Believe it or not, it is possible for a singer-songwriter to be too sensitive for his own good. Take the case of Wilton, Maine’s Ray LaMontagne. An intensely private individual who prefers the solitude of the country to the rush of big cities, he found himself literally incapable of talking to people for a couple of years a decade ago, withdrawing from the world and into himself. While the 32-year-old is considerably better today, it’s somehow amazing that he’s able to stand on-stage in front of an audience. Reached at a San Diego tour stop, LaMontagne hints that, in many ways, he’s no less tortured than he’s been during the darker periods of his life. What gets him through the rough patches these days is having an outlet for his angst.

“I reach for my guitar when I’m a mess,” LaMontagne says quietly. “That’s what helps when I’m trying to figure something out.”

As has been noted in every article written about him, LaMontagne was toiling away in a shoe factory in the early ’90s when, after hearing Stephen Stills’s “Treetop Flyer” on early-morning radio, he decided he was meant for something other than the 9-to-5 grind. His subsequent foray into the world of pop music has proved not only therapeutic, but also increasingly financially rewarding. With little mainstream airplay, his stripped-down 2004 debut, Trouble, eventually shipped over 250,000 copies at home, with fans won over by the singer’s black-hearted take on contemporary MOR. If a 2005 appearance at the Bonnaroo Music & Arts Festival elevated his profile among jam-band aficionados, having Taylor Hicks perform “Trouble” on American Idol helped introduce him to mainstream America. LaMontagne admits that going from a nobody to a just-under-the-radar phenomenon has taken some getting used to.

“Touring and playing has been hard for me, but it’s also been rewarding,” he relates. “It’s getting better all the time because I’m more in control of things now—things like sound and lighting. And I’ve also got a really great band finally. All that kind of stuff makes things easier.”

LaMontagne’s latest, Till the Sun Turns Black, proves the singer isn’t content to make the same record twice. Thanks partly to producer Ethan Johns, the disc has an unmistakable, genre-spanning ambitiousness, with “Be Here Now” buoyed by symphonic string swells, “Barfly” serving up classic soul–drenched R&B, and “You Can Bring Me Flowers” smelling like fall in the Mississippi Delta. Tying things together is the album’s dark and smoky other-side-of-midnight vibe.

“I wanted something that sounded very complete from start to finish, both thematically and sonically,” LaMontagne says. “This was a real attempt at doing something that would draw you in from the first song, take you somewhere for 45 minutes, and then let you off the hook at the end.”

If the journey on Till the Sun Turns Black isn’t exactly an uplifting one, that shouldn’t come as a surprise. Asked what frame of mind he was in during the writing process, LaMontagne makes it clear that, even as many are pegging him to blow up as the next Ben Harper—or at least the next Jack Johnson—he’s still got the kind of troubles that can make getting up in the morning a struggle.

“When I look back at when I was working on Till the Sun Turns Black, it was sometimes painful, sometimes good. Those kind of swings are, I think, something that everyone goes through. I guess I’m just like everybody.”

Well, not quite. But even if he never gets James Taylor–icky in his lyrics, LaMontagne obviously has the right stuff for entry into the sensitive singer-songwriter club.

Ray LaMontagne plays the Centre in Vancouver for Performing Arts tonight (November 16).