Kenny Chesney Honors ‘When the Sun Goes Down’ Writer Brett James: ‘His Loss Leaves a Lasting Void in My Life and Music’

In his final interview, recorded just a week before his passing, James shared a lighthearted story about Kenny Chesney.

Kenny Chesney is honoring the memory of his longtime collaborator and friend Brett James.

On Monday, Sept. 22, the country star shared a moving Instagram tribute following the news that James, 57, died in a plane crash on Sept. 18 in Franklin, N.C. His wife, Melody Carole, and her daughter Meryl Wilson were also on board and did not survive.

“I haven’t wanted to post because I didn’t want to believe it,” wrote Chesney, 57. “Brett and I shared something rare — a brotherhood, a deep kinship. We wrote Reality and Out Last Night in the same afternoon on my pool deck in the Virgin Islands just two days after Christmas.”

He reflected on their creative partnership with gratitude: “We had so much genuine fun writing songs together over the years, and I’m really going to miss it.”

For Chesney, the loss goes beyond music. “It’s hard to process that his creative soul is gone,” he continued. “I feel like part of my own went with him. There will always be a void in my life and in my creativity. I’ve never known what it’s like to write songs or tour without him. Half the songs in my shows are ones he wrote or that we wrote together. Moving forward, I won’t be able to play a show without thinking of him.”

He ended his tribute by thanking James “for being a lifer, for being a shirtless, sunburned troubadour, for your friendship, your songs, and all the laughs,” before signing off with: “Save me a seat at the After Party!🙏😎🧡🌴☀️💔” Chesney also shared lyrics from his 2020 track Knowing You, a song that now feels especially poignant.

James and Chesney’s creative relationship was long and fruitful. Their best-known collaboration is “When the Sun Goes Down,” the chart-topping title track from Chesney’s 2004 album featuring Uncle Kracker. James also penned fan favorites like Out Last Night and Keg in the Closet.

In what would be his final interview, recorded a week before the crash and released Sept. 24 on Now Hear This Entertainment, James spoke warmly about his bond with Chesney. “I’ve been blessed to have more than 40 songs recorded by Kenny Chesney,” he said. “He’s one of my dearest friends and one of my favorite artists on the planet.”

He recalled one of their most memorable writing sessions together — the same story Chesney alluded to in his Instagram post. “We had a bit of a reputation for cutting loose, and one night after Christmas was no different,” James said with a laugh. “The next morning, I grabbed my guitar and sat on his back deck with a cup of coffee, just taking in the most beautiful view I’d ever seen. Kenny stuck his head out the door and said, ‘We went out last night.’ Right there, we knew we had a song.”

That morning, the pair wrote Out Last Night, and later that day, Reality. “All we did was have fun,” James recalled. “There was no pressure to write a hit — just to enjoy each other’s company, make things up, and laugh. It was one of my favorite days of my life.”