Drew Gregory

Drew Gregory was born and raised in the heart of the Canadian prairies, where the rhythm of planting and harvesting on his fifth-generation family farm shaped his understanding of life's ebb and flow. This grounded perspective ultimately found its way into the heart of his songwriting, infusing his music with down-to-earth charm, grit, and honesty.

Drew's music reflects a genuine connection to his surroundings, blending modern country production with classic country storytelling to create a sound that is uniquely his own. His lyrics paint vivid pictures of everyday life, celebrating the highs and lows with equal sincerity, creating an instant bond with listeners. His distinctive sound and perspective have earned Drew a dedicated fanbase and numerous awards since he launched himself onto the Canadian country music scene.

His latest single, "This Side of the Dirt," is a lively, uplifting country rocker that blends music, melodies, and instrumentation flawlessly. With a catchy dobro riff setting the tone, you can easily picture yourself cruising with the windows down and cranking the volume to sing along to this catchy tune.

Co-written with hit songwriter Wade Kirby (Blake Shelton, George Strait) and mixed by Grammy-winning engineer Chad Carlson (Taylor Swift), the song’s release comes on the heels of his 6th Alberta Country Music Award. Drew has won the Horizon Male Artist of the Year Award a total of four times (2015/2019/2022/2024), as well as winning Horizon Album of the Year in 2017 for “I Was There”, and Horizon Song of the Year for “Better In A Bar” in 2019.

Drew’s status as a rising star is further evidenced by his repeated invitations to perform at high-profile country music festivals, including the Calgary Stampede (Nashville North Stage) Big Valley Jamboree, Country Thunder in Calgary and Arizona, and Dauphin Country Fest. Drew has also shared the stage with such artists as Miranda Lambert, Kip Moore, Old Dominion, Big & Rich, Emerson Drive, Chad Brownlee, and numerous others.

His ability to connect with his audience is unmatched, blending his down-home charm with an infectious energy that spreads like wildfire among his fans. Onstage, Drew feels completely at home, playing off the energy from the crowd and creating an electrifying atmosphere that wins over everyone in the room. Drew's authenticity, and magnetic presence never fail to leave a lasting impression.

Drew Gregory remains dedicated to his artistry, pushing boundaries, and delivering music that speaks to the soul of his listeners. With each new release, he invites audiences to join him in celebrating the essence of country living, making the most of every moment, and appreciating the simple joys of life.