is. Sometimed as an insult, other times as a sign of respect.