Kenny Chesney Opens Up About Grieving Loss Of Legend Brett James

By Kelly Fisher

November 13, 2025

Photo: Getty Images

Kenny Chesney vulnerably reflected on significant losses in his life during a conversation with Anderson Cooper on his CNN podcast, All There Is.

During the conversation, Chesney remembered late songwriting legend Brett James, who died in a small plane crash in North Carolina on September 18, along with wife Melody Carole, 59, and stepdaughter Meryl Wilson, 28. He was 57. James wrote or co-wrote some of the biggest hits in country music, including Chesney’s “Out Last Night,” “Reality” and more.

“I’ve lost someone recently, someone that I created with for a very long time. My friend, Brett James, who was killed in a plane crash a couple of months ago,” Chesney shared with Cooper. “And it's been hard because we were brothers and we were songwriting partners. And we came from different places. But I mean, he wrote so many of my songs and those that he didn't write with me, I wrote with him. His creative energy and his creative soul changed my life. There's a huge part of my show that is- that's our creative energy. And then all of a sudden that stops.”

Cooper asked the recently-inducted member of the Country Music Hall of Fame whether he feels a connection with James whenever he sings songs the two wrote together.

“So the first time I sang one of his songs after he passed was at Farm Aid with Willie Nelson in Minneapolis. And all of a sudden it hit me,” Chesney replied. “I was going to do a song called 'When the Sun Goes Down,' which he wrote by himself. And it was the first time it was really- the wound was really open. It was really fresh, his passing. And I had to go up there and sing that song. And I haven't had to sing it since. But I'm going to, because I'm not going to let that stop me. It's almost like in a celebratory way now […] Brett was just one of those guys that, I mean, I thought was always gonna be around. And it's been really, really, really difficult. And it was a moment that really hit the whole town of Nashville really hard. Because he just didn't create for me, I mean, he was a creative machine and a soul and a great- you know, a great guy and a dear friend […] I don't know, he was just a brother and it would just- he had a bad day in a plane, you know, and it sucks.”

Chesney was one of many artists in the country music community to remember James in a heartfelt tribute shortly after his passing, along with Carrie UnderwoodSara EvansDierks BentleyTim McGraw and many more. See the tributes here. Chesney said the loss is “a very difficult goodbye.”

“It’s hard to process his creative soul being gone. This kind of loss. I feel as if part of my creative soul went with him. It will be a void in my life and creativity forever. I’ve never known writing songs or being on the road without him,” Chesney shared at the time, in part. “I can’t believe I’m saying it but adios Brett James. Thank you for being a lifer, for being a shirtless, sunburned troubadour, for your friendship, your songs and all the laughs. Save me a seat at the After Party!”

Kenny Chesney
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