Kenny Chesney made an appearance at Country Radio Seminar in Nashville on Tuesday (March 14), offering insights into the key decisions that shifted his career into overdrive — propelling Chesney from a struggling singer-songwriter to a four-time CMA entertainer of the year winner, and one of country music’s most successful touring acts ever.
During a session moderated by Country Countdown USA’s Lon Helton, Chesney detailed the competitive mentality — influenced in part by his love of sports — that has led him to earn 32 No. 1 Billboard Country Airplay hits and 11 CMA Awards wins. Chesney played to over 1.3 million fans on his 2022 Here and Now Tour, and is slated to begin his I Go Back 2023 tour later this month.
“The one thing that I think that’s helped me … sustain any kind of success is the idea that you either get better or you get worse,” he said, sharing advice he received from big-wave surfer Laird Hamilton. “He said, ‘You get 1% better or worse every day…’ I’ve tried to get 1% better as a writer, a person, a producer. That’s the mentality I’ve had over the years.”
Tennessee native Chesney also discussed his early career years, when he first signed with the country division of Capricorn Records and issued his debut album, 1994’s In My Wildest Dreams. Sony Music executive Joe Galante heard Chesney’s music and soon signed him to Sony’s BNA Records imprint, where Chesney released his sophomore project, All I Need to Know, a year later.
“Joe had never seen me perform, never saw me live,” Chesney said. “And thank God … I wasn’t comfortable in my skin as an artist then. And Joe signed me off of that [record].”
During the discussion, Chesney also recalled his disagreement with Galante over releasing “Don’t Blink” as a radio single. The song would be come a four-week Country Airplay No. 1 hit in 2007.
“When we released that song, Joe [Galante] and [former Sony Music A&R executive] Renee Bell really wanted that song released, and I hated it,” Chesney said. “I felt like it just touched every button you could possibly touch to get somebody to like a song and I hated it. We were at ABC Radio Networks in Dallas, and we were on the plane there, and I was in Joe’s ear the who two-hour ride about how much I hated this single choice: ‘It’s never gonna work, this is going to be the end of everything. I’ve worked really hard to be here and you’re gonna cut my legs off with ‘Don’t Blink.’’ I did my interviews and we are coming down the escalators and the lady at the front desk tells me, ‘I just love “Don’t Blink”!’ I looked at Galante and said, ‘You told her to say that.'” (“Don’t Blink” ended up being a four-week No. 1 on Country Airplay.)
Chesney noted that early in his career, even though he was notching hits, he had yet to set himself apart as a unique artist. “I was a lot like a lot of artists, honestly,” he recalled. “I was trying to be the newer version of George Strait. I think Garth [Brooks] would tell you the same thing, he loved George. That was the bar. I wore a belt buckle. I was trying to be that.”
By the time he released a Greatest Hits album in 2000, he had earned several top 5 hits and No. 1 hits. But he needed to make some key changes to stand out from the crowd. “Everybody knew the songs, but they didn’t know me,” Chesney said. “I had 16 songs in a Greatest Hits package, and then I would go play a fair or whatever and people would go, ‘Oh, that’s the guy that sings that song. Oh, he sings that, too.’ So they hadn’t really connected yet. But the moment I stopped trying to be George Strait, that was the moment my life changed. I started really writing songs. And my life in the Virgin Islands, I spent a lot of time writing out there.
Helton noted that from 1993, Chesney released a new album nearly every year, until a two-year gap between 1997’s I Will Stand and 1999’s Everywhere We Go, and a three-year gap to 2002’s No Shoes, No Shirt, No Problems — with a cover conveying some of the beach lifestyle, “Island Kenny” branding fans would come to associate with Chesney.
“At one point you told me you were watching CMT and you saw video after video of male singers — hat, belt buckle — and you knew something had to change,” Helton noted.
“This isn’t a slam toward anybody, but I realized there were acts out there that felt the same way I did,” Chesney recalled. “We were all trying to reach for Strait. I didn’t have as good of a song as Tracy Lawrence had, with ‘Time Marches On.’ I just felt I wasn’t truly being authentic as an artist during that time. There was a phase, after Garth hit, where everybody wore the same shirt.”
Chesney said spending time in the U.S. Virgin Islands, where he filmed music videos for songs including “How Forever Feels” and “I Lost It,” provided creative inspiration.
“I found myself writing songs about the characters and the people I met, their stories. As much of a marketing ploy as it looks like, it really wasn’t. It was just a huge part of my life.”
Chesney also discussed the balance of making music and also keeping his personal life private, in the era of artists documenting their lives 24/7 on social media.
“I just don’t feel comfortable going down that road,” Chesney said. “I work really hard to be this person, and I want to keep some sort of dignity and integrity intact, and not feel like I’m selling my soul to get higher in the consumption chart. I realize that, the person I am today, some things are fair game. One of the reasons I’m so private is when my life started to change and people started caring at a different level, the only thing I could keep to myself was the intimate details of my life. Now everything else is fair game. Can people talk about you? They make stuff up, they run with it, the media runs with it. People are really curious to know those intimate details, I get that. But the reason I’m so private is that if I don’t keep those details to myself, where do I go? What else do I have?”
Helton asked if the media attention surrounding Chesney’s marriage and subsequent annulment to actress to Renee Zellweger in 2005 heightened his sense of privacy.
“That changed a lot,” Chesney said. “What is interesting is we were playing stadiums already, and after that … I didn’t have social anxiety before that, [but] then you add our success and then you add that to your life and you have a little bit of social anxiety. And now, dealing with the way the world is today and how social everything is, and how information is transferred — yeah, you’d have to be crazy to want to be a celebrity today.”
Asked whether he enjoys being a celebrity, Chesney replied, “Not really. I enjoy certain things about it … I shy away from the celebrity thing. I say no to a lot of things that come my way that a lot of people might say yes to — it’s too celebrity-oriented in nature. I would rather be creating.”
Chesney signed with Warner Music Nashville in 2018, and is currently creating his next album for the label, noting that he’s nearly halfway done with the project.
“The next record is important — they are all important,” Chesney said. “No matter who you are or where you’re at in your career arc, every album is important. You want somebody to do something, you want somebody to be happy, you want somebody to chase their own dreams because of your music.”
Asked if he already has a first single prepared from the project, Chesney said, “Well, I could, but I’m trying to beat it.”
As Chesney nears his milestone 55th birthday on March 26, Helton asked how long he plans to keep touring at this level.
“I feel great and I still have the fire to go out there and give people every single thing I have,” Chesney responded. “Yes, as long as I can be creative and do what I do at the level that I do it.”