One morning, LaMontagne heard the Stephen Stills song Treetop Flyer on the radio as it awoke him at 4am for an early work shift at a shoe factory. After purchasing the acoustic Stills Alone album (1991), LaMontagne decided to quit his job and begin a musical career.
He has since released two albums, Trouble and Till The Sun Turns Black. Bootleg copies of his early demo albums Raycharles LaMontagne (1999), Acre of Land (2001), Green (2002), One Lonesome Saddle (2002) and Introducing Ray Lamontagne (2003) are also now in circulation. In the UK, Trouble was a top 5 hit, and the single of the title track was a top 25 hit. Till the Sun Turns Black was a top 40 hit in the US. He has also recorded two popular B-Side covers of Gnarls Barkley's Crazy and his original song, Jolene, which can be heard in the closing credits of the 2010 movie The Town[i].
Musically, Ray plays guitar, harmonica and piano, but he is particularly known for his raspy voice, which has been said to [i]"combine the soul of Ray Charles and the grit of Otis Redding". Whilst LaMontagne says he is highly influenced by Stephen Stills, critics have compared LaMontagne's music to that of Van Morrison, Nick Drake, and Tim Buckley.
LaMontagne is a soft-spoken, notoriously private person who shuns the media spot-light, rarely giving interviews. He rarely interacts with the audience during his live shows and has even been known to perform live shows in the dark in order to separate himself from the audience.