From Small Town Tennessee to Center Stage

Country Singer/Songwriter Drew Green Recalls His Journey to the Spotlight

A casual 350 years ago (give or take a decade or two) French writer and fabulist Jean de la  Fontaine famously penned the line: “A person often meets his destiny on the road he took to  avoid it.” 

Such a poetic statement can be applied with flawless precision to the life and career of country singer/songwriter Drew Green. 

“When it comes to doing music, I had always been told ‘Man, that’s not attainable.’ And it’s almost not. You talk about being broke, dude. You can Google me right now and it says I have a net worth of 5 million dollars. I have 5 dollars, maybe,” the 33-year-old McMinnville native tells me jokingly. “That’s why they call it ‘The Dream.’” 

Now managed by Grammy award-winning songwriter Brett James and signed to Justin  Timberlake’s Villa 40, Green’s path to the record deal of a lifetime wasn’t always obvious.  

Despite falling in love with music as a child [on his family’s tree farm in Warren County], Drew  spent much of his life walking away from that passion — while Fate made a point to tap him on  the shoulder at every turn.  

“I was in a garage band in high school,” Green shrugs. “We were pretty good; we played  Tennessee Battle of the Bands with Taylor Swift when I was 14 or something. But then we  broke up, and I didn’t play for a couple of years. I was doing college stuff.” 

It was at age 20 (with no small thanks to his fake ID) that Green was randomly discovered by  honky-tonk royalty at a local bar in Cookeville. 

“This guy came in and wanted to hear live music. Somebody there knew I liked to sing and my  guitar just happened to be in my truck, so I got up and played like 4 songs.” 

Turns out the patron wanting to hear live music was none other than the owner of legendary  Tootsie’s Orchid Lounge in Nashville. 

“He said, ‘Do you wanna sing at my honky-tonk on Broadway? I thought he was drunk, I  thought he was kidding, I didn’t think nothing about it — but somehow I got a call the next  morning asking if I wanted to come in that day.” 

Fast forward six months later and Drew decided to put down his guitar yet again, discouraged  by the long hours, minimal pay and 4 hour daily commute.  

“I went and finished school, got a job at a bank, met my wife and moved to Lebanon,” he recalls. “I worked at that bank for like a year, had just got promoted, was gonna have my own office, a bump in salary, everything looked great — and I quit the next day,” he says with a  smile. 

“I was like ‘I’m gonna regret this forever if I don’t go back and do some music stuff.’ So I  started writing songs again, every day. I was obsessed. I still am.”  

Since that time, Green estimates he’s written at least 1,500 songs — some of which have been cut by country stars like HARDY & Florida Georgia Line. He’s also just finished his first tour with  Mitchell Tenpenny — a jaunt that spanned 30 stages and 15 states.

His plans for 2022?  

Releasing new music and most importantly, cultivating his relationship with his fans.  

“Most people sign a record deal with like 300,000 people following them. I signed with a  thousand friends on Facebook,” Drew says with a self-deprecating laugh. “Then COVID hit a  month later! Everything that could be the worst situation for a guy, I feel like I’m in that boat.  But I wouldn’t trade it for the world.” 

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