Chris Stapleton’s “Starting Over” Made Me Cry At The Preschool Dropoff Line

Chris Stapleton country music

On my son’s first day of preschool, I didn’t cry… until I started my car and heard Chris Stapleton’s damn, emotional, platinum song, “Starting Over,” on the radio.

I pulled the car out of the driveway and caught my son’s eyes, wide and panicked in the middle of the schoolyard. I looked away quickly. My sister told me it was best that way for the kid. Don’t stretch out the pain of leaving. Just go and let the trained teachers pick up the pieces when your kid falls apart.

She failed to warn me about what to do when I fall apart. And that’s exactly what happened when I heard the perfect song at the perfectly wrong moment.

The Stapleton’s hit me with the opening acoustic guitar and tambourine on the title track of Chris’ Grammy-winning album. I shifted into drive and bit my lower lip.

“You’ve gotta be kidding me, Stapleton. Why now?”

I held it together through two stoplights and eased into a tight right turn. But I couldn’t shake the image of my kid walking away from me into his school, growing up too fast already, and staring out at me with those big, unblinking brown eyes.

And as soon as I hit the second verse, things had gone to pieces in my car.

“This might not be an easy time
There’s rivers to cross and hills to climb
And some days we might fall apart
And some nights might feel cold and dark
But nobody wins afraid of losing
And the hard roads are the ones worth choosing
Someday we’ll look back and smile
And know it was worth every mile”

As Stapleton told NPR’s Noel King back in 2020,

“As you do with songs sometimes, you write ’em and, pull it back out and you listen to it, and maybe it means something else in a different time, which is beautiful,” he says. “That’s what actually gives it life to me.”

When I heard that song in my car at 8:15am on a Monday morning that I’ll never forget, it meant something different. At that particular time, I heard that second verse like it was a message to my son, encouraging him as he embarked on a scary new chapter of his life.

Or maybe it was a message to me, propping me up as I reflected on the ups and downs of three years of parenting and absorbed the crushing emotions that hit you out of nowhere when you realize your kids aren’t babies for long.

Either way, I was a grown man crying in my car. Thanks a lot, Chris.

Any parents out there who need a good cry should queue up “Starting Over” during their kid’s next milestone. It’s a beautiful, living song that just might mean a little something different to you on that particular day.

Thanks a lot, Chris.

A beer bottle on a dock



A beer bottle on a dock