Welcome to Woodcrest, Home of the Freeman Family. This is the subreddit dedicated to the series created by Aaron Macgruder.
I'm gonna preface this by saying that I think Huey is taken way too seriously as a character and Riley isn't taken seriously enough.
I think their childish antics are just that...childish. Neither child recognizes the true impact of what they are doing. The episodes that focus on them actually show neither one of them are truly about that life. They don't get the gravity of the things they do and say.
Huey would grow up to make his voice and ideas heard. He'd write a book and it'd win a Pulitzer Prize. He would write a movie or a TV show that's critically acclaimed. The one time the feds do come for him it's because Wuncler set him up. His issue is that nobody listens to him. He doesn't have enough charisma to be a true threat.
Riley would grow up to be in sales and at worst, he gets shot in his teens playing around in Chicago. He has shown several times he's NOT about that life and doesn't take anything seriously. Hence why he never sticks to one thing each episode outside of the Riley Wuz' Here episode, where he is actually challenged and given healthy expectations for the first time when Bob throws his art in the trash and doesn't enable his antics. Without proper guidance, he would have to learn the hard way...but it's been shown that both boys can and will learn..
Also, being a hypocrite seems to run in the family tbh. All of the men in their family have less than ideal qualities and still seem to lead relatively normal lives. Granddad is selfish and moves to the suburbs and claims to be a civil rights activist. Jericho takes over Granddad's home and keeps the money. Tobias tries to shoot Thelma and kills massa on accident. At least one of them is not going to do what they say they're going to do...and I'd bet money that it's Riley.
They're both just two different sides of Aaron Mcgruder when he moved to Maryland. The kid who drew and didn't feel connected to his teachers, who didn't feel heard. And Huey is just Aaron Mcgruder basically getting exasperated when nobody ever listens.
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Riley would end up like me and my friends growing up. 3/5 would end up doing time, two would dodge the bullet somehow, probably realize it, turn their shit around and because of being charismatic be able to "make it" in life.
I don’t even think it would take that much. You see how quickly he straightened out after things with Lamilton went left?
Riley likes the idea of being a thug. He’s not passionate about anything but his money, which would arguably set him up to do more of a white collar crime tbh, but that’s another theory for another day.
Give Riley more credit than that. Sure causes trouble every now and then but he'd never fully live a gangster life. Just the sight of a dog getting shot made his stomach turn,deep down he has a heart. I know Riley seems like a slacker who doesn't care about his future,but when he actually cares about something he commits to it. Like the episode with Graffiti he managed to make all that art work at 8 years old. Becoming an artist would be a perfect future for Riley,he gets to express him self trough art rather than vandalism.