Gregory was prematurely separated from his biological mother at approximately three months of age, with the full extent of his adoption remaining unknown until the year 1996. It was in his grade 11 math class that he first crossed paths with Jim Cuddy, a serendipitous encounter that would later blossom into a lifelong musical partnership.
Following high school, Greg and Jim co-founded The HiFis, a band that, despite its promising start, ultimately disbanded after a few years. The duo then pursued higher education, with Greg unfortunately dropping out of university.
Undeterred, they made the bold decision to relocate to New York City, where they co-founded Fly To France, a musical venture that, although successful, ultimately succumbed to the inevitable forces of dissolution after approximately three years.
Following the demise of Fly To France, Greg and Jim returned to their hometown of Toronto, where they reunited with a few close friends to form the iconic Canadian country-rock band, Blue Rodeo. As the band began working on their debut album, they laid the groundwork for a remarkable career that would be marked by numerous accolades and a lasting legacy.
In addition to his work with Blue Rodeo, Greg has also ventured into solo endeavors, releasing the critically acclaimed album, Gone.