Will Oldham’s career has never strayed far from American folk mythology. Long before he was known as the offbeat troubadour of Palace Brothers, Palace Songs, Palace Music, and Bonnie “Prince” Billy fame, a seventeen-year-old Oldham was cast as a teenage preacher in Matewan, alongside Smithsonian Folkways artists Hazel Dickens and Phil Wiggins. As the curator of our December People’s Picks playlist, Oldham takes us on a ramble through his native Kentucky, introducing us to the folk legends he’s encountered in his work and travels, and letting us in on the songs that rattle around his head along the way. Listen to the playlist and read Oldham’s song annotations here.