By any definition, Will Oldham is an anomaly. Though his rickety blend of country and folk has been equated to rising and falling fauna like alt-country and freak folk, his seemingly anachronistic output has never been easily defined by style or signifiers. Instead, taking cues from the traditional music of his Appalachian heritage (Oldham grew up and lives in Louisville, Kentucky) and meshing it with varied strains of old, weird Americana and his own idiosyncratic point of view, he has crafted his own genre, which he has seemingly either expanded upon or edited with each record in his increasingly vast catalog.

After stints as both an actor and an Ivy League college student, Oldham began his musical career as leader of the Palace Brothers in 1992, a loose knit bunch that morphed into Palace Music and then just plain Palace before being put to bed. After using his own name for Joya in 1997, Oldham adapted the moniker Bonnie “Prince” Billy. While the etheric dampener that marked his early recordings has been progressively lifted, whether playing with Nashville pros (as on Bonnie “Prince” Billy Sings Greatest Palace Music) or old pal Matt Sweeney (Chavez, Zwan, etc.), his eccentricity has remained apparent.

While in the past, each new record meant a new team of collaborators, the Cairo Gang’s Emmett Kelly has been a constant partnership in recent years. This affiliation has produced Wolfroy Goes to Town, Bonnie’s new album, due out next week, on which they were joined by singer Angel Olsen, piano player Ben Boye, drummer Van Campbell (also of the Black Diamond Heavies), and bassist Danny Kiely. The album is one of his most immediately arresting, with little obfuscation between the listener and the songs. Oldham and his gang are taking the album on the road, beginning with a show in Nelsonville, Ohio (a small town 60 miles southeast of Agit hometown Columbus) tomorrow night (September 27). I caught up with him first, though, on the phone from Louisville.

It seems like every interview with you starts off with the writer saying how you don’t like to do interviews. But you recently found yourself on the other side of the table talking to R. Kelly, and I was wondering if that experience changed your view of doing press.

Bonnie “Prince” Billy: No, it didn’t. But I’ve always found a value in doing press in advance of playing a show somewhere because we put a lot of time and effort into getting someplace and it feels like part of that time and effort should be doing what we can to let people know we are going to be there as we won’t be there again in the near future and it’s a one-time opportunity to connect with folks. And then I also get to talk to you and speak with somebody in advance of being there and have that fleeting connection with what’s going on there.

I’ve done just a few interviews in my life, where I’ve interviewed somebody, and they’ve all been people who are in the same line of work as I am. They’re people who I’ve spent a good deal of time listening to, thinking about and formulating questions in my head and wishing I could sit down and speak to that person. And then I got the opportunity. Because I’ve done four or five in the course of 20 years, I know that that is a rare opportunity. So I feel like, in general, doing interviews, it’s not always going to be the case where somebody is the kind of fan that I am of R. Kelly or Merle Haggard or Dwight Yoakam. Sometimes it could be close, but even then, it’s apples to oranges because it’s somebody whose skill has to do with writing about things instead of having to deal with making up songs.

Throughout your career you’ve chosen to work with a lot of collaborators. Is that indicative of not liking to confine yourself to a band or do you need to constantly have different input?

BPB: It’s taking advantage of the opportunity to continually learn more and experience more. Last weekend, I went to Renfro Valley, Kentucky, which is a historic music town and which has a venue that is frequented by big names of classic country music. Glen Campbell played there as part of his goodbye tour that he is on right now, because he has Alzheimer’s. It was a really interesting show. It was a great in some ways, but not in most ways because of the progression of his disease. At the same time, it was one of the most powerful shows I’ve ever been to and insanely moving and devastating. I was talking with my friend that I went with about how in the future, what will be an approximation of this event? Who is somebody people might go see in 20 or 30 years? My friend said how she had been on tour with a band who had opened for Duran Duran and how people have this intense connection with the music of Duran Duran. They’re still playing and they might be playing in 20 years.

For a variety of reasons—not to speak ill of Duran Duran, God bless them—it didn’t compare. Glen Campbell was a sometime-recording, sometime-touring member of the Beach Boys, and he was one of the more active session guitar players in Los Angeles in the mid-60s, playing with a huge variety of people. Since then he’s worked with so many different songwriters and singers. I remember seeing him on FarmAid when I was a kid, after the first Highwaymen record came out. I think Kristofferson had to leave early and wasn’t able to be part of the Highwaymen set so they had Glen Campbell join them. So seeing Glen Campbell, he is an extension of this storied, varied and and important American musical community. Is that going to go on? That might not be something most people care about. Someone might say Duran Duran is the same thing as going to see Glen Campbell. I’m not going to deny it—it might be true—but to me, one of the greatest values of making music is the opportunity it provides for collaboration with other people and the recognition or expansion of what is in effect a musical family. That is why... I make music because I need to make a living and we all need to make a living somehow, but the principal reason is to identify, reveal, create and establish this community thing through collaboration.

Has there been any collaboration that has dramatically made you rethink the way you play or sing or write songs?

BPB: Most have—that’s one of the values of collaboration—but I can easily say the work I’ve done with Emmett Kelly for the last six years. In some ways, it’s difficult to get specific because our collaboration has been so extensive and so varied. We’ve written songs together and performed them in so many ways and recorded in so many ways and talked about so many things and shared so many music-related ideas and dreams. But I know that the thing that keeps us coming back is that it dramatically changes who we were before the relationship.

Then there are singular moments that aren’t going to be a surprise, like being allowed into the recording studio at Rick Rubin’s house when Johnny Cash is recording a song that I wrote. I was aware that he had some physical challenges, but absolutely none of them were made apparent except for in the length of his work day, which was only five or six hours. But during those five or six hours, I was in awe at the attention to the music and the work at hand. In many cases, the big figures and the heroes are less than what they seem or what we would like them to be. But in this case, musically, this was somebody who was more than I would have expected or I would have had them be. So it is something to continue to aspire to, relating to one’s work in that way.

Getting back to the new record, was this made with everybody in one room or done in bits and pieces?

BPB: It was done in a fairly concentrated period of time, not more than a few weeks. For the first time ever in my work, we learned, practiced and performed all these songs together. But then we went into record and took them apart. We’d do a couple elements at a time, and there were times when all six of us plus Shahzad (Ismaily), who was recording the record, were there. Then there were times when it was just Emmett, Shahzad and I, and other times, it was everything in between. The idea was for the songs to have an existence and an identity prior to recording, then, to take advantage of the recording process, to create something hyper-real, rather than just capture the songs, because we’re going to be doing that live. We wanted to create something that couldn’t be reproduced live, but that had a very strong relationship to what we do live.

To me, it seems like there’s a greater emphasis on vocals and singing this time. Would you agree with that assessment?

BPB: I would agree. Emmett and I have done a lot of singing together now, and with the Wonder Show of the World shows, we went out just the two of us to a bunch of venues that didn’t have sound systems and where we were heavily reliant on our voices. Angel Olsen came on when we wanted to perform a record we didn’t make, this album by Kevin Coyne and Dagmar Krause called Babble, which we toured last year. We needed to find somebody who could do Dagmar Krause’s part, and Angel Olsen is a phenomenal singer. She is a dedicated vocalist, meaning she’s not standing there with a guitar or a flute or a fiddle in her hand—she’s just singing. My greatest joy and greatest concern in a song is the singing, and all of a sudden, there’s somebody there who is dedicated to the singing. Right before we went in to make Wolfroy Goes to Town, Angel, Emmett and I toured the state of Florida, playing free shows at radio stations and record stores, once again with poor or no sound systems, primarily to work on the singing of these new songs. So there was an opportunity to dig into three-part vocal harmonies. Two records ago, on the Beware record, there was a lot of group-singing. That was with a group of musicians including Emmett that had toured together, but hadn’t played the songs. So there was more of a group chorus going on, because we knew each other’s voices and how to work together, but hadn’t worked on the songs. This was the first time that three singers had actually sung the songs many, many times before recording them.

The title almost seems like the title to a short story. Do you see there being a narrative or an overriding concept?

BPB: The record strikes me as kind of serious. It is important to me to not take for granted how great our job is, what we get to do with our lives. We should appreciate being able to make music and travel around. So to some extent, making a record that is kind of serious in this way, the idea of “going to town” is like painting the town red or at least putting on your nice clothes and being serious, but also being aware that you might be getting into something over your head. When someone goes to town, you also get the sense that they are oblivious to the fact that they are over their head. I wanted to note that there’s a degree of naivety or obliviousness that goes into what we do.

Like on “New Tibet,” you seem to have never shied away from using ribald language, but I was wondering if it was a conscious device for you to juxtapose a beautiful melody and coarse language. I mean, is that something you do purposefully?

BPB: I don’t think I’ve used coarse language in a song in awhile, and in this instance, it’s definitely used in a way that I haven’t used before. It’s also interesting to me that the structure of that song changed so that verse, which was later in the song, in the end got moved to right at the beginning of the song. It’s an image and an act that for a variety of reasons needed to be conveyed, at least in so far as the needs of the song. You couldn’t say “as boys, we had sex with each other.” It’s not very musical. There’s the potential for the word “fuck” to inherently be conveyed with anger and it wasn’t supposed to have anger in it. Having Angel’s voice was a way to diminish certain kinds of powers the word can hold to let the other powers rise up. That’s why it’s, as you say, a beautiful melody, to say, “We don’t mean fuck in this way, we mean it in this way.”

Despite the various name changes you’ve gone through over the years, your aesthetic has been fairly consistent. I’m curious if you’ve had the urge to break away from that style and, I don’t know, make a hardcore record or something.

BPB: The urge is one thing, and the ability is another. But yeah, in the ’90s, there was that Traci Lords sort of house dance music, and I thought, “God, I’d love to make a record that sounds like that!” But I can’t make a record that sounds like that. It’s been so awesome the few opportunities I’ve had to do something else. There’s this guy Chris Vrenna, whose musical project was called Tweaker. He’s a drummer, and he’s drummed with Gnarls Barkley and before that Nine Inch Nails. He made these two solo records and he asked for various people to contribute lyrics and sing those lyrics on his record. It’s kind of pop industrial music, like Nine Inch Nails is pop industrial music. It was awesome because I got to participate in music that sounded differently. I didn’t have to necessarily change my aesthetic, it was just a different collaborator.

David Pajo and I did some music for the short film Slitch by Diane Bellino, and she needed some punk rock because that’s what the main character was listening to. So we wrote two punk rock songs that were heavily Misfits-influenced. That was good, but it’s not something I feel I could pull off. Providing the vocals for the Björk song (“Gratitude”) for the Matthew Barney movie Drawing Restraint 9 is in many ways a significantly different approach or sound, but I couldn’t do it on my own. We’re limited to our own skill sets, I guess, and should be grateful for it.

Talking about movies, I hear you’ve been working on something with David Byrne for a film.

BPB: Yeah, we did do something together. He was asked by an Italian director (Paolo Sorrentino) to make music for his movie (This Must Be the Place), and in addition to the score, he was asked if he would write songs for a fictional band in the movie. In the screenplay, the band’s music was identified as sounding like, among other things, my music. So he contacted me and said, “Listen, I’ve got this job. I’m supposed to make music that sounds like your music. Do you want to do it?” And I told him, “That’s very nice of you to ask, but they did ask you, so what if we cowrote the songs together?” That’s what we agreed to do, so he wrote the music and I wrote the lyrics for four or five songs and those are meant to be the songs that this fictional band plays in the music.

Do they lean more towards what you do or do they have the multi-culti, world flavor of his music?

BPB: He was the authority on this job, but knowing the original instructions, I wondered sometimes because the sound was more David Byrne than Bonnie “Prince” Billy. But I felt like this was kind of a gift horse—it was definitely financially a gift horse. It was such an odd opportunity for a collaboration, I just decided that I was going to expand upon what I was asked to do and not comment on what I was not asked to comment on. But yeah, the sound is probably more akin to a David Byrne solo record than any sort of Bonnie “Prince” Billy I’ve ever heard.

You’ve been performing under Bonnie “Prince” Billy for a long time. Has it developed as a character that is separate from yourself?

BPB: It began as a character that is very separate from the physical self, who is able to speak on telephones and such, and has maintained that for the most part. Once the voice is lifted up into song, it’s a different thing all together, so it can’t be a human being singing those things.

Judging from other things I’ve read, by your own admission, you stumbled into making records. Was there a specific point or album where you felt like you had found your voice?

BPB: It was different records, but I guess the biggest ones would be Arise Therefore and I See a Darkness, in terms of discovery of a voice. Arise Therefore had a consistent voice and there was a sense of achievement because it was a record I made with my older brother, David Grubbs and Steve Albini, who were big influences and musical heroes. There was a consistency to the songwriting that I felt hadn’t been there before. It was a record that was made deliberately, where the records before that had been like, “Wow! Whoa, what are we going to do now? Let’s do this. Okay, that’s a song.” Arise Therefore wasn’t like that. It was very methodical and deliberate. But then it was like, “Now that I have this voice, is that the voice I want? No, there needs to be something more romantic, more adventurous. What is that?” Then it took the record Joya before I finally landed on Bonnie “Prince” Billy. And that’s where we—the royal “we”—are today.