Getting to listen to Sturgill Simpson on repeat for the past two weeks in preparation for this blog post has been a real treat for me. Narrowing it down to his top 5 songs, however, was much more challenging.
I used three criteria when selecting these songs. To me, good music is the kind that makes you want to move your feet. So, the first thing I looked for was songs that are fast paced and make me want to drop what I am doing and dance. The second thing I looked for was songs that provided the greatest wisdom and life advice, which so many of Simpson’s songs offer. Lastly, I looked for moments that showcased Simpson’s sheer, raw talent — because there’s a lot of that to go around, too.
Granted, you can find all three of these criteria in every single one of his songs, but the following songs are the ones that stood out to me.
This song is from Simpson’s 2013 album High Top Mountain. It’s about the plight of a struggling artist who has a wife who wants to start a family. In my mind, Simpson is such a well-established artist that it’s hard to imagine him as an up-and-coming artist, so hearing about what he might have experienced is just fun.
This song makes the top five easily because of it’s memorable vulnerability. The second song on A Sailor’s Guide to Earth, it’s a soft and slow lullaby for Simpson’s son. It starts with the sounds of a bird, and shortly after Simpson’s delicate voice comes in, offering words of comfort from across the sea. The sailor tells his son that thinking about their love is the only thing keeping him sane. Simpson comforts his son in this song the same way he would if he were in his arms, but it also seems like he’s comforting himself as he feels guilty for not being there for his child.
This next one comes from Metamodern Sounds in Country Music that was released in 2014. On this track, Simpson sings about heartbreak in a “you just have to roll with it” fashion that is pretty common in his songs. The fast tempo keeps the mood light even as Simpson sings about heavy things like paranoia and drinking himself silly. It makes for an interesting dynamic that helped push this song into the third place spot among all other Simpson songs.
The second place song is also from Metamodern Sounds. This song is a walk down memory lane, as it depicts childhood memories and simpler times. It’s a song about missing people, it’s a song about gratitude, it’s a song about living in the moment and remembering your roots. As Simpson expresses gratitude to family members who touched his life, he encourages listeners to reflect on their own experiences, which is what makes the song so powerful (and a shoe-in for second place).
This song is also from A Sailor’s Guide to Earth, and it takes the cake. Not only is this song undeniably fun, but it’s also practical and sensible. I mean, come on, “Keep your head out of the clouds, and remember to be kind, and just stay in school, stay off the drugs, and keep between the lines,” is some pretty sound advice to follow, right? Not to mention the background vocals that say “Don’t sweat the small stuff.”
And, since Simpson’s got such an extensive repoiteroire, it’s no surprise that there are a few honorable mentions. Here are the one’s that juuuust missed the cut:
This song almost made the top 5 because it’s lighthearted and fun, but it’s also relevant. This upbeat country tune is from Simpon’s debut album, High Top Mountain, which was released in 2013. In the song, Simpson sings about being a lost sinner, a leaf blowing in the wind. He takes his humanity in stride by singing to a fast beat with lots of repetition. You could listen to this song one of two ways — at surface level as a toe-tapper, OR as a new, carefree way to approach life by accepting your flaws.
This song is also from Simpson’s album, A Sailor’s Guide to Earth (2016), which is a story as much as it is an album. Simpson produced the entire album himself after wrestling with conflicting emotions of wanting to live on the road while also missing home and his family. This internal conflict inspired him to write the album from the viewpoint of a sailor who isn’t sure if he’ll make it home safe. “Welcome to Earth (Pollywog)” opens the album and sets the tone, which is one of strained emotion and longing, because Simpson is singing to his son, who he had to watch grow up from afar while he was on tour.
And that’s a wrap! I’ve changed the order of this list at least ten times, and I’m sure I’ll never be able to officially decide on Simpson’s top five songs. The only solution I have is to continue to play his music on repeat and look forward to hearing him live at the festival in September!