Caleb Pressley
speaker
202 appearances
1 recordings
1 series
first heard May 2025
last heard May 2025
Caleb Pressley’s voice in public audio — every appearance, attributed to the second.
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recordings per month · last 12 monthsNo recordings in the last 12 months.Older appearances are listed below; set an alert to hear about the next one.
Appearances
We just did Morgan Wallen. I don't know when this comes out, but we did Morgan yesterday. That'll come out this weekend, so I don't know if this is coming out.
We just did Luka. Oh, Luka, huh? Yeah, bounced from the playoffs right after.
Yeah.
Bad. But, dude, he's still making, I mean, it's hard to feel bad for someone who's making, whatever, $97 million the next two years. But I think he lost out on like $116 million.
Yeah, you'd never have to go back with that amount. You'd never have to see Slovenia again with $116 million. Free at last. Free at last.
No, it's been good. I've enjoyed. It's kind of the same thing I was doing when I was at Barstool. I mean, it's pretty much exactly the same thing. Just doing Sunday Conversation. Plus, I'm like, I did Drewski's show, which was fun. Just like one-off kind of collaboration.
Yeah, she's from Memphis. Oh, yeah. Yeah, she's great. She's pregnant, too. Is she pregnant? She's pregnant, and a lot of people don't know if it's Drewskies or not. No way. Yeah, I also don't know. I don't think it is. It's probably not. But also, I don't know Drewski that well.
Yeah, I met his parents, and they're both black, and I still have been hearing that.
Yeah. Dude, one of his parents will even be like, I think he's meh.
Dude, he is so, so funny. Oh. He has such a unique... I didn't even really understand until hanging out with him the uniqueness of his humor and sense of humor. Yeah. He has an incredible sense of humor. Like, he can just tell... Even when he was setting stuff up for a show, like, he's just off the cuff. He doesn't like playing shit really, but... The way he would set up things.
He's like, we're just going to go out there and freelance it. Or not freelance it. Go off the top of our heads. But there needs to be this, this to create this tension or whatever he wanted to set up. Shit I had never really thought about before. Just really smart. A good sense of humor.
No, she is right there.
Dude, this show, they had the funniest girls on this show. Yeah, she looks a little bit like Glenn Big Baby, you know? Yeah, pull up a picture of Glenn Big Baby in jail. I want to know how these guys take so many photos while they're in jail.
I went for – we stormed a court. In Connecticut at a UConn game.
And they were upset that we didn't even get to storm it. We were going to try to storm it.
No, it wasn't that one. It was just a basketball game. I think it's a ranked opponent.
No, dude. I thought you had the wrong sport.
You thought Dwayne Wade versus Mike? Dude, I know my court cases. Don't say that. We got arrested. I forgot about that. But we just went to jail for a couple minutes. Oh, yeah. And when we came out of jail, people were outside cheering for us.
Seriously. It was like a movie. We didn't even have it filmed, but it was amazing.
Is that Greta? Yeah. Dude, pull her. I just want to know what age she is. That's really all I want to know.
Showing 21–40 of 202 · page 2 of 11
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