It all started when Ray heard Stephen Stills' "Tree Top Flyer" on the radio. The song amounted to an epiphany for LaMontagne, and he made up his mind on the spot to become a singer and musician. By the summer of 1999 he had put together a ten-song demo tape of his songs. Chrysalis Music Publishing house signed the young songwriter and teamed him with producer Ethan Johns in the studio, resulting in LaMontagne's debut album, Trouble, which was picked up by RCA Records and released in the fall of 2004.
With a voice that sounds at times like a huskier, sandpaper version of Van Morrison or Tim Buckley and a tight, emotional writing style, LaMontagne impressed critics with such songs as the title tune, "Trouble," and the cinematic style of pieces like "Narrow Escape".