Crying in Music: Darrell Scott’s Honest Artistry

The cover of Darrell Scott’s latest album, Old Cane Back Rocker, immediately sets the tone for your listening experience. The inclusion of the names of the Darrell Scott String Band (Bryn Davies, Matt Flinner and Shad Cobb) lets you know right off the bat that this recording is a band effort. The photo on the album cover gives a visual of Scotts’ family roots in rural Kentucky. His cousin Dwight Messer is standing in front of his former childhood home, now abandoned on the family land. The music reflects his family’s story: some, like Dwight, stayed behind and some, like Darrell’s father, Wayne Scott, moved up north to find work. Despite being raised in the north, Darrell’s home has always felt like Kentucky and traditional music learned from there. These songs showcase those roots.

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In our conversation, Darrell digs into the darkness that can be heard in his music, even if it’s not a sad song. He talks about his friend and frequent collaborator, Tim O’Brien, and how his performance and writing has allowed Scott to level up. Darrell also speaks to leaning into emotional songwriting and trusting his tears during the creative process. He shares the emotional account of rerecording his father’s song This Weary Way and how he used to think Hank Williams had actually written it. Immediately after we finished our interview, lizzie texted me “what a cool eccentric intellectual dude.” Couldn’t have said it better myself. This episode honestly discovers the true essence of Darrell Scott—an artist whose music resonates with the soul, rooted in the traditions of Kentucky.