Bio

Drew Gregory's music resonates with listeners through undeniable authenticity and rawness. This award-winning Alberta country artist crafts songs that reflect a deep-rooted sense of honesty and realism—qualities shaped by years of life on the farm. His experiences working the land are more than just background; they’re the heartbeat of his music and an essential part of who he is as a singer, songwriter, and performer.

As much a farmer as he is a musician, Drew brings the same grounded, approachable energy to both roles. Whether he’s on stage or out in the field, his warm, down-to-earth nature creates an instant connection with everyone he meets. His music carries that same spirit—relatable, genuine, and always inviting.

Raised in the small town of Standard, Alberta (population 350), Drew's first exposure to music came from local radio stations and his dad’s classic rock vinyl collection. The fusion of country and rock left a lasting impact. By 15, he had a guitar in his hands—and it wasn’t long before music became central to his identity.

Drew's dedication to his craft has earned him notable recognition in the Canadian country scene. In March 2025, he took home the Horizon Male Artist of the Year award from Country Music Alberta—his fifth win in the category. He also received the Horizon Song of the Year in 2019 for “Better in a Bar,” co-written with Aaron Goodvin, and the Horizon Album of the Year for his 2016 record I Was There. He was also named a Top 3 artist in the Project Wild Development Program and is a two-time YYC Male Artist of the Year recipient.

Drew’s recent releases continue to showcase his evolving artistry. His latest EP, One for the Road, is a collection of songs that balance energy and emotion, telling stories that reflect both life’s celebrations and its challenges. His newest single, Work in Progress, adds another layer of vulnerability and introspection—an honest look at personal growth that resonates with fans across generations.

Throughout his career, Drew has shared the stage with artists like Paul Brandt, Cody Johnson, Tenille Townes, Reklaws, and Jade Eagleson, to name a few. His high-energy performances have lit up major festivals including Big Valley Jamboree, Bud Country Fever, Country Thunder in Calgary and Arizona, and Dauphin Country Fest. He made his debut at Nashville North during the 2015 Calgary Stampede and has been a staple there ever since.

Despite his humble beginnings as a farm kid from a small town, Drew is at his best on stage—feeding off the energy of the crowd and giving it right back. With his latest music and a growing fan base, Drew Gregory continues to prove he's not just a work in progress—he’s the real deal.