Raymond Charles LaMontagne (pronounced la-mon-tayn) was born in June 1973 in Nashua, New Hampshire. His mother moved her 6 children wherever she could find work, so it was difficult for LaMontagne to make friends during his childhood. In addition, he frequently ditched high school classes, instead writing stories or getting into fights with other students. As a result of these interactions, his grades were poor, and he barely graduated, but after graduation, LaMontagne moved away from his family to Lewiston, Maine in order to find a full-time job, which came at a shoe factory where he worked 65 hours a week. One morning at 4am, LaMontagne heard Stephen Stills' song "Treetop Flyer" on the radio as it awoke him for an early shift, and after purchasing the “Stills Alone” album, he decided that he wanted to quit the shoe factory and start a career as a singer-songwriter.

LaMontagne began touring in 1999, whilst maintaining a side job as a carpenter, and in the summer of 1999, he had amassed 10 songs for a demo, which he sent to various local music venues. Mike Miclon, the owner of Buckfield Maine's Oddfellow Theater heard the demo and invited LaMontagne to open for folk acts such as John Gorka and Jonathan Edwards. A friend and business executive heard LaMontagne’s recordings and introduced him to Jamie Ceretta of Chrysalis Music Publishing. With the help of CMP, LaMontagne re-recorded debut album ”Trouble” at Sunset Sound in Los Angeles, California with producer Ethan Johns in 2 weeks, and CMP sold it to RCA Records in the US and Echo Records in the UK. It was released in September 2004, peaking at number 189 on the Billboard 200, but selling over 250,000 copies, and more than 400,000 worldwide. It proved a slow burner - in 2006, the single "Trouble" became a Top 40 hit in the UK, and the album of the same name peaked at number 5 on the UK Album chart. He won 3 Boston Music Awards in 2005 for "Album of the Year" (”Trouble”), "Song of the Year" ("Trouble"), and “Best Male Singer/Songwriter”, and was named "Best New Acoustic Rock Artist" at the 2005 XM Nation Awards.

LaMontagne’s second album, “Till the Sun Turns Black”, also produced by Ethan Johns, was released in August 2006, featuring singer-songwriter Rachael Yamagata providing background vocals on the song "Barfly." The album peaked at number 28 on the Billboard 200 album chart, selling 28,000 copies in its first week of release. The album also sold enough copies to be a Top 3 Heatseeker album in New Zealand.

LaMontagne released his third studio album, “Gossip in the Grain”, in October 2008 on RCA Records. Working again with producer Ethan Johns, the album also featured LaMontagne’s touring band, with Johns himself on drums, Jennifer Condos on bass, and Eric Heywood on guitar.