Sheryl Crow: The Girl Least Likely to Be a Rock Star

From Damn Yankees Ensemble to Hometown Hero

This is how small Sheryl Crow’s hometown is:

David Nail’s father was her high school band director.

David Nail

Her mother taught Nail how to play piano.

Trent Tomlinson’s father was her junior high basketball coach.

Trent Tomlinson

And Blackjack Billy‘s Noll Billings’ father was her track coach.

And in that tiny little town of Kennett, Missouri, is one very special school. Kennett High School has inspired so many kids to go on to so many big things, so Crow is going back there for a two-night show to raise money for the performing arts program at the school.

When I talked with Crow about her personal high school experiences back at KHS, I assumed she was that girl — the one who gets all the parts, makes all the shows and is basically the star of everything. I was wrong.


“It’s really funny, because I tried out for the musicals, but I never got a major part,” she said. “If you looked in my yearbook and there was a category for the girl least likely to be a rock star, there would be a picture of me. I wound up being an accompanist for the plays. But it wasn’t until my senior year that I got a small part in the ensemble for Damn Yankees. I wish I could go back and do it all over again and put myself out there more.”

In a way, she is going back again.

This time, she’s going with other KHS alumni for a Kennett Crossroads concert event with Nail, Tomlinson and Billings on Sunday (Jan. 18), an acoustic songwriter’s night at the town’s Opera House, and Jan. 19, a plugged-in, full band show in the school’s auditorium.

“Growing up there, we were in the middle of nowhere,” she said. “And yet, so many great stories have come from Kennett largely due to the great arts program in the school. The four of us artists — who’ve gone on to have visible careers — attribute that to the fact that we had such an incredible safety net from the way we were raised in our town.

“We were raised to believe that music can propel you if you love it and you work at it. But because we’re a small town and it’s not a wealthy community by any means, we’re at a point where we need to update what’s happening there.”

The other reason Crow is heading home for the event is to honor the choir director and mentor who inspired her.

“Viretta Sexton not only inspired us, she actually taught us how to sing,” she said. “How to nurture our instrument. How to be expressive. And she’s still doing that. Everyone who has gone on to succeed has had someone in their life who has told them that they can excel at what they dream of doing. Viretta was that person for so many of us.”

Crow said her sons Wyatt, 7, and Levi, 4, are looking forward to the trip back to Missouri. And while they may be too young to appreciate the arts in the big picture, it sounds like they appreciate the arts in their own way.

“Their favorite thing to do every night before bed is what we call Dance Party,” she said. “They get to play whatever songs they want. This sounds ridiculous, but their favorite song to dance to is my song ‘Shotgun.’ They’ll play it over and over.”

Alison makes her living loving country music. She's based in Chicago, but she's always leaving her heart in Nashville.