Drew Gregory grew up playing guitar for his friends in a small Alberta farming town, and recorded his first EP as a Christmas gift for his mother. But as a result of a trip to Nashville, Tenn., he can now be heard on radio stations throughout the country.
Raised in Standard, Alta., Gregory recalls his high school graduating class having only 21 students, nine of which had been together since kindergarten.
They were what he calls a “pretty tight-knit group.”
It was in junior high when Gregory first became interested in learning to play the guitar.
“I was hanging out with a friend of mine, she had a guitar sitting in the corner and every time I was over there, I was just playing it all the time.”
After a while, that friend suggested that he get a guitar of his own.
Gregory recalls it being a funny situation because his parents had just bought his sister a $2,500 piano, but were only willing to split the cost of a $300 guitar starter package with him.
On the other hand, singing came much later for Gregory. It wasn’t until after college that he started to take it more seriously. Having moved in with a friend who worked into the night, Gregory had lots of time to practice and be as loud as he wanted.
“Shortly after starting to sing out there, I started writing my own songs and started kind of thinking about the whole thing as a career,” he recalls.
The first songs Gregory ever recorded were meant to be a Christmas gift for his mother. It was just simple acoustic renditions of some songs he had written. However, once word got around that they had been recorded, many more people were interested in getting copies for themselves.
It wasn’t long after that Gregory decided to make his first trip down to Nashville, in 2009.
He remembers flipping through a road atlas that his friend had brought home one day, looking for a fun road trip to take. They then came across Tennessee, and Gregory says that is what put the bug in his head to go down there and give music a try.
Upon heading to Nashville, Gregory began looking for accommodations and decided to stay in a hostel.
“There was a hostel in Nashville, so I thought I would try it out and honestly that was a great move too. I met so many musicians staying there.”
During the three months that he was there, Gregory had the opportunity to jam with other musicians every night and play a few open mics. The hostel where he was staying even had a board listing all of the open mic opportunities and places to visit for singer-songwriters.
While in Nashville, Gregory decided to join the Nashville Songwriters Association International and later found out they had a chapter in Calgary.
“When I was leaving, I heard the interview the whole drive home and then heard the song for the first time. Something you never forget for sure.” – Drew Gregory
It was at one of these chapter meetings where Gregory learned about the Rawlco Radio 10K20 grant — a contest where the winner receives $10,000 to put towards their career.
Gregory applied for the grant with the acoustic songs he had recorded and went on to win the money, putting it towards recording his debut album, Country Hurricane.
“[I] put that album out and that’s the one that really, I think, solidified I can do this, this is going to be a career thing.”
Not too long after releasing the album, Gregory met his now long-time manager, Angie Morris, at a songwriter’s night in Calgary.
“I was actually in there with another artist I was working with at the time and they were sharing the stage,” Morris recalls, adding that she was drawn to Gregory because of his unique vocals. “I thought he’s really got something special.”
As a result, she approached him about working together and eventually suggested that he put his music out to radio.
“If an artist is going to pursue a career in the industry, you need [songs on the] radio.”
Gregory remembers first hearing his music over the radio on High River’s station, Sun Country 99.7 FM. They had brought him in to record an interview and get to know him better.
“When I was leaving, I heard the interview the whole drive home and then heard the song for the first time. Something you never forget for sure.”
Since that debut album, Gregory has had the chance to record many more projects, play countless shows and even win a few awards.
The majority of Gregory’s shows have been played alongside award winning guitarist Mitch Jay.
When asked about the most memorable shows they’ve ever played together, Jay said, “I’ve always had a really good time playing with him at the CCMAs. We’ve done some acoustic showcases out there, and we’ve always roomed together. It’s kind of a fun weekend away.”
Some other highlights of Gregory’s career include playing on TV for 2.7 million viewers on CMT, and getting the chance to perform at Big Valley Jamboree and Nashville North during the Calgary Stampede. Some of the awards that he has won include Male Artist of the Year at both the 2015 Alberta Country Music Awards and the 2016 YYC Music Awards.
Gregory’s latest single, Smokin’, was co-written with country star Aaron Goodvin, and recorded with renowned country musician and producer Jason Barry.
When asked about writing with Goodvin, Gregory said, “It was cool! That was before he was all big and famous now too.”
“He’s great, man, I’ve been great friends with him for a long time. He was one of my first connections, again, in Nashville.”
Gregory went on to say that his latest single came about after the two of them, along with another songwriter friend, got together late on a Friday night. The three of them then decided to write a song and see what they could come up with, and Smokin’ was born.
Currently working on a new album, Gregory says he’ll be “going down to Nashville right away here again in the winter, trying to finish up writing.”
Gregory hopes to release his new music by mid 2018.
Editor: Jolene Rudisuela | firstname.lastname@example.org