“Rich Men Dress Down, Poor Boys Learn To Dress Up” – Charley Crockett On His Journey From The Streets To The Big Stage

Charley Crockett country music
Ryan Vestil

Tomorrow is the day that Charley Crockett drops his 14th studio album, $10 Cowboy

The South Texas native has come a long way since his days performing on street corners, and the smooth twang of the cowboy has traveled all over the world, taking his silky smooth honky tonk voice to every stage imaginable.

Crockett appeared on Good Morning America to promote the last single he released before the album’s release, “Solitary Road,” and also briefly spoke on how he has climbed the ladder to get to where he is today.

Kicking off the short interview, the host comments on Crockett’s look, which is a massive part of his recognizable brand. Crockett notes that it was not always this way but clearly has embodied the “look good, feel good” motto over the years.

“Rich men dress down, poor boys learn to dress up.”

With headlining some of the biggest festivals this year, Crockett remains humble. He just feels lucky to have places that want him to grace their stage.

“I got these agents that just throw darts at a map…they do. They just throw them at the map. I used to think about it a lot. But you know, you just look at me, and you can see the butterflies coming out of my stomach even now, so I really don’t think past today. You know, it’s better to do it that way. 

I’m doing places like The Greek in L.A. and Red Rocks outside of Denver, and I can tell you as a street player, that’s a pretty good corner to be standing on.” 

After hearing how grateful he is to be where he is now, the GMA host stepped aside and let his talent speak for itself as she stuck up the intro for “Solitary Road.”

Charley Crockett is THE real deal. I can’t wait to blast $10 Cowboy in its entirety tomorrow.

A beer bottle on a dock



A beer bottle on a dock