After releasing his self-titled debut album in 1995, Brett James pivoted to primarily songwriting, penning chart-topping hits for Carrie Underwood (“Jesus Take the Wheel” and Kenny Chesney (“When the Sun Goes Down.”) In September 2025, the prolific Nashville singer-songwriter died in a single-engine plane crash alongside his wife and stepdaughter in North Carolina. During a recent sit-down with CNN’s Anderson Cooper, Chesney reflected on the first time he performed “When the Sun Goes Down” after learning of James’ passing.
Videos by American Songwriter
Just two days after Brett James’ death on Sept. 18, Kenny Chesney took the stage at Minneapolis’ Huntington Bank Stadium for the Farm Aid 40 festival. That’s when, according to the newly inducted Country Music Hall of Famer, the gravity of his loss first began to set in.
“All of a sudden it hit me,” Chesney recalled. “I was going to do a song called ‘When the Sun Goes Down,’ which he wrote by himself, and… 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 he made it through, and says his next performance of “When the Sun Goes Down” will take on a much more joyous tone. “It’s almost like in a celebratory way now,” said Chesney, 57.
[RELATED: 4 of Brett James’ Most Influential Hits as a Songwriter That We All Know and Love]
Kenny Chesney Remembers Brett James’ “Creative Soul”
Expanding on the loss of his friend Brett James, Kenny Chesney said, “Brett was just one of those guys that. I thought was always gonna be around. And it’s been really, really difficult… I mean, he was a creative machine and a soul and a great guy and a dear friend, and we went on a lot of riding trips together and we had a ton of authentic live fun.”
“I don’t know, he was just a brother,” continued the “No Shoes, No Shirt, No Problems” hitmaker. “And… he had a bad day in a plane, you know? And it sucks.”
According to a report from the National Transportation Safety Board, James, 57, was piloting his Cirrus SR22T on a flight from Nashville’s John C. Tune Airport. He was preparing to land at to Macon County Airport in Franklin, North Carolina, when the plane entered a tightening spiral and crashed.
Featured image by Rick Diamond/Getty Images for BMI
Leave a Reply
Only members can comment. Become a member. Already a member? Log in.