Riley Freeman
Fictional characterWikipedia
32
MENTIONS
7
EPISODES
6
PODCASTS
Search complete. 32 mentions across 7 episodes found for "Riley Freeman".
Oct 15, 2026
BooHOST
Oh, yeah.
BooHOST
He's got shades of Riley Freeman to him.
BooHOST
He does.
BooHOST
Let's give Riley Freeman a giant robot and see what happens.
BooHOST
In that last page, he actually looks like Riley Freeman when he's got the stick over his head.
Evan JohnsHOST
He does.
Evan JohnsHOST
My dad gave me a robot.
Evan JohnsHOST
Oh, sorry.
DJHOST
So I, I love the way they start it.
DJHOST
It's so real the way they start this to how an eight-year-old would act, where it's like Riley is going like, "Oh yeah, uh, Granddad-
Will the GreatestHOST
[laughs]
DJHOST
...
DJHOST
In Chicago, yeah
Will the GreatestHOST
...
Will the GreatestHOST
I think this, following the episode with the painting from, from last time Riley was here, I think this is like the second or third bit of info we get as far as like lore to-
DJHOST
Yeah
James LewisHOST
I said good basketball player.
James LewisHOST
Like Riley Freeman said, I saw something and I said something.
James LewisHOST
Look it up.
James LewisHOST
But the narrative doesn't fit for Breonna Stewart because she went to Connecticut and she played basketball in the Northeast with African-American people around the African-American culture.
Jessica MarieHOST
She also had a role in a teen romantic comedy, A Cinderella Story, which opened doors for her 2005 role in Miss Congeniality 2, Armed and Fabulous.
Jessica MarieHOST
She stepped into voice acting by voicing Huey and Riley Freeman in The Boondocks.
Jessica MarieHOST
I was young when I first watched the series, so I didn't realize Regina voiced them both until I got older.
Jessica MarieHOST
I thought she was so talented for being able to embody two completely different personalities so effortlessly.
Bobby BonesSOUNDBITE_SPEAKER
Yeah.
ChrisHOST
And, uh, w- I'd love to have her on the podcast, but another actress who I think does an incredible job is Regina King on The Boondocks, you know, playing both Riley and, uh, the, the, the two brothers.
ChrisHOST
Riley and, why can I not remember the other brother's name?
Bobby BonesSOUNDBITE_SPEAKER
Smiley? No.
David GallagherGUEST
[laughs]
David GallagherGUEST
No, I, I, I do love the-
ChrisHOST
Huey.
ChrisHOST
Riley and Huey.
speaker_3UNKNOWN
Panthers.
AlanHOST
And then you have Riley, who's a bit more contentious.
AlanHOST
He's the sort of like modern, young, hip-hop and rap-obsessed African-American kid who wants to be cool, who wants to carry a gun, who's excited to use Ed Weinstein Jr.'s shotgun on him.
AlanHOST
He wants to have sex.
DJHOST
But let's stick on this one.
DJHOST
So, yeah, in this episode, Riley is trying to go to hang out with Ed Wenzler.
DJHOST
In order to do that, he has to get past Huey.
DJHOST
And, you know, he's like, I'm not going to let you leave this house.
DJHOST
And, you know, Riley's like, I don't want to hang out with my friends.
DJHOST
And they start, dude, this fucking intense ass fight.
DJHOST
It's so crazy.
10 MINS LATER
Will the GreatestHOST
You know, make some