With regard to output, collaborators and even band names, singer-songwriter Will Oldham has fostered a reputation for being dependably unpredictable. The 40-year-old Louisville native may settle upon a stable of collaborators and a moniker — like Palace or his current well-worn handle, Bonnie "Prince" Billy — for a while. But longtime fans have come to know the only thing they can take for granted is the sort of thoughtful, high-quality material that helped crystallize the '90s lo-fi movement and presaged the indie scene's ongoing fascination with the softer side of classic American Songbook tropes.
"I think I'm just doing what comes pretty naturally," says the bearded basement-folk icon. "Making music, it's nice to think you don't know what's going to happen next year, because you don't. And it's nice if your process incorporates that, rather than trying to adapt to things that aren't going to stay the same."
Oldham's little black book of partners in crime is both impressive and obscure, ranging from Chavez and Zwan principal Matt Sweeney, The Mekons' John Langford and art-flick auteur Harmony Korine to guitarist Emmett Kelly and various members of Kelly's band the Cairo Gang. "Mr. Billy" has been working with Kelly and the Cairo Gang regularly for the past couple of years, and it's a stripped-down version of this lineup that invades America's Wang™ this week for a typically atypical endeavor: a series of free shows, staged (or, rather, un-staged) at finer record stores all over the state of Florida — including Tampa's Mojo Books & Music.
Bonnie "Prince" Billy has gotten up to these sorts of shenanigans before over the last decade, launching a handful of free tours highlighting alternative venues in the U.S., and one in Northern Europe. Oldham stages these mini-jaunts before more traditional promotional commitments roll around. He doesn't consider them a return to his roots or some sort of tribute to DIY college-rock culture; for Oldham, events like the Free Florida Tour are nothing more or less than an attempt to de-formalize the connection between musician and listener. For many consumers of music, a rock show is an "event," while a trip to the used vinyl shop is as familiar as the sound of a favorite mixtape.
"That's something that always feels awkward to me about playing shows, that it's not an everyday occurrence," he says. "It's not part of your life, it's something special that you do. And it's great to think of that, but it's more important that the music is related to what you're doing. Music should be related to the lives that we lead. So it's always great if we could play a barn in Pennsylvania, or a record store at a reasonable hour, like, 'This is a part of my day.'"
"At the same time," he adds with a laugh, "if we did it all the time, we'd be broke."
It probably doesn't hurt that Oldham's timeless, deceptively low-key style seems perfectly suited to small rooms, and hushed, appreciative audiences interested in absorbing every nuance of the music. On a recent tour, Oldham was delighted to play a few shows without any amplification at all, and hopes the Free Florida Tour offers more opportunities to do away with everything extraneous to the simple transaction between music played, and music heard.
"We'll be traveling as a trio with two guitars, there'll be three of us and we won't be carrying amps, we won't have any other gear," he says. "We won't have a tour manager or merchandise, we won't have a soundcheck or collect money at the end of the night. We can play our music and explore this place ... the idea is to not be worried about the logistical things that come up [during a traditional tour]."
Oldham's description of the Free Florida Tour conjures a certain carefree vibe, a feeling of "we've gotta be at so-and-so a place at so-and-so a time, just as long as we get there" that jibes well with his journeyman persona. In fact, Drag City, the label currently responsible for releasing Bonnie "Prince" Billy material, goes out of its way to reinforce the "unpredictable" nature of the Free Florida Tour.
"I was not consulted when that was written," says Oldham. "That's based on how their experience of how our shows go anyway, but especially when there are less people involved."
Whatever the impetus, goals or execution, the Free Florida Tour offers a very special chance to catch one of America's most individual and evocative songwriters in an unbeatably intimate environment — without a green room, without four opening acts, without most of the peripheral elements we've come to accept as the necessary evils that always accompany the experience of seeing professional musicians perform live.
And, given Bonnie "Prince" Billy's in-the-moment methodology, who knows when that chance will next come around?
"If change is an inherent part of the process," he says, "the way I look at it is, you're working with change, rather than fighting with it constantly."