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Legendary Songwriter Dean Dillon Talks Career with George Strait, Modern Country

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“I never wrote songs for George Strait,” says Dean Dillon, the hall of fame songwriter who penned more than 50 tunes for George Strait. “But I’ve been accused of it,” he chuckles.

Of course, what Dillon means is he never deliberately thought, “What would George sing?” But he wrote some of the most iconic songs Strait ever sang. In fact, the world’s introduction to Strait came by way of Dillon’s song “Unwound.”

That tune opened Strait’s debut album Strait Country, more than half of which came from Dillon’s pen. The album took off, and there was no turning back. Dean poured his heart out on the page, and George sang it to millions.

Of course, Dillon also wrote many other hits, including “Tennessee Whiskey” (originally pitched to Strait), for many other artists, including Kenny Chesney and Toby Keith.

And that’s precisely what makes Dean Dillon’s storybook career so compelling: “All that time I’m just writing Dean Dillon songs, man.”

An Unlikely Beginning

By his own account, Dillon and Strait met under pretty unlikely circumstances. The whole story is worth reading. Better yet, it’s worth watching — a new documentary all about Dillon’s life called Tennessee Whiskey: The Dean Dillon Story premieres in May. But here’s an abridged version.

In 1973, a teenaged Dillon moved to Nashville from tiny Lake City, Tenn. He had, as the cliche goes, nothing but a pep in his step and a song in his heart. To put it more starkly, he slept in a coal bin. “I’m not making this shit up,” he says. “For two weeks, until I got my legs under me, I slept in a coal bin.”

Dillon struck up a friendship with a fellow writer Frank Dycus, which led to years of songwriting together. One day, while sitting on a front porch on music row and writing — and drinking, as they often did — Blake Mevis swung by in his car and yelled out, “I got this new kid from Texas, y’all got any songs?”

Seriously, that’s how it started.

A Beautiful Friendship

The next three and a half decades saw Dillon riding a roller coaster existence, full of chart-topping successes, struggles as an artist, self-destroying addictions and personal redemptions. But Dillon’s relationship with Strait was a constant through it all.

The highs included 11 No. 1 singles with Strait and timeless songs like “The Chair,” “Marina Del Rey” and “Easy Come, Easy Go.” Despite two drastically different lifestyles at the time, Dillon and Strait always had a beautiful friendship, both professionally and personally.

“We had this unwritten rule that everything I wrote that I believed in, I would give to him,” Dillon says. “And I knew he’d sing it exactly how I gave it to him. I didn’t want anybody less than the best singing these songs, and to me George Strait is still the best country singer out there.”

“EASY COME EASY GO, EMBED”

In fact, much of what Dillon does nowadays — selling out theaters across the country a few nights a week — replicates how he’d go through songs with Strait. “I always loved the element of just me and a guitar sitting down, singing songs,” Dillon says. “That’s what made me a living and what I’d do with George.”

Eventually, Strait and Dillon went one step further, writing together. Dillon says he never doubted the pair could do that either, given Strait’s career-defining ability to pick good songs. “When he first started his songs weren’t great, and he’d tell you that, but if he hadn’t had the career he has as a singer, he’d be a chart-topping songwriter,” Dillon says. “Oh yeah, he’d be there.”

The Kids Are… Alright

So now that Strait is mostly retired, what does Dean Dillon think of music nowadays? Well for starters, he’s still a huge part of the industry. Dillon has recent cuts with all kinds of artists, from Mo Pitney (one of his current favorites) and Randy Rogers Band to Blake Shelton and Garth Brooks. But something is missing.

“You gotta understand, I live, eat, sleep and breathe songs,” Dillon says. “Where are all the great songs that I know get written in Nashville?” Needless to say, the bro country phase did not sit well with him.

On the one hand, he gets it. Paraphrasing Toby Keith, he says, “We were the circus once. And now it’s their turn and it’s all good and well.” But on the other, he’s not hearing the seriousness of music. Or the variety.

“Every song is about the same damn thing,” he says. “Daisy Dukes, trucks, beer, lake banks, time, after time, after time, after time. The bro country thing started 12 years ago, and 12 years later, they’re still singing the same things. Do they not evolve? Get older? Get married? Have kids? Get jobs and shift in society? There’s no movement in it.”

READ MORE: The Most Beloved George Strait Lyrics of All Time

But, at the same time, he believes the up-and-coming generation is smarter than the last. And that includes his daughter Jessie Jo Dillon. “She’s got it way more together than I did at that age,” he laughs. “Peanut can write her brains out.”

So don’t get it wrong — Dillon isn’t begrudging anybody else’s success, because Lord knows he has plenty of his own. But he’s refreshingly honest, pensive and gracious about the role songwriting plays in his life. He’s seen songs move and touch people profoundly. The whole thing is still kind of magical, honestly.

“The amazing part of Nashville writing is what it’s always been,” he says. “You can sit down in a room with somebody you’ve never met and know nothing about, and three or four hours later you write this great song. How we do it, I don’t know, but it happens every day.”

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Legendary Songwriter Dean Dillon Talks Career with George Strait, Modern Country