“I Thought, ‘Wow, This Might Be Over For a While’”: Kenny Chesney on What Caused Him to Cry On-Stage, and How He Overcame It

Kenny Chesney has always been synonymous with the bright, joyful and carefree sound of tropically-tinged anthems such as ‘No Shoes, No Shirt, No Problems’, ‘Happy Does’, ‘Get Along’, ‘Summertime’, ‘Save It for a Rainy Day’ and ‘Beer in Mexico’.

But long-time fans of the five-time CMA and ACM Entertainer of the Year know that it's not always been sunshine and rainbows, with Chesney having to overcome a range of challenges and tough moments throughout his storied musical career.

But these low-points do not taint the sunny disposition and joie de vivre that permeates his music - quite the contrary, they accentuate it and give it newfound meaning. Light is so much more intense and brilliant when it shines in the dark.

In a new interview with Walter Isaacson for Amanpour & Company, while discussing his new book, HEART*LIFE*MUSIC, Chesney reflects on the emotional difficulties and turmoil that led to him crying on-stage in Indianapolis during a 2009 show.

“I had just been going nonstop since 1993”, the ‘Just To Say We Did’ singer-songwriter recalls, “And my life during that period, from 1993 to 2009...There was a lot that had happened in my life. There was a lot of change in my life. There was a lot of loss in my life. There was a lot of just me coming to terms with being this person”.

Chesney goes on, “All of a sudden, earlier that year in 2009, I started to feel numb. Numb to music, numb to life, numb to my friends, numb...just numb. And I didn't feel great. I didn't feel bad. I just felt in the middle, this middle-grey...and that's no way to make music, and it's no way to have a connection with an audience”.

The Knoxville native reflects on how that final show of the tour ended up being the breaking-point, “That last weekend, I was in Indianapolis, playing the Indianapolis Colts [Lucas Oil] football stadium, and I went into [‘Better as a Memory’], and it just hit me. I thought, ‘Wow, this might be over for a while’. I didn't know if it was going to be two months or two years - or 20. I had no idea, but I knew I couldn't go on feeling like that. And it just hit me...The dam broke inside of me”.

Thankfully, Chesney eventually emerged from the depths of this heavy apathy, with the ‘Everything's Gonna Be Alright’ hitmaker outlining how another project helped to reignite his creative spark, “I pulled out of it. I didn't that night. You know, luckily, that was the last song of the show. But I took all of 2010 off, and then I started making a film for ESPN called Boys of Fall. And all of a sudden, I was in the living rooms, and I was the interviewer. I was interviewing Bobby Bowden, Nick Saban, Bill Parcells and John Madden - all these people that meant so much to the sports world, and to me and my father, because we watched a lot of football. All of a sudden, I felt it back. I felt, ‘Oh, this is inspiring me in ways that nothing else could at the moment’...I felt this creative energy. It was a Godsend, and I needed it so bad. After that, I felt creative again. I felt happier, I felt lighter. I was a better son, I was a better friend - and I was a better songwriter”.

Although he remains most recognisable for his playful beachside earworms, all of Chesney's albums portray a willingness to balance this light-hearted, island-inspired lustre with more melancholic hues. Chesney tackles grief with level of sensitivity and intricacy few others can match on ‘Wherever You Are Tonight’, ‘Sing ‘Em Good My Friend’, ‘Guys Named Captain’ and ‘Happy on the Hey Now (A Song for Kristi)’.

As Chesney explained to Holler during his 2024 conversation ahead of releasing BORN, “The truth is: that's everything life is, right? We all have trials, tough stuff, lose friends. We all have wins, great moments, crazy adventures. I think the reality is to feel all of it, to appreciate everything and to meet every experience where it is”.

He then touched on the secret sauce behind his process, “Some people might think my records have a split personality, but really, it's about how life actually is. The secret - and ‘Guys Named Captain’ is all about that - is to understand that no matter the low moments, look for the sunshine. Because that sunshine will pull you through”.

It's undoubtedly sage advice, and without the valleys he had to trudge through - such as that fateful 2009 on-stage breakdown - who knows if Chesney's glass-half-full outlook would be the same today. Either way, we're glad to have such a force for light and positivity in today's country music landscape, with the ‘I Go Back’ crooner remaining one of the genre's most influential figures of the 21st century.

Watch Kenny Chesney's full interview with Walter Isaacson for Amanpour & Company below:

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