Essentials: The top 10 Sturgill Simpson songs

Image of Sturgill Simpson

Sturgill Simpson comes from a family that has a strong musical heritage, his grandfathers and uncles all playing guitar. His bluegrass heritage was originally evidenced in 2004 with his band, Sunday Valley until he put his musical ambitions aside to work for Union Pacific Railroad. Coming back to music, and after disbanding Sunday Valley in 2012, Simpson released his debut solo album ‘High Top Mountain’ in 2013. Subsequently, in 2020, bluegrass goodness resurfaced with Simpson releasing ‘Cuttin’ Grass Vol 1‘ hotly followed by Vol 2 which treated us to some of his previously released songs interpreted through the lens of this genre. Whilst Union Pacific Railroad may have lost a valuable asset, Simpson himself would seem to have been strengthened by the allure of the six-string: “Looking back on it, now I can identify the points in my life when I wasn’t playing and music and didn’t have that outlet – those were the points when I was most unguided and self-destructive because I didn’t have that channel to get those energies out. I’m a much healthier person when I play music.”

This top ten of Simpson’s songs leans towards live renditions; watching Simpson’s expressions and movements seems to be part of experiencing his work and gives visualisation to some of that anger, cynicism, and swagger that refuses to fit the Nashville mould. Hopefully, you may find what will become some of your new favourites, be reassured that your favourites are already here or be upset your favourites are omitted or be profoundly indifferent to the work of this artist; if the latter two, I can only say I’m sorry.

Number 10: ‘Water in the Well’ from ‘High Top Mountain‘ (2013)
Taken from his debut album, ‘High Top Mountain’, this is a traditional country tale of heartbreak, pain and loss recorded at the Sun King Brewery. Simpson is often to be seen playing acoustic guitar, leaving the electric shenanigans to fellow bandmates, as he gets frustrated with the search for a tone that playing electric entails. Though Tele player, Adam Davis, has clearly found his own tone on this track as demonstrated by the gloriously understated solo:

Number 9: ‘Long White Line’ from ‘Metamodern Sounds in Country Music’ (2014)
At one level a trodden path theme of the truck driver hitting the road for an unfulfillable search but also about the past being too painful a place to stay in any longer and the need to move on emotionally and physically. This track features, Laur Joamets on Telecaster showcasing his not inconsiderable talent:

Number 8: ‘Life Ain’t Fair and the World is Mean’ from ‘High Top Mountain’ (2013)
This time Sturgill is seen taking the Telecaster reigns with his Sunday Valley bandmates. Whilst musically, the track sits in a traditional country groove, beneath the surface the lyrics suggest that of course life is unfair but complaining about it, as so many country songs do, may just be a poor excuse for not pursuing your dreams and overcoming adversity:

Number 7: ‘Sometimes Wine’from ‘Cuttin’ Grass, Vol. 1: The Butcher Shoppe Sessions’(2020)
This is bluegrass inspired foot-stomping goodness. When you have rhythmic trickery, coupled with lyrics like, “I have always tried to keep my glass full / Sometimes whiskey & sometimes wine /Baby, why is it whenever your glass gets empty /You come along and knock over mine”, what’s not to like?

Number 6:All the Pretty Colors’ from ‘Cuttin’ Grass, Vol. 1: The Butcher Shoppe Sessions’ (2020)
Sierra Hull, Scott Vestal, Stuart Duncan and Tim O’Brian all join Simpson on this track lifted from ‘Cuttin’ Grass Vol 1′ to supply some good old finger pickin’.

Number 5: ‘Listening to the Rain’ unissued live cover version.
Simpson lends his unique sound to this Osborne Brothers classic.

Number 4: ‘Turtles all the Way Down’ from ‘Metamodern Sounds in Country Music’ (2014)
Wikipedia describes the song’s title as the “Expression of the infinite regress problem in cosmology posed by the ‘unmoved mover paradox” which may leave you none the wiser as to the song’s actual meaning but when Simpson sings, “Marijuana, LSD / Psilocybin and DMT / They all changed the way I see / But love’s the only thing that ever saved my life” he may be saying that it might as well be ‘Turtles all the Way Down’ until you hit love.

Number 3: ‘Just Let Go’ from ‘Metamodern Sounds in Country Music’ (2014)
Taken from, ‘Metamodern Sounds in Country Music’ , Simpson says the word ‘metamodern’ encapsulates his view of what country has to be: “You can embrace nostalgia and history and tradition, at the same time – it has to progress or it can’t survive.” The opening lines of, ‘Just Let Go’ have to be amongst the more attention-grabbing you might come across: “Woke up today and decided to kill my ego”. Present on this track is also some of the analogue studio trickery beloved of its producer, Dave Cobb.

Number 2: ‘Time After All’ from ‘High Top Mountain’ (2013)
Just Simpson and acoustic guitar managing to be philosophical whilst not letting go of that alluring rowdiness that permeates his work.

Number 1: ‘The Promise’ from ‘Metamodern Sounds in Country Music’ (2014)
The dynamics of this song are perfect. Simpson’s voice commences the song with a subdued tone with the emotion gradually rising to the surface reaching a cathartic crescendo in the finale. The arrangements are sublime with ethereal strings providing a floating backdrop to the rest of the band – bliss.

About Richard Phillips 45 Articles
From the leaden skies of Manchester to the sunny uplands of Cheshire, my quest is for authentic Americana. Love live music, my acoustic guitar and miss my baby (grand piano).

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