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Caitlin Cannon on Her Dolly Parton License Plate and Transcendental Rehearsal Space Moments

Tuesday, May 06, 2025 By Mayer Danzig

Caitlin Cannon (credit Stacie Huckeba)

Photo credit: Stacie Huckeba

Tell us about your tour vehicle.

I drive a 2013 Toyota Rav 4 with a Dolly Parton License plate. It had 40K miles on it when I bought it a few years ago, now it has 190k. I think we can get around the sun a few more times.

How do you eat cheaply and/or healthy while on tour?

Ha, intermittent fasting?! Chipotle is great for healthier options on the road, Chik-fil-A is the guilty pleasure, and Starbucks is the emotional staple. I have the app, and it helps justify the lattes when the points add up.

How many strings do you break in a typical year? How much does it cost to replace them?

I’d say I break more nails, when they get stuck in the strings. And as far as replacement, it’ll grow back for free, but a basic manicure runs about $50.

Where do you rehearse?

Generally we have rehearsals at Misa’s (my producer) in the same room we recorded the record in. The craziest experiences are the transcendental kind, getting to hear how the songs come alive when we play as a band and getting lost in all that.

What was the title and a sample lyric from the first song that you wrote?

Ummm the first, first, first song I wrote when I was 18 and it was called “The White Horse Song” and the lyrics were: “You fucking bastard, you fucking bastard, I hope you die.” Can’t for the life of me remember what I was so angry about. Guess I got over it. I still use songwriting as an alternative to killing people.

Side note- I have a weekly livestream called ‘Married to Monday’ in which I play something new, old, borrowed and blue. But I reserve the right to switch up the order in case anyone requests something ‘old’ that is very, very bad like that.

Describe your first gig.

My first official gig was about 10 years later at Kay B’s house concert in lower Manhattan, where I opened for David Olney. He was so kind to me and treated me as if I were a pro. He was a real pro like that.

What was your last day job? What was your favorite day job?

I had a salon in Colorado prior to touring full time. I like making haircuts, but it definitely wasn’t my favorite. If I were going to have another non-music job I’d want it to be icing cupcakes or raking sand on a tropical island.

How has your music-related income changed over the past 5-10 years? What do you expect it to look like 5-10 years from now?

Music-related income, I like how you put that. It’s funny because you don’t really know where it’s going to come from. It’s a job that requires much faith. Much faith that the IRS is too busy for you. I might see $100 a month from streaming (on a good month)! And bands have to be paid, so it is hard work. You get creative, offering music related services and merch. I also work for a custom songwriting company called Songfinch. But yeah, it a lot of just don’t quit and hope for the best!

What one thing do you know now that you had wished you knew when you started your career in music?

I had to learn the lesson, but I wish I knew that trying to be normal wasn’t going to pan out and stayed the course in my 20’s. I would also tell myself not to force anything. That I’ll tap into something pure the less I push. The quality of my music really changed once I began trusting that. I’m still working on implementing it into the rest of my life.

Caitlin Cannon is a Nashville-based singer-songwriter originally from Colorado. She began her career in musical theater before turning to songwriting, eventually releasing her debut solo album The TrashCannon Album in 2020. In 2021, she partnered with fellow artist Alice Wallace to form the duo Side Pony, releasing their debut album Lucky Break later that year.

Beyond music, Cannon is a force of creative energy. From her comedic debut on Kill Tony to teaching songwriting to inmates through her Beyond Bars program, she defies easy categorization. Beyond Bars, developed in collaboration with The Cultural Arts Alliance and The 30A Songwriters Festival, will be featured on Meg Ryan’s series Empowered this spring, highlighting her commitment to bridging art and social impact.

Love Addict, her latest album, will be released on May 9th. Connect with Cannon online and on the road.

Filed Under: Americana, Interviews, Singer/Songwriter, Why It Matters Tagged With: Caitlin Cannon

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