Sturgill Simpson: Man Of The Hour

This article appears in our upcoming May/June “country” issue. Subscribe here. On a cold and clear day in January, Sturgill Simpson has just made camp in Chicago. He and his band drove in from Clear Lake, Iowa, where they opened for Dwight Yoakam at the Surf Ballroom the night before. Surf is famous for being the last venue Buddy Holly, The Big Bopper, and Ritchie Valens played on February 3, 1959, the night they boarded a plane that would only make it about six miles outside of Clear Lake before crashing down in stormy weather. “They still have the phone booth that they all called their wives from that night,” says Simpson. The young bass player in Holly’s group, Waylon Jennings, didn’t get on the plane that night. He gave up his seat in a coin toss and went on to become one of the founders of outlaw country, a sub-genre that still has a strong foothold today with artists like Jamey Johnson and Eric Church. “The most outlaw thing that I ever done is give a good woman a ring,” sings Simpson on “Life Ain’t Fair And The World Is Mean,” off his new album, High Top Mountain, which…

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