Ray LaMontagne

True to its title, a lot of hard times went into Trouble — Ray LaMontagne’s bar-setting debut — from a childhood spent in different cities with his single mother to the constant struggle that was high school. (When he wasn’t getting into fights, LaMontagne was skipping class.) All of that pain makes for great art, however, as the singer-songwriter lets his grainy but gorgeous voice soar over sweeping strings (the title track), a spare acoustic (“Hold You In My Arms”), hollow drum beats (“Forever My Friend”), and Skynyrd-schooled Route 66 riffs (“How Come”). That’s just the beginning, too. Slide on over to our Next Steps and you’ll find a hefty handful of live cuts and key tracks from three other albums.

Ray LaMontagne’s always been the quiet type, especially at his incredibly intimate shows — sets that don’t bother with small talk. They cut straight to the bone instead, whether we’re talking about the sunset balladry of “Achin’ All the Time,” the crowd-pleasing chords of “Burn,” or a chilling Bob Dylan cover (“Masters of War”) that’s led by Gov’t Mule frontman Warren Haynes. As for LaMontagne’s studio albums, they push his wounded words up front alongside lonesome lap steel guitars (“This Love Is Over”), carefully brushed cymbals (“A Falling Through”), and misty-eyed effects (“Within You”).

The story’s too good to be true, but guess what? Ray LaMontagne really was working in a shoe factory when he heard Stephen Stills’ “Treetop Flyer” single and decided that playing folk music wouldn’t be such a bad gig after all. Since then, LaMontagne’s spine-tingling songs have ended up on everything from I Love You, Man (the horn-blasted, soul-infused “You Are the Best Thing”) to Rescue Me (the simmering, sustained notes of “All the Wild Horses”). That’s because his tenderized tunes were tailor made for campfire confessions and thinking about it all until the sun comes up — like Tim Buckley after one too many whiskeys, or Iron & Wine on a road trip to nowhere.