Drew Gregory grew up on a fifth-generation family farm in the heart of the Canadian prairies, where the cycles of planting and harvesting profoundly shaped his understanding of life’s rhythms. This perspective informs his songwriting, which is infused with down-to-earth charm, grit, and honesty. His music bridges modern country production with classic storytelling, crafting vivid portraits of everyday life that resonate deeply with listeners.
His latest single, “This Side of the Dirt,” captures this essence with its lively, uplifting energy and irresistible dobro riffs. Co-written with hit songwriter Wade Kirby and mixed by Grammy-winning engineer Chad Carlson, the release follows a string of accolades, including Drew’s 6th Alberta Country Music Award. A rising star in the Canadian country music scene, Drew has performed at prestigious festivals like the Calgary Stampede and Country Thunder, sharing stages with icons such as Miranda Lambert and Kip Moore. Known for his magnetic stage presence and authentic connection with audiences, Drew continues to deliver music that celebrates country living and the simple joys of life.
Name:
Drew Gregory
Genre:
Country
Founded:
2009
# of Albums:
7
Latest Album:
One For The Road
Latest Single:
One For The Road
Latest Video:
Favourite musician growing up:
I was always a fan of music that straddled the line between country and rock and roll. We listened to a lot of Blue Rodeo, the Eagles, and Jon Mellencamp, and I was always drawn to that.
Favourite musician now:
Eric Church is the artist that really got me into songwriting and does a great job of tying in those rock and roll influences into the country world.
Guilty pleasure song:
Brand New Man on the Brooks and Dunn Reboot 2 Album with Warren Zeiders. Very unexpected but interesting twist on a classic!
Live show ritual:
If I can get a post soundcheck nap in it sure helps. We don’t get to sleep through the night very often. Right before the show I jump around a bunch. Get the blood going then run on adrenaline the rest of the show!
Favourite local musician:
Devin Cooper he’s bringing a lot of rock and roll back into the local country scene!
EP or LP?
EP for online, put a few EPs together for an LP on vinyl.
Early bird or night owl?
Definitely a night owl.
Road or studio?
Definitely the road. Every bit of energy I put into the music industry is in attempt to get back to the stage!
Any shows or albums coming up?
New album out Feb 21. We have a live taping of Stampede City Sessions at Webber Academy in Calgary on March 22nd, which will eventually air all across North America!
Where can we follow you?
Instagram | Facebook | Apple Music | YouTube | Spotify | TikTok | Linktree | Website
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Rapid Fire Local Questions:
What is your favourite local restaurant?
King Eddy in Calgary. Great food and live music!
What is your favourite street in your city and why?
The road leading out to our farm for me. It’s exactly what the new song One For The Road is about, and you’ll have to listen to find out why!
What is your favourite park in your city and why?
Can I say Stampede Park during Stampede? We get to play there quite often and theres an amazing energy in every corner for those 10 days in July!
What is your favourite music venue in your city?
I said King Eddy for food but we’ve always loved playing in at Ranchmans. It also has a great energy and the show we put on very much match’s the vibe there.
What is your favourite music store in your city?
Turn It Up! Records and Hifi. Great vinyl selection and I’m big into the vinyl!
