He may not have a shelf full of trophies, but there’s no denying that Sturgill Simpson is one of the hottest names and buzziest acts to emerge in country music within the past decade. The singer-songwriter's 2014 album Metamodern Sounds in Country Music -- his sophomore album, following 2013's High Top Mountain -- was, upon its release, regarded as a sort of bellwether that traditional country was making a comeback.

Simpson's 2016 release, A Sailor's Guide to Earth, changed directions a bit: "I just don’t see myself as a songwriter or a country singer or any of those things anymore," Simpson said a few months prior to the record's debut. Then, 2019's Sound & Fury went full-on fuzzy, grungy rock -- but that doesn’t mean Simpson hasn’t made a whole lot of great country music along the way.

Simpson's catalog contains many excellent songs, ranging from hard-country ballads to funky, soul-inspired grooves -- and, with 2020's Cuttin' Grass, Vol. 1 and Vol. 2, bluegrass versions of his catalog -- but the following 10 tracks are among his best.

  • 10

    “Long White Line”

    From: 'Metamodern Sounds in Country Music' (2014)

    If Simpson ever had a shot with mainstream country radio, it would’ve been with “Long White Line.” As classic a country song as you’ll find, this is where Simpson really earns the frequent comparisons to Waylon Jennings.

  • 9

    "Brace for Impact (Live a Little)"

    From: 'A Sailor's Guide to Earth' (2016)

    Released as the first single from A Sailor’s Guide to Earth, “Brace for Impact (Live a Little)” introduced an entirely unique side of Simpson, one that sounded a whole lot less country than much of his prior work. Still, there’s no disputing the appeal of this song's throbbing bass line and fuzzy, funky guitars.

  • 8

    "It Ain't All Flowers"

    From: 'Metamodern Sounds in Country Music' (2014)

    As trippy as it is a little depressing, “It Ain’t All Flowers” is a brutally honest track. Here, Simpson is equal parts introspective and self-loathing, all wrapped in a 1960s-inspired psych-country vibe. The recording is great, but Simpson’s live performances of this song really drive home its almost furious emotional intensity.

  • 7

    "In Bloom"

    From: 'A Sailor's Guide to Earth' (2016)

    Okay, it’s not technically a Simpson song, but Simpson's cover of Nirvana’s “In Bloom” is as iconic as the original. Removing the original track’s grungy edge, Simpson transforms this '90s classic into a tender meditation on masculinity; the sparse arrangement, flecked with late-'50s horns and dreamy piano, pairs with Simpson’s softly haunting vocals for a cover that’s a whole lot greater than the sum of its parts.

  • 6

    "Old King Coal"

    From: 'High Top Mountain' (2013)

    A native Kentuckian, Simpson pays homage on this track to his roots and the men in his own family who worked in the coal mines to provide for their families. There’s no romanticism here; instead, Simpson provides a stark outline of what the mining industry (and its decline) has done to his home state and the people who live there.

  • 5

    "Oh Sarah"

    From: 'A Sailor's Guide to Earth' (2016)

    A Sailor’s Guide to Earth is an album dedicated to and written for Simpson’s infant son, with one major exception: the endlessly tender “Oh Sarah.” On this ballad, frequently performed by Simpson while sitting on a stool without his guitar, the artist explores heartache, love and the guilt that he feels being away from his family while traveling around the country to play music -- a trifecta that is almost guaranteed to tug at the heartstrings.

  • 4

    "Living the Dream"

    From: 'Metamodern Sounds in Country Music' (2014)

    Considering that Simpson almost ended up a lifelong employee of the railroad instead of a bona fide country star, “Living the Dream” is a track that makes a whole lot of sense. But let us remember: It came on an album that was entirely self-funded, one that Simpson had no clue would be one of the most massive records of its release year.

  • 3

    "Keep It Between the Lines"

    From: 'A Sailor's Guide to Earth' (2016)

    With A Sailor’s Guide to Earth, Simpson flipped everyone’s notion of who he was as an artist completely on its nose, and "Keep It Between the Lines" is jazzy, funky and packed with plenty of the old-school wisdom that the world could use a whole lot more of these days. It’s the kind of song that you wish your own dad had written to you when you were a kid.

  • 2

    "Water in a Well"

    From: 'High Top Mountain' (2013)

    He may have shot to fame with Metamodern Sounds in Country Music, but 2013’s High Top Mountain is Simpson’s most hard-country effort to date. “Water in a Well” is a classic sad old heartbreak song, infused with a heavy dose of bluesy piano and plenty of soulful steel guitar.

  • 1

    "Turtles All the Way Down"

    From: 'Metamodern Sounds in Country Music' (2014)

    The opening track to Simpson’s breakout album, 2014's Metamodern Sounds in Country Music, “Turtles All the Way Down” is sort of like a crash course in Simpson. Part psychedelic fantasy, part old-school country ballad, there are few songs that better capture Simpson’s creative range and artistic ethos.

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