Born in California but raised in Hudson, Québec, Watson attended Lower Canada College. He began his musical career in high school as a member of a ska band called Gangster Politics. He subsequently left the band, and released his own solo debut, Waterproof9, in 2001. He has toured with John Cale, The Cinematic Orchestra, Amon Tobin, The Dears, Feist and James Brown.
He received a nomination for New Artist of the Year at the 2007 Juno Awards, as well as winning the second annual Polaris Music Prize.
He co-wrote and performed on several songs on The Cinematic Orchestra's 2007 album Ma Fleur including the opening track "To Build a Home". His "Missing You" remix of Champion's "Guy Doune", from Champion's 2006 album The Remix Album, reached #1 on CBC Radio 3's R3-30 chart in early 2007.
Some of their tracks have appeared in mainstream media, such as Grey's Anatomy and MTV Diary. In 2008, Watson composed the entire soundtrack for the French-Canadian film, C'est pas moi, je le jure!.