In April of 2014, I met a little-known 35-year-old country singer in a hotel room in downtown Madison, Wisconsin. We had arranged an interview after I became obsessed with his latest album, a rootsy psychedelic song cycle called Metamodern Sounds in Country Music, which was due to be released the following month. His publicist said I could I meet up with him before he was scheduled to play for about 50 people at a bar down the street.
Fortunately, he was feeling unusually talkative, and the interview lasted for about an hour. It’s still one of my favorite conversations I’ve ever had with a musician. We discussed his background, which was almost too good to be true for a country singer: His early twenties were misspent in his native state of Kentucky, he told me, playing in local bands and working “odd jobs — really disconnected, disenchanted, a lot of substance abuse.” He moved to Nashville in 2005 to launch a music career, but gave up nine months later “because pop-country was just at its peak saturation” and he couldn’t find anyone to play with.
After that, he and his girlfriend packed up and left the south, relocating to Salt Lake City. He went to work for the Union Pacific Railroad, trading a life of singing about trains for a career as a conductor and engineer. For a while, he loved it. Then he “screwed around and took a management position,” he said, which made him responsible for the trains running on time. If the trains were two minutes late, “a bunch of white-collar a**holes that I’ll never meet” from the railroad would call up and scream at him. Life on the rails soon soured.
As a stress reliever, he started gigging around Salt Lake City — actually, his girlfriend would book the shows without telling him. She would lure him out for a date night, and “when we get there, my guitar’s in the trunk, and I’m playing a show,” he recalled. By now he was in his early thirties, and his partner was encouraging him to take one last stab at living his dream. So, in 2010, Sturgill Simpson and his girlfriend (now wife) Sarah gave it another go on Music Row.