top of page
  • Annette Dawm

Drew Gregory Has Found a Good Place to Start

Drew Gregory has been part of the Canadian country music scene for many years now. However, it almost feels as though he’s had a new beginning with his latest album, Good Place to Start. With the help of his fans, the album went to number one on the iTunes country chart the day it was released.

“That was such an incredible feeling,” Drew explained. “I wasn’t sure if we’d get there with Dierks Bentley having released [his new album] not too many days before.” While driving to his own album release party, Drew received the news that he did in fact make it to the top of the chart: “I had to pull over. It just hit me so hard. So much work and so much sacrifice goes into an album-- as any musician knows-- and I feel we worked on this one and did more promo on this one than any in the past. So, to get the number one status and be validated for the work we’d done felt pretty amazing!”

The title track of the album centres around the shootings that occurred in Las Vegas. Right away, Drew and his team knew they had something special during the writing and producing process: “I’m sure we’re not the only ones who wrote about that tragic event but I think any time a songwriter or group of writers get together after something like that, it’s going to come out in our lyrics. It felt like something that needed to be said…. I think I love the song so much because it doesn’t pick a particular side. It just says maybe every side could show a little more love towards one another and maybe listen a little bit more and there would probably be a lot less trouble in the world.”

Initially, Drew found a good place to start his career outside of Alberta on a reality show called Big in a Small Town, which aired on CMT Canada in 2012. When asked why he chose to audition, Gregory admitted that the name of the show had a lot to do with it: “I’ve always had an entire small town community behind me, especially early in my career, which really helped launch me. I think the national exposure from that show was very helpful in breaking me out of the small town bars and into some big venues across the country!”

Throughout his career, Gregory has strived to keep his music “real and authentic” while also maintaining his family farm. “I grew up on a farm just outside a small town and still work there with the family so every time the lyrics in the songs talk about that stuff they have come from a real place and real experiences.” He added that “it can be hard” to balance both a music and an agricultural career, especially in the summer. Luckily, he has great support systems in both fields. “My family has always been very helpful if I have had to leave the farm at a certain busy time for music.” He also credited his long-time manager, Angie Morris, who “always helps take a lot of the business side of things off my plate when duty calls at the farm.”

With regards to his songwriting abilities, Drew doesn’t think of himself as a great songwriter yet, but he knows what it takes to get there: “I think you really have to write from the heart. I know it sounds cliché,’ but I think it’s so true. Fans (especially of country music) can tell when something comes off as fake. I think practice is also important. No one’s first song was ever a hit. I’ve learned a lot over the years and still consider myself far from a great songwriter but I’d like to think I’ve gotten closer…. I think when I started out in this business I just wanted people to be happy. I wanted to help them get over heartbreak or help get them pumped up for a night on the town or maybe laugh at themselves or maybe just feel a little more love in their hearts. I try to touch on a bunch of different emotions on every album and I think there’s something for everyone in many different situations … but I hope at the end of each song, they have a smile on their face!”

Having just wrapped up a series of shows at The Calgary Stampede, Drew said, “I can’t think of anywhere else in the world where live country music plays such an important role for 10 days straight! Everyone appreciates the live music so much and there is such an incredible buzz everywhere in the city the whole time.” When asked what else he is looking forward to this year, he replied, “We are back at the Big Valley Jamboree this year. To this day, one of my favourite shows ever has been the first time we played there. We also are on the Main Stage at Country Thunder (Alberta) before Dierks Bentley this year which will be a career highlight for sure!”

Finally, Drew Gregory offered his advice for others who are also looking for a good place to start in the music industry: “I think you have to be prepared to be in it for the long haul. So, if you don’t absolutely love it with all your heart, don’t expect to get to the top. There are some tough days but if you have that love and that passion for it, the music will always pull you through-- and get out there in play. I see too many sitting around waiting for that big hit. When it comes you’re going to need to be ready so make sure you play every chance you can and build some fans along the way! Enjoy the journey!”

For more information, please visit

Photo by Annette Dawm.

To see more photos of Drew, click here.

bottom of page