Shortly after Caitlin Cannon took third place honors at this year’s Telluride Bluegrass festival, Saving Country Music published these prophetic words, “She’s not a songwriter for the winners. She’s a songwriter for the broken, the downtrodden, the losers, the motherf—. She sings about real sh— that most other songwriters don’t have the guts to broach. A crack pool player and a hilarious person on stage that could have a second career as a comedian, Caitlin Cannon is one of those country artists that slides so criminally under the radar, it angers the blood…” 

While Cannon has done her share of winning (Songwriter Serenade 1st Place 2023) her ambitions do seem to reflect the above review. Inspired by the 33 year-to-date incarceration of her brother, she created a songwriting program in partnership with the Cultural Arts Alliance of Walton County (30A) that holds a residency for her at Walton Correctional Institute where she teaches inmates to write songs.