Chris Stapleton is one of the best country singers working today. It's hard not to sound like a broken record but it's true. He manages to break through the artifice of mainstream Nashville while maintaining musical integrity. There's never a moment where I consider whether or not he's trying extra hard for radio play. Moreover, I never reckon that he's simply trying to grift from award shows through making prestige bait and self important records. Rather, his records always strike me as genuine expressions from an earnest, detailed artist.
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Consequently, trying to narrow down the best songs from Stapleton proves to be an arduous process. It's not a matter of volume, he doesn't exactly flood the market every year or so with 30+ songs on an album like Morgan Wallen. Rather, he's just wholly consistent, each record carefully curated with warm, observant stories. But on behalf of Wide Open Country, I tried my best to narrow down the cream of the crop from one of country's best in Stapleton for a Mount Rushmore.
The Four Best Chris Stapleton Songs to Date
"Tennessee Whiskey"
You had to know it would be here. I won't even waste your time acting like there was a chance it wouldn't be here. Occasionally, you have situations where songs reach icon status and it's polarizing in its quality. But "Tennessee Whiskey" really warrants all the love and adoration it has received over the last decade. Stapleton delivers an anthem of a lifetime, where love saves him from oblivion at the bottom of a liquor bottle. She rivals the best highs, the best glasses of brandy, strawberry wine, or Tennessee whiskey alike.
Any other artist risks playing this a little too heavy-handedly, exhausting alcohol metaphors or winking and nudging so we get the point. But Stapleton doesn't indulge in irony or overwrought emphasis. Rather, he lets the heft of his voice do the bulk of the work. When he belts that she's as warm as a glass of brandy, he howls into the night. There's an earnest nature in his singing, like leaving the bar for this magical woman is a modern miracle. Dozens of artists and singing competition contestants have tried their hands at it after its release. Some of them even end up quite good. But I don't think any of them will surpass the Stapleton rendition.
"Scarecrow in the Garden"
Faith can be terrifying. It's a leap of faith where there's no certain way of knowing the truth. But you believe hard enough that it is the truth with the evidence you have. Then, you just try your best to live accordingly. That faith takes the control out of our hands and forces us to deal with the hand life grants us.
Stapleton tracks this well on "Scarecrow in the Garden," a spare, guitar driven ballad that tracks across multiple generations. He zooms in on the family of immigrants from North Ireland that takes over a farm in West Virginia. The first verse emphasizes prayer, that through faith in God, the weather will treat them kindly as they adopt the farm and grow as a family. Maybe his bet will pay off. The second verse sees the youngest son take over while the farm is prospering and the rest of the family move on with their lives.
However, Stapleton dangles this suffocating tension over the chorus. The good is omnipresent, but so is the potential for pitfalls. The faith isn't enough to save you from Lucifer masquerading as a 'scarecrow in the garden.' He still strips you of your positivity until you feel helpless. All you can do is manage how you react to trials and tribulations.
That's what makes the closing stretch of the song especially haunting. Stapleton sings in the final verse, "The fields ain't what they once were, the rains just seem to flood. And I've been thinking about that river, wondering how it turned to blood." The son in the song did everything right and yet, the farm still has seen its better days. Not to mention, he only took over the farm because no one else was around to keep it. This wasn't his dream. This was his obligation.
Stapleton leaves the son's fate in the air during the outro. He sits there with a bible and a pistol in his hands. Does he let God give him purpose after his life fell apart? Does he roll the dice on faith amidst a Job-like run of bad luck? Or does he take matters into his own hands with the gun and give up? These questions aren't answered and it doesn't judge how you respond. The faith is commendable but you see the hand the son is dealt and you can't help but empathize with his position. It's truly masterful writing from Stapleton and company, forcing you to grapple with the idea that faith might not always be enough to keep going.
"Weight of Your World"
This was the last spot on the list and it was hard to narrow down a song from this album. Higher remains a stellar effort in a 2023 loaded with great country music. I seriously considered "What Am I Gonna Do," a devastating contemplation of grief to start an album. But "Weight of Your World" takes the cake in its tenderness, Stapleton acting as the voice of reason when everything seems to fall apart. "Give me your darkest hour, give me your deepest fear. Just give me a call and I'll be here," he reassures.
"Starting Over"
I'm a sucker for songs about home. Oftentimes, it's easy to get caught up in the cliche, how home is where the heart is and the hokey aspects of it all. Stapleton really manages to sell it here though, bypassing the PG-rated family road trip guitars for an intimate vignette about how the obstacles are worth overcoming. My dad always quotes Tom Hanks in a League of Their Own, saying "If It wasn't hard, everyone would do it. The hard is what makes it great." That sentiment echoes here but it's how he amplifies togetherness amidst turbulence. When Stapleton croons, "I can be your lucky penny
You can be my four-leaf clover," the crushing anxiety of starting from scratch doesn't feel nearly as titanic.
