Dean Dillon Reflects on His Career and the Evolution of Country Songwriting
As one of country music’s most successful songwriters behind more than 70 George Strait songs and others recorded by the likes of Toby Keith, Kenny Chesney and more, Dean Dillon has seen it all in the music industry.
The renowned songwriter performed at the 26th Annual Key West Songwriters Festival in early May, and he chatted with Taste of Country about his storied career, the importance of highlighting songwriters and the evolution of the country music industry. And when looking back on his legendary career so far, Dillon couldn’t help but highlight the man who helped him in his early days: Hank Cochran.
"I got lucky, man. I got to write with the best when I was a young guy," Dillon shared prior to his acoustic round with Scotty Emerick at the historic San Carlos Institute in Key West, Fla. "Hank Cochran was my mentor. It’s hard to beat 'Make the World Go Away' as your mentor. He thought me pretty much everything I knew about writing great songs. I could write before, but I never wrote the caliber of song that I wrote thereafter, after Hank."
That early education with Cochran led Dillon to writing legendary songs that have touched multiple generations. From David Allan Coe’s "Tennessee Whiskey," to George Strait’s "Ocean Front Property," to Toby Keith’s "A Little Too Late," there seems to be a Dillon song for every country fan. While all the songs he’s penned are no doubt special to him, two songs, in particular, stand out to him.
"Kenny Chesney’s song 'A lot of Things Different.' I love that. I wrote that with Bill Anderson," says Dillon. "And then [George Strait’s] 'The Chair.' I love 'The Chair,' I always have, and George sang the fire out of it. Just always been special to me."
After writing thousands of songs throughout his career and amassing major accomplishments, including being inducted into the Country Music Hall of Fame in 2021, Dillon admits he has “slowed way, way down” on the songwriting front. The Tennessee native is busy watching his daughter, songwriter Jessie Jo Dillon, make her mark on the country world, and he produces other artists, including country trio Due West. Dillon has also taken stock of the state of the country music format today, commenting that the process of songwriting has changed dramatically from when he began his career.
"It’s more radio-oriented," he says. "I hate to say it, but more one-hit wonder-ish kind of thing now, as opposed to back then when we strived to write great every time. I don’t think that holds true now. I think what holds true is radio candy, I call it. You can call it whatever you want to. I don’t begrudge that one darn bit. A lot of these young kids are having great success with it, and that’s wonderful."
"Like I said, I don’t begrudge it one bit, but for this old cowboy, I’m not going to do anything different than I’ve always done: sit down and try to write the best damn thing I can write that day," he adds.
Although the music industry keeps evolving and changing, Dillon is a fan of many young singers, including Luke Combs (Dillon is a co-writer on Combs’ new song, “Tomorrow Me”), and Lainey Wilson, who is performing at Dillon’s Legends of Music Row Festival taking place in Key West Oct. 13-15. And, as someone who has a wealth of experience in the music business, he has plenty of wisdom to share with young artists.
"It’s a different game, but my advice to the young ones is, be true to yourself, man, and if you want to write great songs and nothing but great songs, write great songs and nothing but great songs," he says. "Don’t settle for second best. No second-best lines, none of that. Go for it. Find your voice. Find yourself."