WAIM #109: Will Oldham

If you have paid much attention to the worlds of indie rock, freak folk, and independent film in the last four decades, it’s likely that you have encountered some of the work of singer, songwriter, and actor Will Oldham. Oldham was born into a Louisville, KY family that was home to a robust record collection, and a deep regard for art and music.As a teenager, Oldham began acting in the Lousiville theater scene and quickly landed a role as a feisty young preacher in the John Sayles film, Matewan. The experience helped him to understand the ingredients for healthy artistic collaboration. The experience also set the bar pretty high in Oldham’s mind as to what could be achieved when a group of artists and craftspeople all pull in unison in one artistic direction.By the time he had finished high school, his parents had gifted him a guitar and he’d begun to learn to play familiar songs and quickly began writing his own. With his brothers, he formed a nascent band they dubbed Palace Flophouse. Will, and his brothers with varying degrees of input would make records under a variety of monikers like Palace Music, Palace Bros., or even simply Palace throughout much of the 1990s.By the late 90’s, Oldham had settled upon the moniker of Bonnie ‘Prince’ Billy, releasing a string of critically acclaimed records that featured songs that were eventually covered by a series of massive artists including Johnny Cash, who recorded a version of the Bonnie ‘Prince’ Billy tune, ‘I See A Darkness’.In addition to an extensive catalog of releases centered around his own songs, Oldham is a supreme interpreter of other songwriters as well. He’s made a series of recordings that feature terrific cover versions, including a pair of records done in tribute to the Everly Brothers and Merle Haggard respectively.Bonnie ‘Prince’ Billy continues to record and tour with regularity. As Will and I discussed in our chat, he had just been booking hotel rooms for a show in Indiana the afternoon that we sat down together. And while he has learned to truly harness the joy of live performance, something that came to him later in his career, Will has grave concerns about the state of the music business, and the way fans are currently investing in and engaging with the music they enjoy.This is a roving and riveting discussion with a truly visionary, and one of a kind artist. Will shares how human relationships have always been at the core of his work, and talks about the ways that he and his band use as much local crew as possible at their tour stops to connect with local music communities in a more foundational way. We explore the artistic endeavor of being an audience member, and we take a look at how letting your guard down leads to the most magical moments of all.Cheers,Matty C Get full access to What Am I Making at whatamimaking.substack.com/subscribe