In the music world, there are the true eccentrics (folks whose strange personas are vindicated by their work) and the willfully obscure (those who cultivate an air of strangeness in a calculated bid for artistic respect). In the case of Bonnie “Prince” Billy, a.k.a. Will Oldham, it’s been difficult at times to tell which side of the line he’s on. The teenage indie-film actor featured in John Sayles’ 1988 film Matewan, he went on to become ringleader of the influential ’90s indie-folk outfit Palace and continues to assume any number of personas.

Thanks to his cryptic lyrics and public statements, cynics have suggested Billy has cultivated more than just his legendary beard. In the process, though, they have dismissed one of the more vital American songwriters of the past 20 years, an odd yet undeniably talented musician whose songs even attracted the attention of Johnny Cash during his final years.

Certainly Billy’s mercurial public persona has added to the speculation. He’s at turns affable and testy: Some journalists have been audience to Billy expounding on the appeal of R. Kelly’s music (a recurring Billy obsession that culminated with an appearance on last year’s Trapped In The Closet reprise and a cover of “The World’s Greatest” on Ask Forgiveness, a 2007 covers album he released as Will Oldham). Less fortunate reporters have received the sort of taciturn and combative treatment that Bob Dylan refined to an art. But as Dylan once insisted, such a public persona was meant to turn the public eye away from the persona and toward the musical output, and Billy expresses a similar sentiment.

“The easy way to maintain an ‘elusive’ profile is to not engage in the things that would destroy privacy,” he explained in a 2006 interview. “The majority of the people on the planet do it effortlessly. It is my hope that the music can be very public while the figures who make it remain unimportant to its fullest appreciation.”

The music certainly stands up on its own merits, chilling character studies that possess all the bleakness of Appalachian murder ballads. 2006’s The Letting Go was a chilling exploration of loss, a set of songs that took on increased resonance when Billy released the demos he recorded with Faun Fables’ Dawn McCarthy as a limited-edition CD, Wai Notes, in late 2007.

The Letting Go boasted a cinematic scope, adorning the skeletal arrangements documented by Wai Notes with an orchestral string section. Still, it’s not surprising that Billy would return to the tapes and re-release the tracks in their formative stages — when I interviewed him around the release of The Letting Go in late 2006, he emphasized his fascination with recording and performing as a collaborative process.

“It is all about what is possible,” he noted about the process behind recording The Letting Go. “I had traveled with my cousin Ryder McNair, and he had played me some orchestral pieces he had arranged. As I was putting the session together, I called Ryder and warned him that I might be calling on him to write some arrangements. I want to keep instruments, friends, voices, arrangements, family, songs, time, as intertwined as possible. It isn’t really hashing-out; it’s the design of what is to occur; I guess it gets hashed out primarily inside of everyone, and it’s about turning brains inside-out. The exception would be Dawn McCarthy’s input. She had pretty much lined out her arrangements prior to the session itself, and was able to mold them to the forms we mutated.”

It’s tempting to read Billy’s songs as autobiographical: They are usually written in the first person, and he clearly demonstrates his ability to inhabit the minds and souls of the characters that drift through his songs. But he dismissed any suggestions that these characters are a stand-in for himself, insisting “the songs are evidently not an illustration of the perceived life of the man singing.” And while his traditionally spare arrangements have shone a bright spotlight on his words and vocals, he also refused to isolate his songwriting process, insisting that each song is a work in progress that owes as much to the other players as it does to the songwriter. “Each performance of a song might be helped or hindered by that approach,” he explained.

Similar to the philosophy behind his recordings, Billy considers his tours a work in progress that relies as much upon his fellow players as himself. “There are tours and there are records; they are not related to each other,” he said. “There is no effort to differentiate. Live shows are fleeting and the record will last; why waste effort re-creating what has already been captured?” It’s a fleeting sentiment that perfectly embodies the engima of the singer and the man: simultaneously direct and discursive, Billy has found a way to embody many seemingly contradictory traits without betraying a hint of effort or calculation. It’s precisely what makes him a fascinating figure, but more importantly, such a compelling songwriter.

Note: portions of this feature appeared originally in the Metro Santa Cruz.