Will Oldham, Who May Have Briefly Been a Pirate, Thinks Keith Richards Is Not a Pirate

On the 25th anniversary of his seminal album "I See a Darkness," Will Oldham explains why wanting to be a pirate is like trying to be a fire truck.

Will Oldham has worn many hats during his career. He’s been a musician, recording over two dozen albums as Bonnie “Prince” Billy. His debut, I See a Darkness, is celebrating its 25th anniversary this week. He’s been an actor, with memorable turns in movies like Old Joy and Jackass 3D (when he played a gorilla trainer). And for at least a few years, Oldham was a pirate.

Unlike the music and acting, Oldham’s short-lived pirate period is still largely shrouded in mystery. He’s declined to discuss the details with journalists. What we do know is this: At some point in the early ‘90s, he took up sailing lessons and announced to friends his intention to become a pirate. Where any of this happened and for how long, he won’t say. Just how close he came to becoming a bona fide pirate, he refuses to elaborate. In interviews, he’s alluded to a “catatonic episode” that occurred around the same time that his pirating ambitions died, but the specifics are not something he’s willing (or ready) to share.

Some would argue that the whole thing was just a joke, that Oldham never seriously contemplated a life of piracy, and if he did, it was just a momentary lapse of reason. But maybe not. Because I am a serious journalist, I called Oldham and attempted to lure him into a discussion of his erstwhile pirating ambitions.