Brett James, Billy Montana and Tom Douglas Sing Their Hits at Songwriters Under the Stars

Music City Hit-Makers returned to Cheekwood this past weekend with their Songwriters Under the Stars event, which combined three of Nashville’s esteemed songwriters with the Music City Symphony. On a stage set up outside of Cheekwood’s picturesque Swan Lawn in Belle Meade, Brett James, Billy Montana and Tom Douglas were backed by a 17-piece orchestra led by music director and arranger Charles Judge for two nightly concerts on Oct. 12 and 13.

The three songwriters have a combined 50 No. 1 hits, and ahead of each performance they often told the stories behind their songs. The event, which was scheduled for 7:30 p.m. on Saturday, was pushed up 30 minutes due to the forecast. The impending threat of rain didn’t damper spirits though, as the botanical garden’s property was filled with concertgoers bundled up and seated on blankets and lawn chairs. Performing a 40-minute set before the symphony retreated indoors following rain, each songwriter expressed his gratitude to be part of the event.

“It’s a joy to be with you and hear our songs re-imagined with this amazing orchestra,” Douglas said. “When we rehearsed for the first time Wednesday night . . . it’s truly overwhelming. I had to catch myself from falling into a pool of tears.”

Douglas’ emotion-fueled songs likely had his audience in tears as well. On Chris Janson’s “Drunk Girl,” the heartfelt piano ballad was transformed with a striking string arrangement that made the already powerful lyrics even more poignant. Ahead of his performance, Douglas explained that the idea for the song came from a line he had written for his son’s commencement address in 2013.

“One of the lines in the speech was, ‘Gentleman, there’s going to be sometime during your freshman year where a young lady is going to be over served and the gentlemanly thing to do is take the drunk girl home.’ It was very poignant at that moment and had some resonance,” he shared.

Four years later, while he and his son were at the Nashville jail for a songwriting class with inmates he was instructing, the sheriff brought up those exact words from his speech years prior.

“The sheriff said to my son, ‘Tommy, do you remember four years ago when your dad gave the speech and he had that line in there about take the drunk girl home?’ The sheriff then pointed with a wide sweep and he said, ‘There are so many men in this institution who wouldn’t be here if maybe they heard that admonition somewhere in their life,'” he recalled.

Struck by the sheriff’s conversation, later that day Douglas brought the song idea to his co-writers Janson and Travis Hill, and they wrote what would become the singer’s latest single, “Drunk Girl.”

Montana, meanwhile, shared another touching story about his previous No. 1 with Lee Brice, “Hard To Love.” The singer had the opportunity to go overseas to play for our troops and while performing the song in Afghanistan, a soldier called his wife to tell her that the man who wrote their song was singing it to him. Backed by a stunning string arrangement, the love song came to life in the outdoor setting.

Additional highlights included James’ standout re-interpretation of Dierks Bentley’s “I Hold On.” A song that Bentley came to him with the idea for, on “I Hold On” James’ soulful vocals soared alongside the Music City Symphony. While the symphony’s involvement was cut short due to steady rainfall several songs in, Douglas, James and Montana stuck around to play a few more songs with their acoustic guitars. Backed by piano, bass and drums, the evening took a turn as more of a guitar-pull but was no less inspiring.

As the rain poured down, James fittingly performed Carrie Underwood’s “Something In the Water” while Montana played Sara Evans’ “Suds In the Bucket.” Douglas continued to tug on the heartstrings of those in attendance with Miranda Lambert’s reflective tune “The House That Built Me” before James closed the evening with the feel-good Kenny Chesney and Uncle Kracker collaboration “When the Sun Goes Down,” which he told the crowd he penned in 20 minutes on the way home from a co-write. The track had the audience dancing and singing along in the rain and as the performance came to a close, it was evident that no amount of rainfall could put a damper on the spirit of those attending Songwriters Under the Stars.