Riley, Huey’s ten-year-old twin brother, could be described as a product of mass media influence, in that he, though young, refers to women as “bitches” or “hos,” frequently alludes to his “rep” and his status on the “streets,” and idolizes gangsta rappers and their lifestyle. Though he, indeed, would seem to be everything his brother is not, he has demonstrated his ability to rationalize and plan things out, such as when he rendered Tom Dubois, an attorney, speechless after debating with him regarding the R. Kelly trial in “The Trial of R. Kelly”. His criminal aptitude is put to the test when he goes on some crime sprees with the incompetent Ed Wuncler III and Gin Rummy in the episode “Let’s Nab Oprah”, during which he effectively acts as the brains behind the operation to kidnap Oprah.
Riley can be seen as representative of the misguided black youth. He has a fascination for firearms, and his tendency for violence is displayed time and time again. At Christmas, he declared himself “The Santa Stalker” and attacked the Santa at the local mall with airsoft Glock17s, hitting many innocent bystanders. Riley does not own any real firearms and has only been seen owning Airsoft-style guns a Glock 17and an MP5K but he pals around with Ed Wuncler III and Gin Rummy, who have on occasion granted him access to real weapons.
Indeed though, beyond this tough-guy facade, there would seem to be some measure of sensitivity that is especially apparent in the episode “Riley Wuz Here”, during which he learns to use his incredible artistic abilities to create art for the sake of creating art, and not for personal glory.