Caitlin Cannon’s songwriting walks a razor’s edge between humor and heartbreak, satire and sincerity. She disarms listeners before pulling them into raw explorations of love, loss, addiction and beyond. Think ‘Cosmicana’—a sound as expansive as the storytelling on her 2025 LP Love Addict, produced by Misa Arriaga (Kacey Musgraves, Willie Nelson), where dreamy Americana meets with classic country. The genre bend tracks, given Cannon’s influences—from early ’90s country icon Pam Tillis, who makes a cameo in the Love Addict music video, to Lucinda Williams, who has publicly praised Cannon’s work.
Beyond music, Cannon is a force of creative mischief. From her comedic debut on Kill Tony to teaching songwriting to inmates through Beyond Bars—a collaboration with the Cultural Arts Alliance of Walton County and the 30A Songwriters Festival—she defies easy categorization. Her socially resonant songs have earned top honors across national songwriting competitions and widespread critical acclaim. Still, Cannon’s live shows remain as funny as they are fearless—a balance critics have noticed. Saving Country Music calls her “a hilarious person on stage who could have a second career as a comedian… one of those country artists that slides so criminally under the radar; it angers the blood.”
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Honors / Awards
Folk Alliance - Official Showcasing Artist 2026 SCM’s Song of the Year Honorable Mention 2024 Americanafest - Official Showcasing Artist 2024 Songwriter Serenade 1st Place 2023 Telluride Troubadour 3rd Place 2023 American Songwriter Finalist 2022 The TrashCannon Album 9.5/10 - SCM 2020
BEYOND BARS:
Co-Founder, creator and lead instructor of Beyond Bars: A Prison Songwriting Program with The Cultural Arts Alliance of Walton County. —Featured on ‘Empowered’ with Meg Ryan
NOTABLE VENUES / FESTIVALS: Nashville: Skinny Dennis, Eastside Bowl, 3rd & Lindsley, The 5 Spot, The Basement, The Listening Room, City Winery (Nashville, Boston). Texas: Cafe Momentum, The Saxon, the Continental Club. California: Campus Jax, The Durango Songwriter's Film and TV Expo - Official MC. New York: Jalopy Theatre, The Knitting Factory, The 11th Street Bar, Rockwood Music Hall. Colorado: Ft. Lewis Concert Hall, Concerts in the Park, The Soiled Dove. Festivals: Stagecoach, Nikki Lane's Horseshoe Stage, Hudson Folk West Fest, Four Corners Folks Festival, Outlaw Snowdown, Mile of Music, The 30A Songwriters Festival and more.
Warmed / Shared Stages: The Reverend Horton Heat, David Olney, Lilly Hiatt, Kristina Murray, Flamy Grant, Eileen Jewel, Lydia Loveless, Sundance Head, Whitey Morgan, Phoebe Hunt, Dave Borne, Janiva Magness, Bonnie Whitmore, Graham Weber, Cowboy Candy
Press
“She’s not a songwriter for the winners; she's a songwriter for the broken, the downtrodden, the losers, the motherfuckers. She sings about real shit that most other songwriters don't have the guts to broach. A crack pool player and a hilarious person on stage who 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.” — SAVING COUNTRY MUSIC
“It’s hard to imagine another country album as effortlessly cool as Caitlin Cannon’s Love Addict.” — THE NASHVILLE SCENE
“Forthright as they are, Cannon says that digging [is] easier than skirting the issues, or making up fictional stories…” — BILLBOARD
“Up there with songwriters like Kacey Musgraves and Megan Moroney, with her tongue-in-cheek playfulness and her softened edged classic country sound.” — HOLLER
“Is anyone better at writing from the POV of the seedy underbelly with such empathy and respect for the people they see around them? …Hers is a singular and essential perspective.” — COUNTRY UNIVERSE
"Cannon is a sassy country music rebel known for her edge and wit, but this Americana tune has a melancholy Elliott-Smith-esque undertone to it" — RIFF Magazine
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“THAT WAS ACTUALLY PRETTY COOL”
—TONY HINCHCLIFF