Kyle Crownover is that rare singer-songwriter whose day revolves around neither singing nor songwriting. Rather, he’s in charge of making sure someone else’s songs are heard live: Crownover is Tyler Childers’ longtime tour manager.
But when he gets a break from overseeing one of the most dynamic live shows in music, and making his beloved rescue dog a budding social media star, he has been known to drop a few songs of his own.
“Going from work brain to creative brain can take a long time,” Crownover, who in his spare time also produces albums for artists like Adeem the Artist, tells me. We’re sitting at a picnic table outside a coffee shop on the campus of the University of the South in Sewanee, Tennessee. At our feet is Cheryl, his dog, occasionally yipping at passersby for attention. “I got into tour managing because the idea of just writing songs for other people was terrifying. This lets me keep everything in perspective. When my creative tank is depleted, I can just stay in work mode.”
Crownover has been Childers’ tour manager since 2017, running the show while Childers went from bars and dance halls to arenas and stadiums and turned a single-bus-and-trailer outfit into a caravan of tour buses, semitrailers, and team members. Along the way, Crownover has witnessed the rise the Appalachian music scene — from Childers and Sturgill Simpson in Kentucky to 49 Winchester in Virginia to Charles Wesley Godwin in West Virginia — and as the music from the region has grown into a machine, Crownover has proven to be both a vital and popular cog.
Childers, like most artists who can sustain arena tours, hits the road in fits and starts. In 2025, he played just under 50 shows. Such a schedule builds in downtime, not just for the artist but for the touring party. Over two months late last year, Crownover took advantage of that time and released four singles to streaming services.
The first was November’s “The Flame,” a song he wrote with Parker Millsap. It begins as a stripped-down acoustic blend of folk and blues, about “dimming down the soul” and “pickin’ up the pace,” before building to an electric rock crescendo. “We were just talking about our phones and feeling like they were sucking the life out of us, and we ran with that,” Crownover says of the song’s origins.
In January, he released “Good News,” which he co-wrote with Zach Russell. The two were college classmates at Middle Tennessee State University and are former roommates. Crownover’s upbringing was devoutly religious, and he played music in church well into his 20s. During a period of soul-searching, he turned to Russell as a sounding board. “We were laughing at how the modern evangelical movement talks about good news, but it’s the worst news imaginable,” Crownover says of the roots of “Good News” and the series of late-night talks with Russell that gave rise to the song.
The new music came after Crownover had given Nashville songwriting a fair shot. He had moved to Music City for a time, seeking a publishing deal, and walked away with some songs out of the experiment — ones he packaged as an EP and titled Greatest Hits, Vol. 3. But his big takeaway was clarity, for both himself and his craft.
“These were the first four that I wrote outside of that frame of mind,” he says. “Getting a little personal and specific, and sonically taking chances that I don’t think other people would. It’s got more indie rock and folk stuff than it does pop country.”
Crownover’s versatility, and his involvement in producing and management, stems from wanting to be involved in music at all costs. He was “jiggling any handle” and seeing what doors would open. Circa 2017, he happened upon a Childers concert in Indianapolis and jiggled the only handle that would ultimately matter. He was tour managing Millsap at the time but reached out to Childers’ manager to offer his services. A few months later, Childers’ camp took him up on it.
Cheryl the dog, with Kyle Crownover. Photo: Edwin Keeble*
As Childers and his band, the Food Stamps, have grown, Crownover has had to learn on the fly to keep up.
“I don’t think, on paper, that I’m the best tour manager,” he admits. “Obviously, I wasn’t scouted. I didn’t have the credit before. I didn’t know what I was doing. And on top of that, every single year with Tyler has been drastically different than the last. Nothing about my job is similar to what it was eight years ago. It’s really just, can you deal with change and be resilient? When you’re tired and you’ve been gone for three weeks, can you still go with that flow?”
At least one major organization recently determined that Crownover can indeed go with the flow. In early June, the Country Music Association announced its annual Touring Awards: Childers’ team was a finalist for Crew of the Year, and Crownover was a finalist for Tour Manager of the Year.
“I am the luckiest tour manager alive to get to travel around with a team and band of this caliber,” says Crownover, who goes out of his way to emphasize the awards were a collective honor.
This week, Crownover will find himself wearing his two primary hats. Childers’ ongoing Snipe Hunter Tour hits Chicago’s Wrigley Field on Sunday. But before that, Crownover will take the stage on Friday when he opens for Kory Caudill, keyboard player in Childers band, who has a show at Christ Church in Denver dubbed “Concert for the Human Family” alongside jazz vocalist Imani-Grace Cooper.
When he walks offstage, Crownover will find Cheryl waiting. A pre-show routine in Childers’ dog-loving crew is to bring in animals from local shelters and rescues to pet and play with. It’s a win-win for both the dogs and tour members. When this happened before a 2024 show in Chicago, Cheryl was one of three puppies that showed up in Crownover’s tour office. “I just knew if I looked her in the eye, it would be over,” he says.
When shelter reps told Crownover the dog was expected to top out at 10 pounds, he gave in. Childers signed off on Cheryl becoming a crew dog, and Crownover adopted her on the spot. Her siblings were adopted by other members of the crew, and they keep regular play dates, some of which are documented on Cheryl own Instagram account.
“The amount of positive interactions that I would never have with people — every time I step outside now, it’s smiling and talking to a stranger who’s asking about her,” Crownover says. “Tangibly, she’s changed my life and made it more fun getting to see the world through her eyes. I’m not the most social person, and she breaks down those barriers. One day I counted, and she made me smile 20 times. I was just not smiling 20 times before I got her? That’s worth something.”
Josh Crutchmer is a journalist and author whose upcoming book, Sonoran Sounds, is set for release in March 2027 via Back Lounge Publishing.
