Sturgill Simpson, known for his unique approach to country music, shook up the Tiny Desk concert with his raw, unfiltered performance. The 36-year-old Kentucky native, sporting a casual ensemble, delivered songs that delved into themes of drugs and drinking. Starting with "Turtles All The Way Down," Simpson's set included introspective tracks like "Time After All" and "Life Of Sin," culminating with the melancholic "Water In The Well." Simpson's style, often likened to outlaw country, has garnered critical acclaim and accolades. With seven solo albums to his name, including Grammy-nominated releases like "Metamodern Sounds in Country Music" and "A Sailor's Guide to Earth," Simpson continues to push boundaries in the genre. His most recent album, "The Ballad of Dood and Juanita," released in 2021, may mark the end of his chapter as Sturgill Simpson, leaving fans anticipating what's next from the unconventional country artist.