Sturgill Simpson: 3 Outsiders Wax Poetic About Their Favorite Songs to Celebrate Sturgill’s 43rd Birthday

by Jim Casey

Sturgill Simpson is a musical juggernaut. Voice. Pen. Musician. He checks all of the boxes. Country. Americana. Bluegrass. He can do it all—and then some.

Compare him to whatever Outlaw-era artist ya like, but make no mistake, the Kentucky native is as original as a bottle of 15-year Pappy Van Winkle. And just as tasty. Ok, we can’t afford the 15-year, but we can dream. And Sturgill helps us dream.

In honor of Sturgill’s 43rd birthday on June 8, 2021, we tasked Outsider‘s Marty Smith, Wes Blankenship, and Jim Casey to wax poetic about their favorite songs from the Kentucky native’s catalog.

‘Living the Dream’

Marty Smith, Outsider contributor

I’m a Sturgill fanatic. I love his writing, and I love his delivery, and I love his imagery. It’s lonely, man. There’s a lot of sadness in it. I like sad songs. Maybe it’s the Appalachia in me.

Sturgill grew up in the same region I did. I’m not saying we’re similar people, because I’ve never met the man. I don’t know if we have a damn thing in common. But I do know growing up in Appalachia never leaves you. It’s in him, like it’s in me. It’s a fighter’s region. Hard workers. Not a lot of dreamers.

“Living The Dream” is centerpiece brilliance on a timeless record. Sturgill has this amazing way to lyrically circumnavigate shitty coffee, mortality, and Jesus’ sense of humor. Metamodern Sounds In Country Music is a masterpiece, the rare intersection where production simplicity intersects with lyrical complexity. How damn great are lines that put you in the kitchen in the morning, jonesing for that first sip of coffee, only to learn you don’t have any damn cream in the fridge. It’s one of those deflating moments that we’ve all lived, to which we can almost universally relate. Brilliant. Or needing means to ends that never meet? Brilliant. Or the constant noise that tells us we have to do this or that to be somebody or something or, hell, even human. But as Sturgill says, the fact is you truly don’t have to do a damn thing but die (and pay taxes—we gotta do that, too).

That record is so damn good, Sturgill suddenly had to figure out how to be famous.

‘Welcome to Earth (Pollywog)’ [Bluegrass Version]

Wes Blankenship, Outsider content producer

I specifically picked the Cuttin’ Grass: Vol. 2 version of “Welcome to Earth (Pollywog)” for, well, the pickin’.

Sturgill’s tour with Tyler Childers was the last live music event I attended before the pandemic hit full force in 2020. My wife and I had just welcomed our firstborn, a baby girl, into the world a few weeks earlier. I went with a buddy, who had just lost his dad a little more than a year before. None of the four eyes between us were dry by the time “Welcome to Earth” concluded.

The world changed forever a week later.

Thankfully, Sturgill decided to cut up his hits with some bluegrass during the pandemic (the two-minute mark on “Welcome to Earth” is when the real party starts).

Even though the lyrics mention a boy, I always think about my girl and that concert when I hear this song. And I can’t help but smile like an idiot during that all-out pickin’ solo at the end.

‘Railroad of Sin’

Jim Casey, Outsider senior editor

Back in October 2014, Sturgill Simpson opened for Jason Isbell at Nashville’s Ryman Auditorium. Yeah, Sturgill and Isbell at the Mother Church was a helluva way to spend a Sunday night.

At the time, I was a fan of Sturgill’s 2014 album, Metamodern Sounds in Country Music. His voice. The lyrics. Dave Cobb’s production. It was a winner. However, I didn’t start drinking the Sturgill Kool-Aid until seeing him perform live.

About halfway through his six-song set at the Ryman, Sturgill unloaded a blistering rendition of “Railroad of Sin” from his 2013 debut album, High Top Mountain. I mean blistering. I was floored by his musicianship. A cartoon-like light bulb illuminated above my head. Sturgill Simpson? I was now illuminated. A couple of songs later, Sturgill got a standing ovation.

I never sat back down. Just walked into the lobby to get another beer and a vinyl copy of High Top Mountain. I spin it at least once a week.