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About Drew

There is an authenticity and truthfulness to the music of Drew Gregory that is undeniable. The songs of this award-winning Alberta country music sensation are infused with a down home realism, a gritty honesty and 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 and amiable coin, solidly rooted in the landscape and soil of his rural homestead. The music is as approachable as he is, something that also translates on stage as he forms an instant rapport with any audience for whom he performs.

Growing up in the small rural community of Standard, Alberta (population around 350) Gregory was exposed to music through local radio as well as from his dad’s extensive classic rock vinyl collection, and soon came to appreciate both 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 was going to be a big part of his life.

Evidence of Gregory’s status as a country music artist on the rise are the numerous accolades that he has thus far garnered in his career. Most recently, he was named Country Music Alberta’s (CMAB) Male Artist of the Year at the 2019 awards and took home the 2019 CMAB Award for song of the year. His single Better in A Bar won that title, a song he penned with long-time co-writer Aaron Goodvin. Over his burgeoning career he has shared the stage and opened concert and festival dates for the likes of Miranda Lambert, Kip Moore, 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 (both Main Stage and Molson Stage), Bud Country Fever, Country Thunder 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 from 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.

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