Dean Alexander arrived in Nashville in 2006 with $100, a car full of clothes and a dream. Those three ingredients make a fine country cliche, but don't try comparing his story to another singer's quite yet. That's literally all the West Virginia-raised singer had. As far as he was concerned, there was nothing to return home to.

“I remember laying there in bed and watching a roach that could have carried away any one of my dogs when I was growing up, just crawl right across my stomach," Alexander says, laughing as he describes his first 'home' in Nashville. "And I remember going ‘No! I’m not going back. I’m not going back. I’m not calling home to my grandparents.’ And I never did.”

Lord knows where I’d be if my parents were still alive,” he says. “Lord knows where I’d be if I would have decided to go back home to my grandparents. I don’t know, but I’m grateful for the tragedies in a weird way.

The roach moment actually came after things started to take a turn for the better. Alexander was a talented drifter those first few weeks -- a vagabond that learned to find the best bathrooms, sources of food and other life necessities.

“I remember I used to have to take showers in truck stops. I’d sleep in parking lots and the cops would knock on my windows at 4AM and tell me I had to go," he shares. "My lowest moment in Nashville was in the first week … having to walk into a dollar store and buy little pork and beans with a plastic spoon that I got from McDonalds, and open those suckers up and eat those in my car. Dude, that was the lowest moment.”

The night before calling ToC from his (presumably roach-free) home in Nashville, Alexander was in Pittsburgh playing a radio show for a local station. Long flights, late nights and egg burritos to kill what the night before created are as much a part of his life now as stability wasn't when he was 20 years old. An argument with his grandfather chased him away from home. So he made the seven-hour drive along I-64 to find his pot of gold in Music City.

Of course, that treasure only exists on television. Like most players who "make it," Alexander's journey was, and is, a grind. Day jobs and the occasional gig at night led to another bigger gig and better job. The years turned. He slowly began to climb the ladder. A quasi-residency at Layla's Bluegrass Inn provided stability he'll never forget. In fact, when asked where he wanted to shoot his debut music video, he didn't hesitate.

Dean Alexander
Michael Loccisano, Getty Images

“We had the option to go to the beach or all this other stuff but I wanted to go back to the place where it all started with me in Nashville,” Alexander says. “I literally learned how be an entertainer off of that stage.”

His biggest break was as unexpected as the tragedies that speckled the first 20 years of his life. Alexander was doing landscaping work and one day he found himself working for Barbara Orbison, Roy's wife and founder of Still Working Music. “I was working in her garden when she walked out and asked what I was here for,” he recalls on his Facebook page. “I knew exactly what she meant, so I went to my car right then and handed her a CD and she gave me my first publishing deal two weeks after that.”

Soon, he was a touring guitarist, then he was talking about his own record deal. The time before his life in Nashville was cursed, he says. Both parents were killed in car accidents. He was raised by his grandparents, but kicked out when his grandfather learned he'd snuck out to play at a local country bar. There was literally nothing to return to -- but returning to nothing actually turned his fortunes around.

Some time after getting settled, Alexander found work and called his grandfather to share the news. "When I called I found out he had brain cancer and he had six weeks to live," he says.

What happened next seems like a scene from a movie. He hustled to scrounge up extra money to get back to Parkersburg to see him, bringing a Gibson guitar with him, as his grandfather always wanted one. One night, at about 11PM, he walked into the room to find the man that raised him alert, but very fragile.

“When I got there, I sat down, and he wanted me to sing two songs to him," he says. "So I sang a couple of hymns. I asked him to forgive me and all that kind of stuff.”

“I left the hospital to go back to their place to sleep that night and before I could make it back to their house they called me and told me he’d just died," adds the singer.

When your life is truly like a movie, is it upsetting to be told so? Alexander's pondered this and admits he doesn't like it, but it's not insulting.

Last Question Dean Alexander

"It’s a beautiful tragedy," he says. "I kind of look at my life and I’ve always known I was destined to do something. I don’t know how big my star is gonna get, but I know I was put on this earth to tell a story.”

He adds poignantly, “I kind of know what to say when nobody else knows what to say."

With 'Live a Little' climbing the charts and an album full of revealing country rockers and ballads ready for radio after it, the Dwight Yoakam-inspired Alexander's fanbase is swelling. His big country voice is perhaps only overshadowed by his maturity. This singer seems like a man you can trust to stick around for five, 10 or 20 years.

“Lord knows where I’d be if my parents were still alive," he says, bringing some firsthand perspective to the events that got him here. "Lord knows where I’d be if I would have decided to go back home to my grandparents. I don’t know, but I’m grateful for the tragedies in a weird way.”

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