Will Oldham has worn many hats during his career. He’s been a musician (recording under the pseudonyms Bonnie “Prince” Billy and The Palace Brothers), an actor (most recently in the indie flick Old Joy) and, for at least a few years, a pirate.

Unlike the music and acting, Oldham’s short-lived pirate period is still largely shrouded in mystery. He refuses to discuss the details with journalists and strangers. What we do know is this: At some point before recording his first records in the early nineties, he took up sailing lessons and announced 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. 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.


The only remnants of Oldham the pirate enthusiast can be found in the occasional song lyric, like this one from “Stable Will”:

If god has teeth I have none
Like a pirate prevail
Upon the silver raiding ships
Merciless men are few

Some might argue that the whole thing was a joke. Oldham never seriously contemplated a life of piracy. And if he did, it was just a momentary lapse of reason. I sat down with Oldham to find out.

Eric Spitznagel: So what we really want to know about are the pirates.

Will Oldham: (Long pause.) Okay.

How does that happen, exactly? Is it just something that a person falls into? Or do you make a conscious choice, “Y’know, I’d really like to be a pirate?”

I don’t think that word – the word “pirate” – has any real meaning. Or it’s something that’s had meaning imposed on it. The people who we’d label as pirates, who are doing things that we’d identify as pirating – taking over boats and robbing them of their cargo – down in Southeast Asia or the Spice Islands or Indonesia or the Philippines or wherever, I don’t think that word is even a part of their everyday lexicon. Do they say, “Here we are, pirates?” Or do they just say, “There’s a boat over there that has some stuff on it, we should take that?”

So a true pirate would never call himself a pirate?

Yeah, yeah. It seems that most successful piratic acts are done incognito, or under the radar. Because if you’re trackable in what you do, then you’ll be apprehended and condemned. It’s wrong to think of pirates as something organized and recognizable. It’s only after an act of piracy has been committed that you can recognize it and call it that. Pirates are talked about in history and in fantasy story books as these identifiable things, as these groups of people who act a certain way and talk a certain way and do certain things. But they’re not really anything, you know? They’re just shadows. They’re the shadow selves of these things that they leech off of.

If you think of it that way, I suppose the word “pirate” isn’t really a noun at all, but a verb. It’s not defined by who you are, but what you do.

Around the same time that I was thinking about all this, I remember getting a letter from a friend, and he had determined in this letter who he was. And I think that stalemated me for a little bit. In my thinking, you were as much what you were becoming as what you were. Or rather, I had to do something in order to be who I was.

So you thought that by taking these sailing lessons, you’d figure out whether you really wanted to be a pirate?

No, not that I’d figure it out, but that I’d become that, y’know? I believed that you had to become who you are rather than just being who you are. It was about thinking that there’s an escape, that at any moment I could see a path that looked attractive and I had the option to walk down it. It’s thinking, “Well, being a pirate looks like a cool thing to do. So if I believe in that enough and do things that I associate with being a pirate, I will become that thing.”

But isn’t that true? If it looks like a pirate and acts like a pirate, doesn’t that mean it’s a pirate?

Not really. Because it’s just an idea of who you are rather than who you are. It’s like when you’re talking to someone and they say, “I’ve always wanted to learn French.” They never wanted to learn French. They never ever for a fucking second wanted to learn French. They wanted to be somebody who spoke French, but they don’t actually want to learn that skill. They just liked the idea of being that person. By saying that I want to be a pirate, simply by the act of saying it, all of the work is done for you. A pirate is something.

I’m endlessly fascinated by how a person makes that transition from fantasy to reality. How does somebody go from reading about pirates and daydreaming about pirates to thinking, “This is something I can actually become?”

If it gets to that level, that is something I would call insanity.

You would?

I would, unequivocally, call that certifiable insanity.

Why so? What makes it insane?

What makes it not? I think everything makes it that way. I can’t think of a single thing that doesn’t make it insane.

Insane would be saying, “I want to be a fire truck.”

What’s the difference? I don’t understand the difference.

You can’t be a fire truck.

But there are a lot of great things about being a fire truck. A lot of admirable things. There’s very little admirable about being a pirate. There’s very little functional about a pirate. There’s very little real about a pirate. I would feel safer with somebody who wanted to be a fire truck than somebody who wanted to be a pirate.

I’d agree that a fire truck is a slightly less threatening fantasy than being a pirate. It doesn’t require as much plundering. But at least a pirate is possible. You can never be a fire truck. You can wish all you want, but you’re never going to grow wheels and turn your skin into metal. But you can get a boat and go out on the high seas and rob people and call yourself a pirate.

I don’t believe you.

You don’t think so?

Can you tell me somebody who did?

Well, no, not personally. But that doesn’t mean it can’t be done. I don’t know anyone who became an astronaut, but I know that being an astronaut is something achievable.

Not really, though. I think it’s pretty unachievable for most people. Just think about how many people are on the planet and how many of them have become astronauts. It’s a pretty small percentage.

But that doesn’t mean it can’t happen, does it?

I think it does. It’s like with John Walker Lynn trying to become an Al Qaeda soldier, which he did very pathetically. And that’s because it’s impossible for him. And it’s even more impossible for anybody to become what you and I are accepting as a p-i-r-a-t-e.

It just sounds to me like a form of self-sabotaging. Granted, John Walker Lynn wasn’t a very effective terrorist, but he did it. He was a terrorist, even if he ended up being a crappy one. Doing something badly is very different than saying that something can’t be done.

Maybe. But I still think it’s in the realm of fantasy. It’s like wanting to be an angel. For me, there’s very little difference between wanting to be a pirate and wanting to be an angel. And in both cases, we get a lot of our inspiration from movies. I want to be Cary Grant in The Bishop’s Wife just as much as I want to be Errol Flynn in Captain Blood.

Well, sure. But again, I can pick up a newspaper and read about pirates attacking a cruise ship off the Somalian coast. But I don’t think I’d find quite as many stories about angels.

You don’t believe in angels?

I think it’s more reasonable that somebody would say, “I’m moving to Indonesia to become a pirate” than, “I’m flying up to heaven to become an angel.”

You think so? It still seems like the same thing to me. Because both a pirate and an angel are about escape. When I was a kid, I read about pirates like John Rackham and how he traveled the world and had all these exciting adventures. And I remember thinking, did he really become these things that people liked to write about? Maybe he was just a diseased loser who wanted to escape, escape, escape, escape and then failed, even at his escape. That escape from the real world seems like the main reason why somebody would want to be a pirate, and maybe also why somebody would want to be an angel.

I suppose. But you’re going to find more young boys dreaming of being pirates than angels. Pirates are just inherently cooler, if only because of all the hyper-masculinity.

See, I don’t have an attraction to any of that. I’d think being an angel would be just as cool. (Laughs.) I would probably have the same pair of testicles in either occupation.

I don’t know, Will, I’m having a hard time buying this. Isn’t lashing out at fantasies a weird stance for somebody who ended up in the arts? Do you really want to be the guy who takes aside an artistic kid with an active imagination and tells him, “You want to be a pirate? Oh, grow up!”

Yeah, but it’s not about losing touch with your imagination. It’s not the artistic kids who have a difficult time letting go of the pirate fantasy. It’s the kids who grow up to be frat boys and executives. They become like real pirates. They still rape and pillage, they just don’t do it with the Long John Silver hats and the cardboard swords. They’re the natural descendants of Tony Scott.

Yeah, I suppose that’s true. But still, there’s that little boy somewhere in my head that still wants to believe that anybody can be a pirate if they want to be.

And that’s cool. It’s not about giving anything up. It’s about the constant recycling and upgrading of your dreams as you get older. When you realize that you can’t be a pirate, does that mean you have to throw away all of that imagination, all of that aspiration, all of that optimism, all of that excitement? No. It doesn’t. But you can’t be a pirate! No! It doesn’t matter how much you want it, it’s still a lie. It’s trying to define yourself by becoming something else, something that doesn’t exist. I have more respect for somebody who points at his ideal – in this case, the ideal of the pirate – and then becomes something that’s more radical, more exciting, more subversive than a pirate could ever be. You have to trade in your fantasy for something better, one that incorporates everything that you loved about the dream pirate but is more uniquely you.

So it’s not about clinging to the details of being a pirate, like stealing treasure chests and making people walk the plank…

Unless that’s what you’re into. If you’re into the raping and pillaging aspect of being a pirate, then you should trade up on that and become an executive. And that’s where you can rape and pillage. You shouldn’t just be a disgruntled pirate at age 45, thinking, “God I wish I’d raped and pillaged more.” Those aren’t the people who are fun to hang around with.

Okay, okay, I think I see where you’re going with this. The inner pirate doesn’t go away, it just changes and evolves into something that’s actually attainable?

Yeah, yeah. Approaching your dreams that way is so much more satisfying than what you could get by trying to be a real pirate. Some people are able to transfer what they were idealizing about raping and pillaging and decapitating and marooning and turn it into something positive. Like… I don’t know… how to train your dog.

You lost me again.

Or maybe it’s the fierceness and cruelty of being a pirate that appealed to you. They can satisfy that need for fierceness by instilling it in their art. Maybe they’ll make art that, in some way, tortures people, either by listening to it or looking at it or consuming it. And by doing that, you’ll give the pirate another five years of safe existence.

Wow. I guess that means GG Allin was a frustrated pirate, right?

Yeah, sure. And if you think about it, all porn stars are pirates.

O-okay. But how so? I get the whole phallic “sword” comparisons, but how else are they like pirates?

I think that porn stars and pirates are like constellations. Everyone can see it, everyone can recognize it, and it’s very difficult to criticize because it’s not right in your face. Ron Jeremy is not doing me direct harm. But do I think maybe he’s more harmful than another citizen of the planet? He might be.

I don’t think that anyone would argue that Ron Jeremy is a pirate. But as for the rest of the porn industry, I just don’t know.

The thing about being a pirate is that anybody can do it. You can put on an eyepatch and a bandana and a gold earring, but that doesn’t really make you a pirate. It’s the behavior not the costume. To be a porn star, all you have to do is take your clothes off. That’s it. You put a video camera in your bedroom and you’re a porn star. The dream of being a pirate is tied to the ocean, so the whole Midwest is fucked. They can’t be pirates. But even if you live on a coast, what do you do? Spend $70,000 to buy a yacht? Cause those are the only things that resemble what we think of as a pirate ship. But everything that resembles being a porn star, you can do that pretty quickly.

Okay, I’m starting to come around. And then there’s the whole outsider aspect. A pirate is somebody who breaks off from society, becomes a rogue, and does things that might be considered amoral. You could use that same definition to talk about porn stars.

Yeah. Pirates and porn stars both travel in groups, and ironically they both die unhappy and alone. Pirates say “Arrrrr” and a porn stars says “Ooooooh!” Instead of a rousing sea shanty, it’s (imitates a funky porn soundtrack) “Bw-waah-wah,wuh-wah!” They share a lot of the same cultural archetypes, just slightly shifted.

What about musicians? Do they qualify as pirates?

Well, sometimes, There’s the junkie artist-musician who in some ways functions as a pirate, because they lie and steal, and people admire them.

It’s not a coincidence that Johnny Depp based his character in Pirates Of the Caribbean on Keith Richards, who might be perceived as the ultimate modern pirate.

Yeah, but see, I disagree. John Bonham was closer, probably. But these big rock star guys have agents and managers, they’re signing contracts, they are not pirates. They’re nothing like it. They’re completely within society. They’re slaves of Babylon and politics. They are not pirates.

Okay, you’re right, I stand corrected. Keith Richards is probably not going to die unhappy and alone.

He is going to be happy until the last fraction of eternally subdividing seconds of his life.

What about musicians who work outside the mainstream, making and selling their music on their own terms? Do artists like Ani DiFranco and John Darnielle seem like pirates to you?

No, not really. The thing about pirates is that they take advantage of other people’s labor. So the do-it-yourself musician would be like the guy who owns a merchant ship and refuses to align himself with a union of sea-going vessels. He’ll say, “I’m going to do business with these ports and not these other ports, and I’m going to trade these items and not these items.” Whereas, a pirate would just wait for that person to get far enough away from shore and then he’d attack and steal everything. I think that America in general is piratical. Every time we accept a paycheck for doing almost nothing, allowing us to live above the poverty line, we’re engaging in piracy.

So it doesn’t matter if you’re actively harming someone? Just being on board the pirate ship makes you a pirate?

I think so. I think a witness does as much harm as a perpetrator.

Well, if your metaphor is correct, and simply living in this country makes us pirates, I guess this means you ended up being a pirate after all.

(Long pause.) I guess it does.