Caleb Pressley Once Tried To Invest In Luke Combs Before He Got Big, But Didn’t Like His Songs – That All Became #1 Hits

Luke Combs country music

Little did I know that Luke Combs, and Barstool personality Caleb Pressley went to high school together, and were friends.

The two went to A.C. Reynolds High School in Asheville, North Carolina, which also happens to be the same high school Chase Rice went to as well.

However, Combs was a senior when Pressley a freshman, but the two played on the football team and became friends through that.

But it wasn’t because they were both stars who played every snap together (Pressley ended up being pretty dang good by his senior year, as he went on to play quarterback at North Carolina), it was because they both rode the bench and had plenty of time to conversate.

Pressley talked about that friendship when he made an appearance on Theo Von’s podcast, where he hilariously recalled:

“Me and Luke went to high school together. He was an offensive lineman, he was a senior when I was a freshman, so I played on varsity as a backup quarterback, and then he was a senior offensive lineman.

So he didn’t play much, and I didn’t play at all, and so we would sit and talk to each other on the sidelines… It’s like the guys who know they’re not getting in so they’re getting really comfortable, like digging into their heels and having a good conversation, like that’s what we were doing.”

Luke then went off to App State, where he began to pursue music by playing local venues and posting videos to Facebook.

And for Pressley, his father passed away when he was very young, so when he turned 21, he got $40-$50,000 sent straight to his bank account from Social Cecurity.

And at 21 in college, he didn’t know what to do with all of that cash…

So after seeing somebody from their high school already make it in music with Chase Rice, he had the grand idea of investing in Luke’s career before it took off:

“I hit up Luke, and was like ‘What can I do, I want to invest this…’ 

I was like man I’ve got this money I’m trying to blow, and I was like ‘I’d really like to figure out a situation to invest in your career dude. You can do something you just need some money.'”

Combs ended up sending Pressley a few songs he was working on, and hilariously enough, Pressley wasn’t a huge fan:

“I listened to them and I’ve got this cocky 21-year-old, I’m not being cocky, but you know you just think you know everything, and I’m like ‘Ah well I don’t know.’

I sent him back some notes and was like ‘I like this one, we could do this.’…

Long story short nothing ever happens because it’s impossible to just give someone money, and like what if I got like 10% of his career earnings? I wouldn’t be here I know that.'”

And those three songs he wasn’t a fan of?

One was “When It Rains It Pours,” and all three ended up becoming #1 hits for Luke.

Ya hate to see it.

You can check out the full conversation here:

A beer bottle on a dock



A beer bottle on a dock