Bio

There is an undeniable authenticity and truthfulness to Drew Gregory's music. The songs of this award-winning Alberta country music sensation are infused with a down-home realism, a gritty honesty, and a vibrant sense of rootedness that comes from years spent working the land as a farmer – an aspect of his life that is deeply connected to his talent as a musician, singer, and songwriter.

Gregory, the singer, is also Gregory, the farmer – two sides of the same engaging, unpretentious, amiable coin, solidly rooted in the landscape and soil of his rural homestead. The music is as approachable as he is, which also translates on stage as he forms an instant rapport with any audience he performs to.

Growing up in the small rural community of Standard, Alberta (population around 350), Gregory was exposed to music through local radio and from his dad's extensive classic rock vinyl collection. He soon came to appreciate the country and rock sounds that flowed through the family home. By the time he was 15, he had acquired his first guitar, and from the first strum of the strings, he knew that making music would be a big part of his life.

Evidence of Gregory's status as a country music artist on the rise is the numerous accolades that he has thus far garnered in his career. With his most recent "Horizon Male Artist of the Year" Award from Country Music Alberta for the 2023 season, Drew marks his fourth win in this category, having also won the honour in 2015, 2019, and 2021. He also received Country Music Alberta's "Horizon Song of the Year" in 2019 for Better in A Bar, a song he penned with long-time co-writer Aaron Goodvin, and Country Music Alberta's Horizon Album of the Year for his album I Was There in 2016. Drew was recently named one of the Top 3 artists in the Project Wild Development Program in Alberta after a six-month-long journey of education and development. At the finale in Calgary, he was awarded $50,000.

Over his burgeoning career, he has shared the stage and opened the concert and festival dates for Miranda Lambert, Kip Moore, Old Dominion, John Michael Montgomery, Big & Rich, Emerson Drive, and Chad Brownlee, among others.

Drew feeds off and reciprocates the energy of a crowd better than any and has plenty of experience on stage for large and smaller audiences. Past festivals include The Big Valley Jamboree (Main Stage and Molson Stage), Bud Country Fever, Country Thunder in Calgary and Arizona, and Dauphin Country Fest. Drew made his debut appearance on the Nashville North stage during the 2015 Calgary Stampede and has been a staple every year since. His performances at clubs, rodeos, and festivals tend to draw large crowds after years of being a reliable high-energy show. Even though he's a small-town farm kid at heart, he is more at home on stage than anywhere else.