Riley Freeman is a third grader who has been said to have moved from Chicago to Baltimore, Maryland with his brother Huey Freeman now lives with their grandfather, Robert Jebediah Freeman. It is rumored the reason for the brothers to move was because their birth parents are diseased. Riley is often regarded as a stereotypical "gangsta" who enjoys acting like one. He imitates the lifestyles of rappers and celebrities which makes it inevitable for him to defend his idols, despite going against common sense. People often find Riley Freeman as a rude kid because of how he expresses himself and act as a person. He tends to be brutally honest without sugarcoating anything he says. It is still unknown why he is such a rebellious and disrespectful individual, but can be found being punished by his grandfather on many occasions. Riley Freeman also refers to himself as "Riley Escobar," and "Young Reezy" in an attempt to start his "gangsta" life.
Riley's grandfather's name is Robert Jebediah Freeman. Riley is known to disrespect his grandfather on a daily basis. This mostly causes his grandfather to resort to physical punishment to show him some discipline. However, Riley Freeman has accustomed to the pain of his grandfathers physical punishment to where it no longer has any effects on him which prevents and changes in his actions and behaviors. Surprisingly, people have found moments where he and his grandfather were close and agreeing with one another.
Many people find it difficult to believe that Riley Freeman and Huey Freeman are brothers because of their different personalities. The two are almost the complete opposite of the other. When their grandfather is not supervising, Huey does not hesitate to protect his brother Riley from all sorts of trouble. People claim that Riley would usually regard to his brother with repeated phrases of vulgar insults despite his brothers good intentions.