Riley Freeman
Photo Credit: Everett Collection

Riley Freeman

The Boondocks

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About Him

Grew Up... in Chicago. Riley was born and raised on the South Side of Chicago along with his older brother Huey. It was there that he discovered his passion for “street life.”

Living... in Woodcrest, Maryland. After the death of their parents, Riley and his brother went to live with their grandfather. Using the children’s inheritance money, Granddad moved the family to the affluent, white suburb of Woodcrest. Inevitably, the town’s privileged culture clashes with Riley’s desire to remain as “hood” as possible.

Profession... wannabe gangsta. Riley idolizes famous rappers and gangsters like Gangstalicious and Thugnificent ft. Lethal Interjection. He does everything he can to become more like them. For someone so young, he’s off to a great start in doing just that.

Interests... showing off. Whether it’s wearing a big shiny chain or a questionable new hip-hop fashion line, Riley likes to show off how cool he is. However, as his cocky but ultimately abysmal basketball performance demonstrates, it’s mostly posturing.

Relationship Status... single. Riley is still a child, but he has internalized a less-than-healthy view of gender norms through his worship of “gangsta” culture, including intense homophobia. His more progressive brother Huey tries to explain how this reflects poorly on black culture at large, but Riley will just respond with “N*gga, you gay,” inadvertently proving Huey’s point.

Challenge... getting money. As an aspiring hustler, Riley wants to get those dollar bills. So he’ll do anything from taking over a Girl Scout cookie racket, to teaming up with the already rich psychopath Ed Wuncler III, to kidnapping and ransoming Oprah Winfrey.

Personality... immature. Riley is an impressionable, not-as-smart-as-he-thinks kid who has so far learned all of the wrong lessons from the worst parts of popular hip-hop culture. He just doesn’t know any better. Fortunately, there is still plenty of time for him to grow up.

Riley Freeman's popularity ranking on CharacTour is #3806 out of 5,600+ characters. See our top-ranked characters and read their profiles.

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