Holler Country Music

The Best Charley Crockett Songs

December 6, 2022 11:48 am GMT
Last Edited June 21, 2023 11:39 am GMT

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Charley Crockett is a special artist.

Across his 12 albums, including non-original tribute records, he’s managed to write timeless music and deliver consistently exquisite vocal performances.

His creativity knows no bounds - he sings from the heart, and you feel it in every single word.

Here is Holler's list of 15 of the best Charley Crockett songs:

Sony of Davy | 2016

I'm Not Afraid

Despite all his past miseries, Crockett is unafraid to let love back into his heart: “I know that I’ve got to be stronger”. He dusts his love-stitched declaration with light percussion and organ, poking ever so gently through the delicate nature of his words. What is life if not for love.

Son of Davy | 2018

The Sky'd Become Teardrops

With anguish pumping in his veins, the heart-on-his-sleeve troubadour calls for thunderous, billowing clouds to gather on the horizon. “And I would die,” he proclaims.

Guitar chugs along, guiding the rhythm section to wrap heart-sick lyrics with barbed wire. And the thing about rain, it’s wonderfully cleansing.

Son of Davy | 2022

I'm Just a Clown

Crockett brings classic R&B to his usual style on this cut from The Man From Waco. Horns and electric guitar drive the arrangement, as he brandishes the sad clown metaphor to expose his own hollowed-out vulnerabilities.

“I’m just a clown / That’s what they say,” he lets out a chilling howl. Its groove is sticky and sweet, a contrast against the emotional edge.

Charley Crockett | 2015

Drivin' Nails in My Coffin

Crocket has endured his fair share of heartache. With the pain there comes waves of regret, mixing with endless drinking from the beer tap. He’s just “drivin’ nails in my coffin over you,” he cries into his glass.

It’s not enough that the break-up did a number on him; it’s the danger habit of spinning on a bar stool that does him in.

Son of Davy | 2022

Trinity River

Sultry trumpet leads this soulfully spun arrangement. Originally found on his debut album, A Stolen Jewel, he returns to that creative well for The Man from Waco, giving it a polish for a far groovier take.

Initially, the song depicted the aftermath of a record deal gone bad, and years later it carries greater significance. By the look of things, he did quite well for himself.

Son of Davy / Thirty Tigers - 2020

Welcome to Hard Times

“I hope you’re feeling welcome to hard times”; Crockett humors the prevalence of sin and corruption, on the title track to his 2020 album. Saloon keys twinkle with a bluesy undertow, also present with the slinky, spinning rhythm section.

Crockett’s vocal slides and simmers on the melody, inviting the listener to engage with “sinning” well “before you go.” It’s the sort of rugged living that’s made for the movies.

Son of Davy / Thirty Tigers | 2022

Borrowed Time

Opening The Valley, ‘Borrowed Time’ lingers on the lips as an admission that love is fleeting, and there’s no stopping its inevitable crash.

Crockett’s inability to hold onto a quickly vanishing romance funnels into the propulsive percussion, fiddle and hand claps, a deceptively cheery arrangement to soothe the senses. “I want to be free,” he confesses.

Son of Davy / Thirty Tigers - 2020

The Man That Time Forgot

Crockett is just a wanderer, a man lost in the sands of time. Instead, he meanders through life begging to be heard. But he can’t stop any of it from happening. The clock ticks faster every minute, leaving him alive only in forgotten memories.

Sony of Davy | 2016

What's Made Milwaukee Famous

Crockett has always been an expert vocalist, and ‘What’s Made Milwaukee Famous’ remains a prime showcase for his talents. The anguish drapes across every syllable, piercing and heartfelt. His baby is long gone, and he finally owns up to his wandering ways. He can never stay put, even in love.

Charley Crockett | 2015


​​Terribly heartbroken, Crockett bares his heart and soul like some wretched funeral march. Organ plays as it does in hymnals, buffering the story with emotional sheen. It only shimmers when his voice is lifted out of such despair and given a second life. New love eventually takes root, and he blooms once again.

Son of Davy | 2021

Lies and Regret

A song that could have been a Hank Williams b-side, this Music City USA cut depicts the slow march to death as it relates to the burning out of a relationship.

“I'm graveyard whistling, though I'm not quite undеr yet,” he shrugs. He’s been through it all, so the Grim Reaper is the least of his worries.

Son of Davy | 2022

Time of the Cottonwood Trees

Time is ever ephemeral; of no real consequence, if you think about it.

With ‘Time of the Cottonwood Trees’, Crockett reflects back to a lover who’s since floated out of his life and into another. He admits that “it’s hard to figure what life really means,” so he collects all the memories he can. That’s all that really matters.

Son of Davy / Thirty Tigers - 2020

The Poplar Tree

Crockett outruns heartache, but it eventually catches up to him. A story song, ‘The Poplar Tree’ tells the tragic tale about a man who gets into a gun fight with another and ends up being hung from a poplar tree.

“I was holding my head up”, his last haunting words seem to echo across the land.

Son of Davy | 2022

The Man from Waco

Throughout The Man from Waco, Crockett explores ideas about physical and spiritual deaths, coming to a climax with the title track. “A moment of burnin' anger can curse the livin' through the days,” he sings, bookending a sorrowful tale of revenge and accidental murder.

Down to Crockett’s vocal, there’s a devastating haze clouding the sky.

Son of Davy | 2021

The World Just Broke My Heart

The world outside nearly crushes his spirit. “It blew my mind / And took my religion / One mistake at a time,” he cowers into a dive bar so as to avoid the flurry of news headlines and tragic murders. Suffocating sorrow infects the world, one sorry soul at a time, and Crockett will be damned if he’s going to let it get to him, too.

Listen and subscribe to Holler's The Best Charley Crockett Songs playlist below:


For more on Charley Crockett, see below:

Written by Bee Delores
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