Brett James Talks ‘Greatest Songwriting Day’ With Kenny Chesney on Behind the Setlist Podcast

Brett James has spent countless days co-writing with a who’s who of Nashville musicians and songwriters, crafting songs that would be recorded by the likes of Carrie Underwood, Jason Aldean and Dierks Bentley. One day stands out as perhaps his most fruitful songwriting session: writing with Kenny Chesney at the country star’s house on the island of St. John in the U.S. Virgin Islands.

Two days after getting a call from Chesney, James was with the country singer on St. John on a December evening. “We smelled that salt there and felt the warm breeze and went out and had some fun that particular night,” the Nashville-based songwriter recalls for Billboard‘s Behind the Setlist podcast.

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“The next morning, I wake up and I grabbed a cup of coffee and my guitar and went out sat on his back deck, which had one of the most beautiful views I’ve ever seen in my life,” James continues. “And I just sat there kind of strumming a guitar, drinking coffee and thinking about life. And two or three hours later, finally, the back door to his room kind of creaks open and Kenny sticks his head out. He looks at me and he goes, ‘Brett, we went out last night.’ And I was like, ‘Well, yeah, we did. And, you know, maybe that’s the song we ought to write today.’ So I started singing and strumming a little groove and singing a little song and our single melody and he kind of joined right in and you know, we just like all good song, we just talked and laughed about the night before for a couple two or three hours and and we came up with the song ‘Out Last Night.’”

“Out Last Night” ended up being the first single on Chesney’s 2009 Greatest Hits II album. The trip would have been deemed a success based only on the first song, but James and Chesney pulled off the unlikeliest of encores by writing “Reality,” which Chesney would record for his 2011 album, Hemingway’s Whiskey.

“Both those songs ended up being No. 1 [on Billboard’s Hot Country Songs chart]” says James, who was inducted into the Nashville Songwriters Hall of Fame in 2021. “That was maybe the greatest songwriting day I’ve ever had, because that’s never gonna happen again. So I have to thank Kenny for that day. It was fantastic.”

Initially signed to Arista Nashville imprint Career Records, James released his debut solo album in 1995 but has since made a name for himself as a songwriter with hits such as Underwood’s “Jesus, Take the Wheel,” Bentley’s “I Hold On” and Tim McGraw’s “It’s a Business Doing Pleasure With You.” He released a solo album, True Believer, in 2020.

Listen to James’ entire conversation with the Behind the Setlist podcast at Spotify, Apple Podcasts, Stitcher, iHeart, Amazon Music, Audible or Google Podcasts.

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