Sturgill Simpson has undeniably carved a unique space for himself in the contemporary music landscape. While he might not be defined by mainstream accolades, his impact on country music and beyond over the last decade is undeniable. Following his debut album High Top Mountain in 2013, his sophomore release, Metamodern Sounds in Country Music (2014), resonated deeply, signaling a potential resurgence of traditional country sounds.
However, Simpson is an artist who defies easy categorization. By 2016, with the release of A Sailor’s Guide to Earth, he explicitly stated, “I just don’t see myself as a songwriter or a country singer or any of those things anymore.” Then came 2019’s Sound & Fury, a bold turn towards gritty, hard rock. Despite these sonic explorations, Simpson’s roots in exceptional country music remain a cornerstone of his artistry.
Across his diverse discography, Simpson has crafted a wealth of compelling songs, spanning from poignant country ballads to infectious, soul-infused rhythms. Even his bluegrass reinterpretations in Cuttin’ Grass, Vol. 1 and Vol. 2 (2020) showcase the versatility of his songwriting. Narrowing it down is a challenge, but these ten tracks represent some of the finest examples of Sturgill Simpson’s musical genius.
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- Long White Line
If mainstream country radio ever seemed within reach for Sturgill Simpson, it would have been with “Long White Line.” This track embodies the essence of a classic country song, solidifying the frequent comparisons to the legendary Waylon Jennings. Its traditional structure, coupled with Simpson’s distinctive vocal delivery, makes it a standout example of his more conventional country sound.
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- Brace for Impact (Live a Little)
“Brace for Impact (Live a Little),” the lead single from A Sailor’s Guide to Earth, marked a significant sonic departure for Simpson. Moving away from his more overtly country origins, this song introduced a new dimension to his music. Driven by a pulsating bassline and textured, funk-laden guitars, “Brace for Impact” demonstrates Simpson’s willingness to experiment and push genre boundaries while maintaining a captivating musicality.
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- It Ain’t All Flowers
“It Ain’t All Flowers” is a track that masterfully blends introspection with a slightly unsettling, psychedelic atmosphere. Simpson delves into brutally honest self-reflection, exploring themes of self-loathing and disillusionment. The song’s 1960s psych-country vibe creates a unique sonic backdrop for his raw emotional honesty. While the recorded version is impactful, Simpson’s live performances of this song amplify its intense emotional core, making it a truly visceral experience.
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- In Bloom
While technically a cover, Sturgill Simpson’s rendition of Nirvana’s “In Bloom” has become as iconic as the original in its own right. By stripping away the grunge elements of the ’90s anthem, Simpson reimagines the song as a tender and thoughtful exploration of masculinity. The sparse arrangement, featuring subtle horns reminiscent of the late ’50s and dreamy piano melodies, combined with Simpson’s hauntingly soft vocals, elevates this cover to something far greater than a simple reinterpretation.
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- You Can Have the Crown
As a proud Kentucky native, Simpson pays heartfelt tribute to his roots in “You Can Have the Crown.” This song serves as an homage to the men in his family who dedicated their lives to the perilous work of coal mining. Far from romanticizing the industry, Simpson paints a stark and realistic picture of the coal mining industry’s impact, both the work itself and its decline, on his home state and its communities. It’s a powerful reflection on heritage and hardship.
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- Oh Sarah
A Sailor’s Guide to Earth is deeply personal, conceived as a musical letter to Simpson’s newborn son. However, “Oh Sarah” stands as a poignant exception within the album’s thematic focus. This tender ballad, often performed by Simpson solo on a stool without his guitar, delves into the complexities of love, heartache, and the guilt associated with being away from family while pursuing a touring musician’s life. This trifecta of emotions resonates deeply, making “Oh Sarah” a truly heart-wrenching and relatable song.
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- Living the Dream
Considering Sturgill Simpson’s near path to a life-long career with the railroad, “Living the Dream” carries a particularly resonant irony. This track appeared on an album that was entirely self-funded, a project with initially uncertain prospects of widespread success. “Living the Dream” encapsulates the unexpected journey Simpson embarked on, transitioning from a railway worker to a celebrated country music artist, highlighting the unpredictable nature of life and dreams.
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- Keep It Between the Lines
With A Sailor’s Guide to Earth, Simpson challenged and redefined audience perceptions of his artistic identity. “Keep It Between the Lines” exemplifies this evolution. Jazzy, funky, and imbued with timeless wisdom, the song offers the kind of life lessons that resonate across generations. It’s the type of song that carries a paternal warmth, filled with advice you might wish you had received from your own father during your formative years.
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- Water in a Well
While Metamodern Sounds in Country Music propelled him into the spotlight, High Top Mountain from 2013 arguably remains Sturgill Simpson’s most dedicatedly hard-country album. “Water in a Well” is a quintessential heartbreak song, steeped in classic country sorrow. The track is enriched by blues-infused piano melodies and soulful steel guitar, creating a rich and evocative soundscape for its tale of lost love and regret.
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- Turtles All the Way Down
“Turtles All the Way Down,” the opening track of Simpson’s breakthrough album, Metamodern Sounds in Country Music (2014), serves as an encapsulating introduction to his multifaceted artistry. Part psychedelic exploration, part traditional country ballad, this song perfectly captures the breadth of Simpson’s creative range and artistic philosophy. Few songs so effectively showcase the unique blend of genres and perspectives that define Sturgill Simpson’s music.
What Sturgill Simpson Song Resonates With You?
We encourage you to share your personal favorite Sturgill Simpson song in the comments below! Let us know which track speaks to you the most and why.
