“The universe works in such strange ways,” says Ray LaMontagne, explaining his evolution from an unknown songwriter to a platinum recording artist. “It leads you down a path that you didn’t even know you needed to go down.” 

LaMontagne does do many interviews. But the soft-spoken singer-songwriter recently joined Billboard’s Behind the Setlist podcast to talk about the 20th anniversary reissue of his debut album, Trouble, in a conversation that touched on his unusual path to becoming a musician and his impressions of Trouble 20 years later.

Initially, LaMontagne expected to write songs that other artists would record. He didn’t enjoy performing live, and songwriting could give him an opportunity to make music in solitude. “That’s much more my personality — especially at that time,” he says. But his songs weren’t traditional. After recording demos, LaMontagne was told his songs were unfinished, just verses without bridges and choruses. Even though nobody wanted to sing them, he received encouraging feedback. “People are responding to you singing them,” he was told. 

With his songwriting career dashed, LaMontagne embarked on a life as a recording and touring artist. He signed to RCA Records and released his debut album, Trouble, which was given a 20th anniversary reissue on June 7. Making a record meant touring to support it. Although performing was “the most unnatural thing in the world,” says LaMontagne, he now appreciates how “having the bravery” to begin performing changed his life. “With the hindsight of twentysomething years, I wouldn’t have grown as I’ve grown as a person if I hadn’t followed it.” 

Two decades later, LaMontagne has released eight more studio albums — the latest, 2024’s Long Way Home, on his own Liula Records. The old aversion to performing live is long gone, and LaMontagne fills theaters and amphitheaters in the six weeks each year he tours. Trouble wasn’t just a celebrated collection of songs by an exciting new artist, it was an inflection point in LaMontagne’s life. “This record is important to me for that reason,” he says. “It’s the record that pointed me in this direction, and I know that’s just what I was supposed to do.”

The conversation with Behind the Setlist touched on much more: his work-life balance, living in the Berkshires in western Massachusetts, his passion for environmental conservatism and his impressions from listening to Trouble 20 years later. Listen to the entire interview with LaMontagne using the embedded Spotify player, or go to Spotify, Apple Podcasts, Amazon Music, iHeart, Podbean or Everand.