By Arielle Castillo | May 26th, 2011 | 1 Comment

Reports of Will Oldham’s supposed elusiveness have been greatly exaggerated. Several notable past press accounts have found Oldham, who performs most often as Bonnie “Prince” Billy, reticent in discussing himself or his works. In 2009, his own mother described him as “ornery” to the New Yorker’s Kelefa Sanneh, in a story whose narrative hinged largely on a city mouse following Oldham to a secret concert given in the rural outskirts of his native Louisville.

Maybe this is a result of confusing the music with the man. Oldham’s overwhelming body of work, starting with the material he released as Palace Music (or Palace Brothers, or Palace Songs) in the early ’90s, can seem hard to penetrate.

There’s no clear starting point for the new initiate, although any is equally good. While certain discs, like 1999’s I See A Darkness, have by now been critically canonized, they’re not dramatically better or worse, or more or less accessible, than the rest.

Oldham’s material is, in most simple terms, folk, but often with a marked Southern gothic bent, and the easy acceptance of mortality that runs through so much of the music of Tennessee and Kentucky. Songs amble, bend, and wander around, sometimes at a dirge-like pace. They obliquely recount tales of drinking, love (usually lost), and other misfortunes, in a way that allows you to be sure Oldham is speaking directly to your pain and nobody else’s.

But the thing is, it’s not all gloom and doom if you pay attention. At the end of all that twangy rambling, there’s usually a light at the end of the tunnel, whether in words or pure sound. Even the title track of I See a Darkness — a song that mournfully repeats the refrain of the title — turns brighter in the end. Oldham turns hopeful as he sings, just as some major-key piano chords take the song out to a question-mark end.

And when I spoke with Oldham recently by phone, he was downright cheerful. Maybe it’s because he really, really likes Florida, or at least the idea of it. This month kicks off his Free Florida tour with pal Emmett Kelly (a.k.a. the Cairo Gang), which finds the duo performing a series of free record-store performances throughout the state. Two of those are here in South Florida: Monday, May 30, at Radio-Active Records in Fort Lauderdale, and Tuesday, May 31, at Sweat Records.

But with Oldham launching one of these free tours, by his own account, about once every dozen years, why Florida, of all places? I reached him by phone at his Kentucky home to find out. Birds chirped loudly in the background as we spoke.

What is your personal experience of Florida? How much time have you actually spent here?

Will Oldham: I’m 41, and I probably started going there when I was seven or eight with the family. Then when I got older, I’d go there to play music, and I know we went to Cuba a couple times and had to do that with Miami as a starting point. So that’s been it — spending time there on intense family vacations, and playing music.

You’ve actually been to Cuba? When was that and how did you manage it?

WO: The first time we went, we kind of snuck over and we got nailed on the way back, which kind of sucked. Both trips were in the late ’90s, probably like ’96 and ’98. The second time, my friend Bob Arellano, who’s a musician, assembled this quasi-supergroup, and got us a gig at a music festival in Havana. We got special licenses from the U.S. government to go to Cuba for 10 days or so and played three shows. So the last time was totally legal and totally awesome.

You’re known for having wide, deep, and obscure musical tastes. Were you into any Cuban music before you went there, or did the trip spark any further interest in it?

WO: I don’t have a deep knowledge of Cuban music, although I definitely had a rudimentary knowledge, and more from records Bob had played for me. The first time we went there I did a fair amount of record shopping, which was very exciting, and not very expensive. Unfortunately, since we didn’t go legally that time, on the way back in all those records were confiscated by U.S. Customs. They were actually broken in half.

So besides those trips, have you been to Miami?

WO: Yeah, besides flying out of there to go to the Bahamas and Cuba, there was a time about eight years ago when I wanted to learn some basics of recording. There were different places in the country where I could do it, and one was in Miami. So I went there and studied recording for just a couple of weeks. I can’t remember what the place was called, but it was at a place that was endorsed by ProTools to teach ProTools.

So what’s behind the timing? Why this Florida tour right now?

WO: I found that it makes more musical and personal sense to do tours in a way that has meaning just beyond the material. I like doing geographically specific tours, because we can learn about where we are, and be influenced by where we are, as opposed to hitting Tallahassee and Orlando, and then going to Savannah and Charleston. It doesn’t allow you to appreciate anything about the places where you’re going.

When we’re in Florida, we’ll be able to spend two nights in the same bed, for example, and we’ll be in the same state day after day. It’ll also be fairly interactive because we’ll be in these record stores, and we’ll talk to people afterwards, and we can learn things about people’s lives in the state and how we can interact with the state.

It’ll be three of us, me, Emmett Kelly, and Angel Olson. And Emmett has never been to the state of Florida. We’re working on a record, but there was this gaping moment of time — I hadn’t played a show yet in 2011. So we thought, what could we do in the spring that would be exciting for us? So we thought we’d see if we could get to Florida, and have it be logistically minimal, so our connection to the places where we are, are maxed out.

We won’t have a tour manager, for instance, and we’re not getting paid, so we won’t have to spend two hours at the end of the night figuring out how to get paid. We’ll just come in, play music, and then leave when we’re told to leave.

Are you worried about finding a way to monetize the tour at all, or are you just subsidizing it with other projects?

WO: Subsidizing it from other stuff. With three of us traveling with no crew or anything, we’re not staying any place fancy. It’s not a hugely expensive trip, and part of it is using income that’s been made from selling records to people. In some ways, we got paid and now we’re doing the work.

That’s interesting, because most people are doing the opposite, where they have to subsidize their recording by playing.

WO: Honestly, that is more and more how it’s going. But even so, playing guarantees our kind of going up … For instance, if I play a festival, I don’t really like to play a festival, but that money can pay for a free trip through Florida. And I don’t know what else to spend it on, you know? Might as well use the money to make music.

What appeals to you about doing this trip through Florida, specifically, as opposed to another state you might not get through too often? You told Miami New Times, for instance, “There’s more to discover in Florida than Cincinnati or Columbus.”

WO: Well, that’s because I grew up near Cincinnati, so certain things are just inherently part of my upbringing, and it’s a great opportunity to go someplace else. That’s one of the advantages of doing this work, of playing music. It can be the magic carpet that gives you access to another place.

Florida’s populations are pretty diverse. I would say overall, the depth of the cultures of radically different groups is very different from that of Kentucky or Ohio. We’ve also had a brutal, brutal winter here, so as I’m getting older, I might as well start experimenting with the idea of traveling to Florida to lick my wounds.

One song I’ve always wondered about is “West Palm Beach”. Did you really have a grandmother there? Why write a song about West Palm Beach, specifically?

WO: My father’s side of the family spends time near there, in Delray. It’s been a place that we’ve visited for many years. Each time, when a northerner — northerner, in relationship to Florida — goes to Florida for those reasons, especially if it’s an annual thing that begins at a young age, each trip you’re the same person, but also a vastly different person.

Your relationship to the place goes through these changes with you, and that was the idea of trying to put into a song the intensity of the sporadic relationships. And the sporadic relationships as well with that community of people — the other people who have sporadic relationships with the place, and also the people who have a permanent relationship with the place.

That’s different from when I look around here on my block in Kentucky, where people are used to things staying the same. It’s a different mindset when the population is shifting constantly in both big and little ways, and I think it’s something a Floridian goes through much more often than a Kentuckian.

Why did you choose West Palm Beach rather than, say, Delray?

WO: Partially that’s because West Palm Beach is a little bit bigger. Anyways, I find that the reason of making music and making songs is not to broadcast the specifically personal, but to find some kind of common ground, to either build it or find what already exists. So rather than say, “This is my specific experience,” it’s more like opening it up to people who might have a shared experience.

What are you most looking forward to exploring between shows? Do you have any kind of plan or agenda?

WO: I don’t know if there’s any reason to anticipate, on the Eastern coast, any kind of wave activity, but I would definitely be excited if there was anywhere along the way. After we hit Pensacola, we will drive across the panhandle, and we intend to swim right away in the Waukula Springs.

A lot of that will be showing Emmett, since he’s never been to Florida before, things I like. And a lot of it will be really basic stuff, like the kinds of people that live there, the kinds of houses that are there, what the roads are like, what the flora and fauna are like. We’ll keep our eyes out for wild animals that we don’t have up here. And grouper sandwiches!

And in Miami we’ll be playing at Sweat Records, which is in Little Haiti, so that’s exciting. I’ve only been to Little Haiti once before, and that was to look for Haitian record shops. So hopefully there will still be some of those.

Then I’ve got family and friends along the way — I’ve got family in Fort Lauderdale now — so we’ll be beholden to tour guides along the way.

Is this a touring model that you will repeat in other states, or did you save this for Florida since it’s relatively remote on the touring circuit?

WO: The first one I ever did that was like this was the West Coast — California, Oregon, and Washington. That was probably ’99, I think. Then the second one was in Scandinavia, when I went by myself and played in record stores and radio stations in Norway, Sweden, and Denmark (no shows in Finland at that time). I liked the way those trips felt so much, I felt like I could venture into an otherwise, for me, very emotionally challenging place for me to travel, which was the Midwest. So I did a trip around the Midwest, again by myself.

This will be the first time I do it in company, with this trio. Touring and playing shows oftentimes ends up being a destination unto itself, and being someplace nice is gravy. But when there’s a place worth exploring, it’s nice to be able to do this kind of thing. It’ll be a very interactive trip for us, and it’s a place that, from my experience in the past, merits that kind of time and interaction.

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