Riley Freeman is a character from syndicated comic strip The Boondocks written by Aaron McGruder and its TV series adaptation.

Riley Freeman is an impressionable third grader who embraces the stereotypical "gangsta" lifestyle and lives his life like his idol rappers.

In order to be like his idols, he collects airsoft weapons and tags houses, as demonstrated in "The Garden Party" and "Riley Wuz Here".

Despite his pretensions to the contrary, Riley is not simpleminded: 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".

Despite his crude thuggish lifestyle on rare occasions he has displayed acts of compassion (giving $100 to a panhandler he previously ignored and spat at).

His thuggish fighting style, both with weapons and hand-to-hand, failed several times against the precision of Huey's martial arts ability.

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").

They have a great variety of real firearms and are free to commit any crime they wish since Ed's grandfather essentially owns the suburb.

However, they tend to use him for their own personal gain, such as stealing his Granddad's car with knowledge that Riley will not reveal they did it, then when it was eventually returned, they stole his new bike, fitted with rims riding as they shouted: "Thank you 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 or when he and Huey need to seek out the Xbox Killer.

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 Season 3 episode "The Fundraiser", Cindy became a business partner of Riley's and helped him, Jazmine, and Phil, a seldom used stereotypical ignorant kid, sell large amounts of chocolate bars in order to make money.

However, Lamilton shows more of his sociopathic behavior when he enjoys movie scenes of people being murdered, as well as killing a dog while trespassing into his owner's property, and even assaulted his grandmother when she refused to buy him chicken.