Writer’s Room: Jessie Jo Dillon—“What Would My Dad Say?”

Written by Jessie Jo Dillon

When I began writing songs, I often thought: ‘What would my Dad say? How would he express it? How would he sing it? How would he write this song?’There was rarely a writing room in my early days when he wasn’t brought up, and I’m still often asked about him. After all, he is Dean Dillon, Country Music Hall of Fame inductee, BMI Icon, Nashville Songwriter’s Hall of Fame member, writer of all our favorite George Strait songs, and my hero. The bar will always be high. ‘What would my Dad say?’

As I ground away on Music Row with some hits and misses, it became more apparent to me that my father and all my favorite writers were so great because they had their own perspectives. They were unique, honest, emotional, and vulnerable. They didn’t chase the ever-changing trends of music. They dug deep, worked hard, built relationships, and supported artists by aiding them in telling their stories. Discovering my own point of view has been such a treacherous yet beautiful journey, and I think it’ll continue to be until I lay down my pen for the last time. It has led me to three Grammy Awards nominations, AIMP Songwriter of the Year, an ACM Awards nomination with songs like Dan + Shay and Justin Bieber’s “10,000 Hours,” and also a lot of gut punches, dead-ends, and albatrosses along the way. As I sit and write this, I feel surprisingly content with myself and surer of who I am and my own distinct writing style than I’ve ever realized, and it’s helped create some beautiful songs. 

“Break Up in the End”
Written by Jessie Jo Dillon, Chase McGill & Jon Nite
Recorded by Cole Swindell

I once saw a book in the library titled “John Dies at the End” and thought that was so incredible to give something away like that. It rolled around in my brain for weeks before the idea of “We Break Up in the End” came to me. Chase and Jon are dear friends and collaborators, but I thought the idea might be too depressing and wasn’t sure if I should throw it out in our write. I decided to trust myself and told them the idea anyway and we wrote what I think will always be one of my favorite songs I’ll ever be part of. I remember worrying it was too slow and sad until Cole wanted the song. It went number one on country radio, received award nominations, and showed me in a big way that my vantage point can bring success and connect with the masses because, after all, we’ve all loved and lost. 

“Buried”
Written by Brandy Clark & Jessie Jo Dillon
Recorded by Brandy Clark

I remember being at Brandy’s house in her writing room. My heart was so broken, and I desperately needed to get it out of me. Brandy had also had her share of heartbreak in life, and she had the title “If You Don’t Love Me Anymore.” Once we bled out and finished the song, Brandi Carlile had the brilliant idea to just call it “Buried.” I don’t know if I’ve ever felt more naked than co-writing that song as evident in the last lines: I’ll meet somebody else… probably get married… and I’ll keep it to myself… but I’ll love you ’til I’m buried. This experience reminded me to always write from my heart, even when it hurts and scares me.

“Girl in the Mirror”
Written by Megan Moroney, Jessie Jo Dillon & Matt Jenkins
Recorded by Megan Moroney

I first met Megan when we wrote this, and we bonded instantly. She’s an important artist with a vision. We shared in the painful complexity of being a strong woman, yet sometimes being guilty of making ourselves smaller for a man. Witnessing thousands of people sing along to a song written so unguarded, touches my soul in a way I almost can’t describe. You can’t love the boy more than you love the girl in the mirror…

“Memory Lane”
Written by Matthew Ramsey, Trevor Rosen, Brad Tursi & Jessie Jo Dillon
Recorded by Old Dominion

This one poured out of us in probably under two hours and is my latest number-one song. It was written around the same time I wrote “Buried” and I know exactly the house I am picturing when we settled on… “If I could buy a house on memory lane…”

I still ask myself ‘What would my Dad Say?’ Except now, it sounds more like ‘Does he feel me and hear my thread in this song? Did my co-writers and I land the hook how WE set out to land it? Is the song honest? Would he be proud of me and proud of this song?’ So, to any aspiring songwriters who ever get stuck, whether it’s your dad, your heroes, or both looking over your shoulder in your mind, remember to be true and to be yourself. That alone will make them proud. 

Photo by Jason Kempin/Getty Images for ACM