Born to songwriter Dean Dillon and Kenni Wehrman (A&R at Warner), Jessie Jo Dillon was not sure she wanted to get into the music business and spent time in Los Angeles contemplating journalism before returning to her Nashville roots. Now a well-respected and sought-after songwriter, Dillon is stacking awards and writing for artists including George Strait, Post Malone, HARDY, Miranda Lambert, Luke Bryan, Tim McGraw, Nate Smith, Brothers Osborne, Darius Rucker, Morgan Wallen, Jelly Roll, and many more.
Every collaboration is different. “Working with Jelly Roll doing a camp, he wants to hear a lot, then lives with it [before making] song choices,” shares Dillon. “Megan [Moroney] is opposite. She’ll have an idea, we’ll sit down [and] work.” For Dillon, it’s all about the lyrics. “I wanna know the theme. If I don’t like the lyrics, I don’t like the song. Nine times out of 10, that’s a jumping off point for me.”
Music is her safe place. “I always loved music. My childhood was pretty chaotic and music was a retreat. I was always writing stories.” Navigating Los Angeles for a year after high school to find herself, Dillon tried to talk herself out of it, but ultimately began songwriting, befriending Kathleen Carey at Sony (a friend and mentor to this day). On Carey’s encouragement, Dillon returned to Nashville at 19 and met Clay Bradley, who landed her a publishing deal. Finally confessing it all to her father, the two began writing together. “One of my first big songs, the first I cut, was with my dad,” says Dillon [George Strait’s “The Breath You Take,” won 2011’s Best Country Song GRAMMY].
“I look back [realizing I] wasted a lot of time not getting help,” admits Dillon. “I’ll watch other people and think it’s great their parent [helps], but I was so against it.” She even contemplated hiding her surname. Co-writer Shane McAnally admitted halfway through an early session that he didn’t want to like her because of her lineage, but thought she was awesome and asked her to work with him and Brandy Clark. Dillon says the two now feel like her siblings.
As Founder/President of Gatsby Records (under MCA), Dillon looks for artists with work ethic. “In L.A., Nashville, New York, Miami, throw a rock and you’re hitting someone talented,” says Dillon. “But the hard-working part, I don’t know if you can teach that—it’s either in them, or not.” Raised to work hard, she says, “every time I sit down, I’m striving for greatness and connection. I’ve not lost that. I hope I never do.”
Tell the truth and stay weird. Mentor Frank Liddell accepted an award saying, “tell the truth, it’s more interesting,” and co-writer Shane McAnally encouraged Dillon to, “step into your weird because that’s what makes you, you.”Co-writes also require surrender. “I want to tell their story,” emphasizes Dillon. “To help somebody find their own voice and brand feels really special. I love artists, I love records. Everyone wants to talk about an algorithm [or] numbers. I get it, but don’t give a shit. The same three people don’t need to have written every song on the radio.”
Dillon says lyrics usually give A.I. away. “We will have no A.I. on Gatsby. I get pissed at writers—everybody wants to use Suno. You’re making it smarter. It’s lazy. The day I start wanting to be lazy about my art is the day I need to do something else. We all need to look to the future, but there’s a beauty in the past you can bring with you. You don’t have to be chained to it, but I can’t lose my morals about art.”
Penning over 900 songs over 15 years, Dillon’s accolades include ACM, AIMP Nashville, Billboard’s Rising and MusicRow’s Female Songwriter of the Year, placement on Variety’s List of Power Women, CMA’s Triple Play Award, and a GRAMMY Songwriter of the Year nomination next month. Upcoming projects include Tucker Wetmore, Jelly Roll, and co-writing Megan Moroney’s Cloud 9. Carter Faith debut, Cherry Valley (on Gatsby) is out now.
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Photo Credit: Meri Grey
