Chris Stapleton, Before the Spotlight: How a Bluegrass Side Project, a Few “Perfectly Good Songs,” and a Fear of Flying Helped Shape a Superstar
- All Country News
- 9 hours ago
- 4 min read
Before Chris Stapleton was a household name, before his voice became one of the most unmistakable instruments in modern country music, he was just a Nashville songwriter with a stack of songs that didn’t quite fit anywhere else.
On a recent appearance on Armchair Expert, Stapleton pulled back the curtain on a chapter of his life that feels almost mythic now: the accidental birth of The SteelDrivers, the bluegrass band that would quietly sharpen his artistry, bruise his bank account, and set him on a collision course with a career he never planned to have.
It all started, as the best bands often do, “just for fun.”
Stapleton recalled writing with the late Mike Henderson, a revered blues guitarist and session ace whose résumé ran deep through Nashville’s back rooms and recording studios. Henderson, a self-described guitar slinger with a taste for the gritty and traditional, shared Stapleton’s love of bluegrass. Between them, they had a pile of dark, rootsy songs — murder ballads, heartbreakers, and Appalachian ghosts — that had no place on commercial country radio.
“We had these perfectly good songs sitting around going to waste,” Stapleton said, almost shrugging at the idea that those songs would eventually change his life.
The original goal wasn’t fame, records, or even a tour bus. Henderson simply wanted a weekly gig — maybe at a VFW hall — a place to play music with friends and stretch out songs that didn’t belong anywhere else. They gathered a few elite session musicians, started playing standards, and then slowly folded in their own material.
Then something unexpected happened: people showed up.
Then more people showed up.
Then Rounder Records called.
The SteelDrivers’ rough-hewn, soul-deep bluegrass found an audience that Stapleton never saw coming. The band released two albums, earned Grammy nominations, and built a cult following. From the outside, it looked like a breakout moment.
From the inside, it felt like a financial faceplant.
“I was losing money playing that,” Stapleton admitted, explaining that time on the road with the band meant lost songwriting income — the very thing he’d moved to Nashville to do in the first place.
Still, he wouldn’t trade it.
“I think that made me a better writer doing that,” he said. “I learned how to be in a band in that band.”
For a man who never intended to be a frontman, The SteelDrivers became his crash course in collaboration, humility, and musicianship. Everyone in the group was a pro. Everyone pulled their weight. And Stapleton, almost accidentally, became the voice at the center of it all.
“I moved to Nashville to be a songwriter,” he said flatly. “At no point did I go, ‘Okay, we’re switching gears. I’m only writing for me.’ It just happened.”
That theme — of things simply happening to him — runs like a quiet undercurrent through Stapleton’s story.
Even his exit from The SteelDrivers reads like a folk tale.
One of the band members developed a fear of flying. Stapleton and the rest of the group disagreed on how to handle touring logistics. The band chose a different direction.
“Technically, yes,” he said with a wry laugh, when asked if he was fired. “That’s technically the truth.”
It stung. Of course it did. But Stapleton also felt the band wasn’t steering toward the future he believed in.
“So I was like, ‘Okay, well… I’ll do something else.’”
What he did next, of course, was form another band, keep writing, keep showing up, and eventually become Chris Stapleton — the artist, not just the songwriter.
Along the way, he’s kept an almost monk-like relationship with creativity. He doesn’t fear the blank page. He doesn’t panic about deadlines. In fact, he openly distrusts them.
“I prefer something to be right over it being done,” he said.
He treats songwriting less like a job and more like a ritual: walk into a room, put the antenna up, and see what falls out of the sky. No pressure. No clock. No panic.
And despite his superstardom, Stapleton still seems more at home in the writer’s room than on the red carpet.
“I really love the role of getting in a room with somebody and writing for their thing,” he said. “What are we going to do today?”
It’s a startlingly humble philosophy from a man who now sells out arenas.
But maybe that’s the point.
Stapleton never chased the spotlight. He chased songs. The spotlight just caught up to him later.
In the end, his SteelDrivers years weren’t a detour. They were a forge — shaping his voice, sharpening his instincts, and teaching him how to be part of something bigger than himself.
It began with a few “perfectly good songs” and a weekly gig that was supposed to go nowhere.
It ended with the making of a master craftsman — one who still, to this day, insists he’s just showing up.
Watch the full interview below!
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