Orlando gets a chance to spend 'An Evening With Bonnie "Prince" Billy' at the Dr. Phillips Center

Will Oldham hasn't played Florida for over a decade. His last jaunt through the Sunshine State was a grassroots string of smaller performances at record stores and radio stations.

Part of that jaunt included a mystical set at Orlando's own Park Ave CDs exchanging vocal harmonies with Angel Olsen as a live workshop of sorts for the songs that would make up the bulk of his 2011 album Wolfroy Goes to Town.

But for this tour supporting his latest record, Keeping Secrets Will Destroy You, we find the restless artist playing a slightly more luxurious but no less intimate space in the Alexis & Jim Pugh Theater at the Dr. Phillips Center this week.

Oldham released his first album, There Is No-One What Will Take Care of You, in 1993 under the Palace Brothers moniker, releasing four albums under that name or as Palace Music before settling on the Bonnie "Prince" Billy persona for 1999's release I See a Darkness. This album still serves as a primer for the nuanced, raw and achingly beautiful music he has continued to make throughout his career.

With 19 official albums as Bonnie "Prince" Billy, Oldham has amassed a catalog rife with intricate vulnerabilities and hard-won, though cryptic, wisdom about the human condition. Oldham has been often cited as a leading light of the No Depression alt-country movement along with fellow travelers Smog, Lambchop and Neko Case, sharing a sparse, literate and incisive approach to songwriting.

These same qualities have garnered him comparisons to Southern Gothic writers Flannery O'Connor and Carson McCullers. For his part, Oldham is less than certain about these parallels.

"When you talk about Southern culture or Kentucky, I can only say it is about being who we are, or rather, who I am. There are no intentional stylistic approaches; I don't know how to play another instrument besides a guitar. I am trying to explore interpersonal connection more than the fundamentals of music," muses Oldham. "Our community is those other pieces of work, which makes for an interesting grouping of voices. These voices are honed primarily internally but with the guidance of these other available texts."

The albums that make up the Bonnie "Prince" Billy discography are organic cosmologies of the inner workings of his songs' protagonists. His lyrics have an unadorned honesty and deceptive simplicity that invite the listener into a conversation about humanity that often measures its heaviness with a knowing humor.

"I am trying to put as much heart, as much content and as much work into these songs as possible and to augment these consolingly or comfortingly intimate meditative songs to build communion and connection," explains Oldham of the writing of his latest record. "That is where the logic of these songs exists, and that is a vital and crucial space.

"I try to make songs that are open to a kind of welcoming or a kind of interpretation where people will find themselves throughout the song and recognize their relationship to the song and why they would want to hear it again and why I would want to sing it again. Ideally, it is about singing about something we share."

The attempt to create something that both the artist and the audience can share extends to how Oldham builds his live performance. Oldham works from a body of songs that can be tailored to the atmosphere of a space, an audience and an evening, rather than being tied to an inflexible setlist.

"That's part of the goal, to see someone who is fluent and comfortable in what they are doing," says Oldham. "There is all this work that goes into this, so that in that moment you can experience and communicate and feel free."

And really, when you get down to it, who doesn't want to feel free?