Singer-guitarist Sturgill Simpson performs at PNC Music Pavilion on May 26, 2018 in Charlotte, North Carolina.
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6 Sturgill Simpson Songs That Prove the Country Trailblazer Plays By His Own Rules

Sturgill Simpson has forged his own path in country music by famously playing by his own rules and making the kind of music that is true to him. As an independent artist for much of his career, Simpson has had the freedom to create his own route, and he has built a dedicated fanbase as a result. He does his own thing, but he hasn't always done so quietly. Some may remember the demonstration he staged outside the CMA Awards in 2017, standing outside the arena the night of the awards show and asking for tips while playing guitar. Although Simpson's tactics are sometimes unconventional, his talent is undeniable, and his discography of nearly 10 years shows this clearly. Although Simpson proclaimed that his 2021 album would be his last, let's hope his music-making days are far from over. For now, here are 6 of his best songs so far.

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6. "I Don't Mind"

Simpson employs the Bluegrass sounds of his Kentucky roots in his song "I Don't Mind" from his Cuttin' Grass - Vol. 1 (Butcher Shoppe Sessions) album. In this tune, he sings from the perspective of a heartbroken man who left a relationship and now deeply regrets it. Simpson poetically describes the way he feels in the tune, and a few standout lines include: "There's a lonely feeling I carry / That will follow me all my days" and "But you drift in and out of my dreams now like a ship out at sea in a storm." There's not much redemption for the main character of the song. He simply stays heartbroken while welcoming his love's potential return. "If you think you can ever love me again / Please go ahead, I don't mind," he sings.

5. "Call To Arms"

While other songs by Simpson may explore the subjects of life or love, his tune "Call To Arms" from his album, A Sailor's Guide to Earth, is much more than that. This song falls close to the protest song category as Simpson comments on various hot-button issues such as war, social media addiction, dishonest government and the opinions of the Hollywood elite. The song focuses mostly on the effects of war on young soldiers, but all these issues are intertwined.

4. "Juanita"

Simpson's song "Juanita" comes from his album, The Ballad of Dood and Juanita, released in August 2021. The album was written and recorded in a week with a group of musicians called the "Hillbilly Avengers," and it's a concept album. This song employs a Tex-Mex musical style as Simpson sings of a long-lost love named Juanita. Other songs on the album, such as "Ol' Dood" (Part 1 & 2) and "Sam," continue to tell this story. 

3. "You Can Have The Crown"

"You Can Have The Crown" from Simpson's debut album High Top Mountain clearly showcases his traditional country sound and his clever songwriting. In this tune, Simpson sings from the perspective of a man who is simply down and out. He's addicted to "weed and pills," he has no money, his wife wants a baby and nothing seems to be going right. The downtrodden nature of the man is apparent in the chorus as Simpson sings the hook: "Well they call me King Turd up here on S— Mountain, if you want it you can have the crown." Although the song is sad, one can't help but chuckle at Simpson's humorous, self-deprecating songwriting, which is reminiscent of legendary artists like Johnny Cash and Waylon Jennings.  

2. "Turtles All The Way Down"

Simpson takes listeners on a wild trip in his song "Turtles All The Way Down" from his Metamodern Sounds in Country Music album. The song begins with the sounds of 1970s outlaw country as Simpson sings about seeing Jesus, the devil and Buddha in various situations. He continues, singing about a "gateway in our minds" that leads to a place where "reptile aliens" "cut you open and pull out all your pain." These far-fetched ideas do have a point, though, as it becomes clear he is singing about the effects of psychedelic drugs. Simpson shares support for these drugs in the tune, but it's not so much a protest song about the legalization of drugs as it is a sonic journey Simpson offers to the listener.

1. "Long White Line"

Simpson fully taps into 1970s outlaw country influences in his song "Long White Line" from his Metamodern Sounds in Country Music album. Mirroring those classic songs of the past, this ramblin' tune finds Simpson singing about hitting the road and driving until it runs out — literally. In the song, he sings of his desire to keep driving until he finds the end of that "Long White Line." The song not only recalls country music of the past with its classic sound, but the song's premise of getting lost on the open road is reminiscent of music from artists like Waylon Jennings, Merle Haggard, Willie Nelson and many others.

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