When Clay Humphrey talks about music, it’s clear he’s got an appetite for discovery. He stopped by KHOL in between lessons at the Teton Music School, where he spends most of his time when he’s not performing with funk-rock group Cache Funk. His Gibson acoustic guitar accompanied him into the studio, a first-time experience for the Jackson native.
Though he’s never had a formal music lesson, Humphrey’s musical career began at the Bar J Chuckwagon, a nightly musical theater dinner performance that his family started back in 1977. When the space shuttered and sold in 2021, the 29-year-old had to reform his vision of what the Jackson music scene really looked like.
He knows the importance of lucrative country covers to local nightlife. But he prefers a quieter, more intimate setting where folks can actively listen. In November 2025, Humphrey got involved with the Hootenanny, a long-running weekly showcase of local songwriting talent reminiscent of the Grand Ole Opry. There he’s found the perfect place to play.
“I don’t love music just being a background element of people’s lives. That’s not how it works for me. If there’s music going, I want to pay attention to what’s happening on stage,” said Humphrey during the live in-studio performance during KHOL’s Intermountain Best show.
And that attitude has paid off.
Humphrey is the 2026 champion of the Wyoming’s Singer-Songwriter Competition, which brings musicians from across the Cowboy State to show off their chops and collaborate. His unreleased tune, “The House on Cherry Street,” was inspired by the rising housing costs in Jackson and ultimately won him the contest.
“There’s folks throwing their money away just to have a place to sleep, ’cause the houses down on Cherry Street are just assets to keep,” Humphrey sings the second verse of the song.
The competition boosted Humphrey’s confidence as a musician and songwriter, reassuring him that self-doubt is common among artists.
“It’s definitely not the kind of thing that I’d have done a year ago. I’m a fairly quiet dude,” he said.
He approaches the craft of songwriting thoughtfully, drafting far more songs than he keeps. Some he workshops for years, others just flow. Earlier this year, he participated in the global February Album Writing Month, a project aimed at writing 14 songs during the short month and helping artists stay motivated.
“You are not going to sharpen a knife by running a whetstone over it once; you have to do it over and over,” Humphrey said.
Harkening back to nightly gigs with his family, he treats live, high-stakes performance just as seriously.
In this summer’s pit band for Off Square Theatre’s production of the musical “Something Rotten,” missing a mark could throw off the entire show. But when everything lands, that’s satisfaction.
The multi-instrumentalist finds the most joy, though, in wandering and improvising, a common element of Cache Funk. He claims his Rolodex of guitar licks derives primarily from bluegrass and artists like Chris Thile. He also draws on elements of prog-rock legend Eric Johnston with his technical “shredding” over expansive sounds that manage to fit within fairly straightforward chord progressions.
Fans can catch Clay performing at the Hootenanny on Mondays or follow his journey on Instagram and YouTube @yourhumphrey. His debut EP is expected soon, marking the next chapter in a career that’s only just beginning to take flight.
Listen above for KHOL’s full conversation and live performance with Clay Humphrey.
Support for this arts and cultural coverage comes from the Wyoming Arts Council.
