Chris Stapleton: Inside the Mind of Country Music’s Soulful Star

January 22, 2026 Chris Stapleton

Chris Stapleton recently sat down with Dax Shepard and Monica Padman for a rare, in-depth interview on the popular podcast Armchair Expert. Recorded on location in a barn in Nashville, the Grammy award-winning singer-songwriter opened up about his journey from a Kentucky coal miner’s son to becoming one of the most respected voices in music history.

From his early days writing hits for George Strait and Adele to the legendary CMA performance with Justin Timberlake, here is a comprehensive breakdown of what Chris Stapleton revealed on Armchair Expert.

Early Life: Coal Mines and Valedictorians

Stapleton’s backstory is as gritty as his voice. Born in Staffordsville, Kentucky (population approx. 2,625), Stapleton grew up in a family deeply rooted in the coal industry. His father was an electrical engineer who operated underground coal mines, a volatile business that shaped Chris’s work ethic.

Contrary to the “roughneck” image often associated with outlaw country, Stapleton revealed a surprising academic background:

Valedictorian: He was one of the valedictorians of his high school graduating class of 250 students.
Athlete: He played linebacker in high school, describing football as an “organized street fight.”
Education: He attended Vanderbilt University (the “Harvard of the South”) for engineering but dropped out because he “hated it,” later attending the University of Kentucky for business before finding his way to music.

The Move to Nashville: A Songwriting Prodigy

Stapleton moved to Nashville in 2001, and his success story is an anomaly in Music City. While most artists struggle for years, Stapleton secured a publishing deal within just seven days of arriving in town.

For over a decade, he worked as a “salaried songwriter,” writing six number-one hits for other artists. He wrote songs for:

Kenny Chesney
Luke Bryan
George Strait
Adele

Stapleton discussed his low-ego approach to songwriting, noting that he was happy “making up things on a guitar” in a room while others got the fame. Interestingly, his hit song “Higher” (released on his 2023 album) was actually written 24 years ago during his first year in Nashville.

The SteelDrivers and Bluegrass Roots

Before his solo career exploded, Stapleton fronted the bluegrass band The SteelDrivers. Started casually with songwriter Mike Henderson to play at VFW halls, the band eventually signed a deal with Rounder Records.

Stapleton revealed the peculiar reason he left the band: a bandmate developed a severe fear of flying, which limited their ability to tour. Combined with creative differences, this pushed Stapleton toward a new path.

The Story Behind Traveller

The album that changed everything, Traveller, was born out of grief and a road trip. Following his father’s death in 2013, Stapleton’s wife, Morgane Stapleton, bought him a 1979 Jeep Cherokee in Phoenix, Arizona.

During the drive back to Nashville, with the sun coming up near Gallup, New Mexico, Stapleton wrote the title track “Traveller.” He credits Morgane, who was also a songwriter with a deal on RCA, as his “higher power” and an essential part of his creative process.

The Justin Timberlake CMA Performance

Dax Shepard asked about the moment the world woke up to Chris Stapleton: the 2015 CMA Awards performance with Justin Timberlake.

Stapleton revealed that he was the one who called Timberlake. They had met previously at a birthday party in Montana where Stapleton played a private set for Justin in a cabin with no electricity. When the CMAs offered Stapleton a slot, Morgane insisted he call Justin.

Timberlake agreed immediately but made a bold request to producers: they needed 8.5 minutes of airtime, an eternity in live television. The producers agreed, and the performance of “Tennessee Whiskey” and “Drink You Away” launched Stapleton’s solo career into the stratosphere overnight.

Chris Stapleton’s Personal Philosophy

Throughout the Armchair Expert episode, Stapleton offered a glimpse into his personality:

He Seeks Silence: With five kids at home, he actively looks for silence to let creative ideas “come down through the antenna.”
Perfectionism: He admits to struggling with deadlines and overthinking, driven by a desire to avoid mistakes.
Sobriety and Vice: While Shepard is sober, they discussed addiction. Stapleton joked he is a “9 out of 10” on the addiction scale by nature but manages it. He enjoys whiskey and recently launched his own brand, Traveller Whiskey, in collaboration with Buffalo Trace.
Fame: He dislikes the “celebrity” aspect of his job, preferring to hide behind his beard and hat. He noted that he enters interactions with fans with anxiety, wanting to make sure he doesn’t let them down.

What’s Next for Chris Stapleton?

Stapleton is currently on his All-American Road Show tour. While he admitted to Dax that he is currently at a “crossroads” regarding what fuels his creativity next, he remains committed to delivering 100% to his fans every time he steps on stage.

You can listen to the full episode of Armchair Expert with Chris Stapleton on Spotify or wherever you get your podcasts.