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Ever since time began, country music has always relied on a peculiar brand of recalcitrant outsiders to reshape it and give it a good kick up the arse whenever it needed it most.
As much at odds with the genre as he was in thrall of it, Sturgill Simpson was always destined to be one such outsider; refusing to play by the rules or suck up to the establishment, he was the unlikely saviour of country traditionalism when he emerged in 2013 with his debut album, self funded and recorded with the at-the-time relatively unknown producer Dave Cobb.
Since then he’s released five albums of original studio material under his own name and one as Johnny Blue Skies, as well as raided his own back catalogue for two surprise bluegrass albums in 2020.
I’m sure he’d give the very idea of a ranked list of his best songs a hard Paddington stare, but for the rest of you, there are the 15 Best Sturgill Simpson Songs according to Holler.
After promising to only release five studio albums under the name Sturgill Simpson, he stayed true to his word with the release of Passage Du Desir under the Johnny Blue Skies moniker in 2024.
The record itself, produced by Johnny Blue Skies and David Ferguson and recorded at Clement House Recording Studio in Nashville, TN and Abbey Road Studios in London, sounded like the same old Sturgill underneath it all though.
A mix of eighties glossy pop production and outlaw country that sounded like a cross between Waylon Jennings and Robert Palmer, Passage Du Desir was perhaps the first ever "Yacht Country" album. If there had been any singles lifted off the album then 'Right Kind of Dream' would have been the one to take to radio.
Of the new chapter, Simpson explained, “You can turn the page or you can light the book on fire and dance around the flames. You can try to live above hell or you can just go raise some. Here’s to clean livin’ and dirty thinking.”
Sturgill might not be particularly fond of it, but this hi-octane outlaw workout has always been a steady fan favourite.
Sitting on the couch, strung out on weed and pills, Sturgill spends his days watching Dukes of Hazzard and surfing the internet for old cars and guitars he can't afford. On top of the proverbial “shit mountain”, he’s weighing up the pros and cons of selling his soul to the devil.
He re-recorded the song for Volume 2 of Cuttin’ Grass, so maybe he’s warming to it after all.
After releasing the kind of record that makes an entire genre rethink itself, Sturgill switched lanes again with his first for a major label. Stepping away from Dave Cobb, Sturgill picked up the production duties himself on A Sailor’s Guide To Earth; a heartfelt guide to life and living for his son.
The sound was lushly orchestrated and soulful, taking its cues from Fame Recordings and seventies Elvis, with sweeping brass and string sections and explosive country funk breaks. The anti-war album closer ‘Call To Arms’ served as its furious crescendo.
Taken from his debut album High Top Mountain, Sturgill upped the BPM on this rattling train song, as he took a good long hard look at himself and his past mistakes and misdemeanours.
“I got that throttle to ten on the railroad of sin, I'm coming off of the rails and I can't slow it down”, he sings, as the band races to keep up with him.
The video, filmed by Yosuke Torrii, candidly captures Sturgill on tour in Japan, where Sturgill had lived after leaving the navy.
Sturgill takes on ancient philosophy and organised religion in the opening track from Metamodern Sounds In Country Music, invoking the mythological idea of a “turtle world”. While he suggests that mind-altering drugs had positively changed his outlook, “love's the only thing that ever saved my life”.
As for the turtles, Stephen Hawking describes how a well-known scientist once gave a public lecture on astronomy in his book A Brief History of Time.
As the story goes, after the lecture, an old lady at the back of the room got up and said: "What you have told us is rubbish. The world is really a flat plate supported on the back of a giant tortoise." When the scientist asked her condescendingly what the tortoise is standing on, the old lady replied, "You're very clever, young man, very clever. But it's turtles all the way down!"
If Sturgill's rebranding as Johnny Blue Skies needed a musical explanation then 'Scooter Blues' gave the biggest clue to his current state of mind.
His well documented desire to come out from beneath the weight of his own celebrity artist status and to live a simpler life without expectations seemed to inspire the lyrics to this breezy cut of funky tropical rock.
"Think I'll move to an island and turn into vapor," he sings. "Get a scooter and a house on a hill / Fish all day just to fill up the grill Spend my mornings making chocolate milk and Eggos / My days at the beach, my nights stepping on Legos / Gonna wave to the world screaming hasta luego."
A Sailor's Guide to Earth - a loving guidebook to his newly born son that squeezed everything the country singer has learned up until then into a musical handbook to teach him how to live - was unsurprisingly beautiful in places, as Sturgill came face to face with the enormity of life and tried to make sense of it all.
The gorgeous 'Breakers Roar', inspired by Simpson’s short-lived time in the Navy, used the breaking waves as a metaphor for the the circle of life, the passage of time and the push and pull of the universe.
The partly animated video was directed by Matt Mahurin.
Country singers and songwriters have never been afraid to touch on some of the more soft-centred, sentimental subject matters that other genres simply can't reach, and so it is with songs about their furry four-legged friends.
The genre has had its fair share of songs about dogs through the years and Sturgill Simpson's 'Sam' from The Ballad of Dood & Juanita was a fitting tribute to a dead dog that avoided the sappiness of Marley & Me, but left all the emotion in.
Standing out like a sore thumb in the middle of Sturgill’s catalogue is the soundtrack to the dystopian Netflix anime SOUND AND FURY, which he created with Japanese animator Junpei Mizusaki.
An intoxicating mix of electro and country rock that Sturgill described as a "sleazy, steamy rock'n'roll record", this chugging synth-rock stomp sounded like a cross between ZZ Top and seventies glam rockers Showaddywaddy, as Sturgill grumped his way through the downsides of touring and fame.
“Do as I say, don't do as I've done”, Sturgill warns on this blasting country-funk cut from his third album, as he dispenses fatherly advice to his new-born son, urging him to “stay in school, stay off the hard stuff and keep between the lines”.
Other timeless pearls of wisdom included “motor oil is motor oil, just keep the engine clean” and “don't burn two lanterns at the same time”. Got it. Will do.
One of the rare moments of straight up country on Passage Du Desir, ‘Who I Am’ was a tender moment of self reflection and flagellation that could have easily fitted on Metamodern Sounds In Country Music.
"They don't tell you when you're born it's gonna be this way
They don't tell you until you die it's all a sham
They don't ask you what your name is when you get up to heaven
And thank God, I couldn't tell her if I had to, who I am"
Just wait til the TikTokers pick up on this one and send it stratospheric.
Described by Sturgill as being a "metaphor comparing the soothing yet completely addictive and damaging effects of hard narcotic opiates" to organized religion, ‘Living the Dream’ was the lead single from his second album.
In production, it shifted away from the hard country traditionalism of his debut towards a more psychedelic style of soulful country rock. The album received a Grammy nomination for Best Americana Album, as Sturgill became the reluctant popular face of leftfield country, taking over late-night talk shows and finding himself increasingly under the spotlight.
Sturgill looked back to his days in the US Navy for this song from his third album, with lyrics full of in-jokes that you’d need to have actually been in the Navy to understand.
Luckily, for all of us who haven’t, there is a comprehensive Reddit thread that explains where Dam Neck is (the home of multiple training facilities), what a pollywog is (an uninitiated sailor who has never crossed the equator) and what BMFs are (Bad Mother Fuckers).
Surprisingly, it’s still the only country song to reference taking drugs and playing GoldenEye on the Nintendo 64.
After putting out two albums of bluegrass recorded and released during the worldwide covid pandemic, Sturgill took a week out with the intergenerational band of musicians he nicknamed the “Hillbilly Avengers” to cut the bluegrass concept album, The Ballad Of Dood And Juanita.
Released in 2021, the frontier love story took in traditional country, mountain music, gospel and a cappella, with a nod to cowboy songs and the myths of the American West. Upon its release, Sturgill announced it would be “the last Sturgill record”, completing what he sees as a five-album arc that began with High Top Mountain.
Ostensibly just a good old fashioned truck song, Sturgill took the well-worn country trope and turned it on its head as he sang about escaping his past and turning his life around.
He channels the outlaw country sound of Waylon Jennings and Merle Haggard in this driving long haul anthem that pressed the reset button on country music when it came out in 2014.
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